Applied Chemistry Department, Sardar Vallabhbhai National Institute of Technology, Surat-395 007, India antihypertensive drug oxazoline hydrolysis Suzuki coupling Telmisartan An efficient synthesis of the angiotensin II receptor antagonist Telmisartan ( 1 ) is presented involving a cross coupling of 4-formylphenylboronic acid 10 with 2-(2-bromophenyl)-4,4-dimethyl-2-oxazoline ( 11 ) as the key step (90% yield). The benzimidazole moiety 15 was constructed regioselectively via a reductive amination-condensation sequence, replacing the alkylation of the preformed benzimidazole step in the previously published route. This methodology overcomes many of drawbacks associated with previously reported syntheses.

Telmisartan ( 1 ) is an angiotensin II receptor antagonist useful in the treatment of hypertension, heart diseases, heart attack, and bladder diseases . Telmisartan is currently available in the market as an antihypertensive drug under the brand name of Micardis ® . Essential hypertension is a major risk factor in cardiovascular diseases and is responsible for one-third of global deaths. Most antihypertensive drugs interact with the renin-angiotensin system (RAS), which is the central regulator of blood pressure and electrolyte homeostasis. Renin transforms angiotensinogen into the decapeptide angiotensin I, which is converted by the angiotensin conversion enzyme (ACE) into the octapeptide angiotensin II. The latter binds to its angiotensin receptor (AT 1 ) and, thereby, becomes a powerful vasoconstrictor. In the early 1990s, Merck introduced the non-peptidic orally active angiotensin II receptor antagonist losartan (Lozaar) as the first member of a new class of antihypertensive drugs called sartans, all of which contain a characteristic ortho functionalized biaryl moiety. Telmisartan ( 1 , Boehringer Ingelheim, Micardis ® ) ( ) is an important member of this class of top-selling drugs because it has the strongest binding affinity to the AT 1 receptor, an excellent bioavailability, and a once-per-day dosage. The first total synthesis of Telmisartan as introduced by Ries et al. ( ) starts with the acylation of 4-amino-3-methylbenzoic acid methyl ester ( 2 ) with butyryl chloride, followed by nitration, reduction of the nitro group, and subsequent cyclization of the resulting amine to the benzimidazole derivative 3 . After saponification, the free carboxyl group is condensed with N -methyl-1,2-phenylenediamine to afford the bis-benzimidazole 4 , which is then alkylated with the 4′-(bromomethyl)-2-biphenylcarboxylic acid tert -butyl ester ( 8 ) to give, after hydrolysis of the ester group, Telmisartan ( 1 ) in 21% overall yield and with eight steps as the longest sequence . Several improvements to the above reaction sequence have been reported, e.g., the use of KOH instead of potassium tert -butoxide in the penultimate step and the use of methanolic HCl solution instead of trifluoroacetic acid in the final step . However, the main shortcomings of the synthesis remained, namely, the unsatisfactory regioselectivity in the alkylation of 8 with 4 and the intricate synthesis of the biaryl intermediate 7 . In the original protocol, the latter was synthesized via an Ullmann coupling of the aryl iodides 5 and 6 using 5 equiv of copper . Modern syntheses of 7 involve cross-couplings of sensitive aryl magnesium , zinc , or boron compounds with alkyl 2-halobenzoates. Since the commercialization of Telmisartan, 7 has become readily available at low cost, so that most subsequent published procedures start from this compound. In designing an alternative synthesis of Telmisartan our goal was to minimize the use of expensive and hazardous metals, circumvent the bromination step, and increase the overall efficiency of the synthesis. This was accomplished by reversing the order of the major bond disconnections. We realized biaryl synthesis and reductive amination are the key steps, and have the potential to overcome both of these weaknesses.

We identified 4-formylphenylboronic acid ( 10 ) and 2-(2-bromophenyl)-4,4-dimethyl-2-oxazoline ( 11 ) as the ideal starting materials for the preparation of the key biaryl intermediate. Thus, Suzuki coupling of 2-(2-bromophenyl)-4,4-dimethyl-2-oxazoline with 4-formylphenylboronic acid in presence of aqueous sodium carbonate and tetrakis(triphenylphosphine)palladium(0) in THF solvent gave 2’-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)biphenyl-4-carbaldehyde ( 12 ) in over 90% yield ( ). The reductive amination of the biaryl aldehyde 12 with amine 13 (prepared by the literature procedure ) was carried out in the presence of p -toluenesulfonic acid in toluene and followed by hydrogenation in methyl alcohol. The resulting amine 14 was not isolated but cyclized in situ to the n -propyl benzimidazole 15 in 80% yield in refluxing glacial acetic acid. Finally, cleavage of the oxazoline moiety in 15 by acid afforded Telmisartan ( 1 ) ( ).

In conclusion, a concise and selective synthesis of the antihypertensive drug Telmisartan has been developed, featuring a Suzuki cross-coupling for the construction of the biaryl moiety and a regiospecific reductive amination-condensation sequence for the synthesis of the central benzimidazole.

All solvents and reagents were purchased from the commercial suppliers and used without further purification. All non-aqueous reactions were performed in dry glassware under an atmosphere of dry nitrogen. Organic solutions were concentrated under reduced pressure. Thin layer chromatography was performed on Merck precoated Silica-gel 60F 254 plates. 1 H and 13 C NMR spectra were recorded in DMSO- d 6 and CDCl 3 using 400 MHz, on a Varian Gemini 400 MHz FT NMR spectrometer. The chemical shifts were reported in δ ppm relative to TMS (tetramethylsilane). The IR spectra were recorded in the solid state as KBr dispersion using Perkin Elmer FT-IR spectrophotometer. The mass spectra were recorded on Shimadzu LCMS-QP 800 LC-MS and AB-4000 Q-trap LC-MS/MS. Melting points were obtained by using the open capillary method and are uncorrected. 2’-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)biphenyl-4-carbaldehyde (12): To a mixture of 4-formylphenylboronic acid ( 10 ) (5.0 g, 0.032 mol) and 2-(2-bromophenyl)-4,4-dimethyl-2-oxazoline ( 11 ) (10.1 g, 0.039 mol) in tetrahydrofuran (50.0 mL), 2 M aqueous sodium carbonate solution (20.0 mL) was added at room temperature. The resulting biphasic solution was degassed with nitrogen gas for 20 min. Tetrakis(triphenylphosphine)palladium(0) (0.25 g) was added and heated to reflux (64 °C). The reaction mixture was maintained under reflux for 12 h. After completion of the reaction, the reaction mixture was cooled to 26 °C and saturated ammonium chloride solution (50 mL) and ethyl acetate (50 mL) added. The organic layer was separated, washed twice with water (50.0 mL), dried over sodium sulfate and evaporated under vacuum. The residue was chromatographed on silica gel eluting with hexane/ethyl acetate 80:20 to give the title compound 12 as an oil (8.0 g, 90%); 1 H NMR (400 MHz, DMSO- d 6 ) (δ ppm): 10.0 (1H, s, -CHO), 7.91 (2H, d, J = 8.4 Hz, ArH), 7.73 (1H, d, J = 8.4 Hz, ArH), 7.48 (2H, d, J = 7.8 Hz, ArH), 7.44–7.34 (2H, m, ArH), 7.30 (1H, m, J = 7.4 Hz, ArH), 3.80 (2H, s, -CH 2 ), 1.12 (6H, s, 2 × -CH 3 ); 13 C NMR (100 MHz, DMSO- d 6 ) (δ ppm); 28.0, 68.0, 78.9, 128.0, 128.5, 129.5, 129.6, 130.4, 130.5, 131.2, 135.3, 140.2, 147.0, 161.8, 193.2.; MS ( m/z ): 280 [M + + 1]. 3'-{[2'-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)biphenyl-4-yl]methyl}-1,7'-dimethyl-2'-propyl-1 H ,3' H -2,5'-bibenzimidazole (15) : A mixture of 13 (4.0 g, 0.01 mol), 12 (3.5 g, 0.01 mol), and p -TsOH (0.21 g, 0.001 mol) was suspended in toluene (40 mL) under nitrogen, and the mixture refluxed for 16 h and then concentrated. The residue was diluted with methanol (40 mL) and transferred to a stainless steel autoclave. Palladium on charcoal (10%, 1.0 g) was added and the reaction mixture stirred under H 2 pressure (7 bar) for 24 h at 60 °C. After cooling to room temperature and filtration, the filter cake was rinsed with ethyl acetate (3 × 50 mL). The filtrate was washed with water, and the aqueous layer basified to pH 10 with aqueous ammonia and extracted with ethyl acetate (2 × 50 mL). The combined organic layers were dried over MgSO 4 and concentrated. The crude amine 14 was diluted with glacial acetic acid (40 mL), the resulting solution refluxed for 2 h and then concentrated. Water (150 mL) was added to residue. The product was extracted twice with ethyl acetate (2 × 50 mL) and evaporated under vacuum at 55 °C. The residue was triturated with n -hexane (40 mL) to yield a solid which was removed by filtration and dried at 50–55 °C for 3–4 h to afford 15 as a white crystalline powder (yield 5.7 g, 80% yield); melting point 191–193 °C; IR (KBr, cm -1 ) 1630 (C=N); HRMS m/z calculated for C 37 H 37 N 5 O – 568.7225 [M + 1], found – 568.7222; 1 H NMR (400 MHz, CDCl 3 ) (δ ppm): 7.78 (1H, d, J = 8.0 Hz, ArH), 7.68 (1H, m, J = 8.0 Hz, ArH), 7.47–7.26 (10H, m, ArH), 7.07 (2H, m, J = 8.0 Hz, ArH), 5.45 (2H, s, -CH 2 ), 3.82 (3H, s, -CH 3 ), 3.58 (2H, s, -CH 2 ), 2.97 (2H, t, J = 7.6 Hz, -CH 2 ), 2.74 (3H, s, -CH 3 ), 1.92 (2H, m , J = 7.6 Hz, -CH 2 ), 1.29 (6H, s, 2 x -CH 3 ), 1.04 (3H, t, J = 7.6 Hz, -CH 3 ); 13 C NMR (100 MHz, CDCl 3 ) (δ ppm): 13.9, 16.7, 21.6, 27.6, 29.6, 31.6, 46.9, 67.2, 79.0, 108.8, 109.2, 119.3, 122.1, 122.2, 123.5, 123.6, 125.6, 127.0, 127.2, 128.8, 129.1, 129.7, 129.9, 130.2, 134.4, 134.8, 136.4, 140.6, 140.8, 142.6, 142.8, 154.2, 156.2, 163.1. 4’-[(1,7’-dimethyl-2’-propyl-1 H ,3’ H -2,5’-bibenzimidazol-3’-yl)methyl]biphenyl -2-carboxylic acid (1) : A mixture of 15 (4.0 g, 0.007 mol) and concentrated hydrochloric acid (40 mL) was heated at reflux (100–110 °C) for about 30 h. The reaction mass was cooled to 0–5 °C. Sodium hydroxide solution (20%) was added until the pH of the reaction mixture was 9–10 and then stirred at room temperature for a further 2 h. The resulting solid was removed by filtration and washed with water (50 mL). The wet cake was dissolved in a mixture of water (60 mL) and acetonitrile (20 mL) and then heated to 60–65 °C. The pH of the resulting clear solution was adjusted to 5.0–5.5 with 5% acetic acid, and stirring continued for 2 h. The precipitated solid was filtered and washed with water (50 mL). After drying at 70–75 °C for 4–5 h under a vacuum Telmisartan ( 1 ) was obtained as a white crystalline powder (yield 2.9 g, 80%); melting point: 260–262 °C (lit mp 260–262 °C); IR (KBr, cm -1 ) 2300–3500 (broad), 1680 (C=O); HRMS m/z calculated for C 33 H 30 N 4 O 2 – 515.6169 [M + 1], found – 515.6192; 1 H NMR (400 MHz, CDCl 3 ) (δ ppm): 12.8 (1H, s, -COOH), 8.42 (1H, d, J = 8.0 Hz, ArH), 8.02 (1H, d, J = 8.0 Hz, ArH), 7.50–7.26 (8H, m, ArH), 7.20 (2H, d, J = 8.0 Hz, ArH), 7.05 (1H, s, ArH), 6.96 (1H, s, ArH), 5.42 (2H, s, -CH 2 ), 3.82 (3H, s, -CH 3 ), 2.97 (2H, t, J = 7.6 Hz, -CH 2 ), 2.74 (3H, s, -CH 3 ), 1.92 (2H, m, J = 7.6 Hz, -CH 2 ), 1.04 (3H, t, J = 7.6 Hz, -CH 3 ); 13 C NMR (100 MHz, DMSO- d 6 ) (δ ppm): 13.5, 16.7, 20.6, 27.6, 32.7, 47.1, 51.7, 112.0, 112.7, 114.7, 118.6, 125.3, 125.7, 125.8, 127.0, 127.4, 128.6, 129.3, 130.4, 130.6, 131.5, 132.3, 133.1, 133.2, 133.7, 134.5, 140.2, 140.5, 150.2, 157.3, 168.1.

The angiotensin II receptor antagonist Telmisartan.

First literature synthesis of Telmisartan (a) n PrCOCl, C 6 H 5 Cl, 100 °C (b) HNO 3 /H 2 SO 4 , 0 °C (c) Pd/C, 5 bar, H 2, MeOH (d) AcOH, 120 °C, yield: 78% (e) NaOH, MeOH/H 2 O, 100 °C (f) 2-MeNH-C 6 H 4 -NH 2 , PPA, 150 °C, yield: 64% (g) t BuOK, DMSO, RT (h) TFA, DCM, RT, yield: 42% (i) Cu (5 equiv), 210 °C, (j) HCl, H 2 O, 100 °C (k) (COCl) 2 , DCM, 0 °C, (l) t BuOK, THF, RT, yield: 9% (m) NBS, (PhCOO) 2 , CCl 4 , 76 °C. (a) Pd(PPh 3 ) 4 , aq Na 2 CO 3 , THF, 12.0 h, 90%. (a) p-TsOH, toluene, 110 °C, 12 h, (b) Pd/C, 7 bar H 2, MeOH, 60 °C, 24 h, 100% (c) AcOH, 120 °C, 2 h, 80% (d) Conc. HCl, 100–110 °C, 30 h, 80%. RMMXLENWKUUMAY-UHFFFAOYSA-N InChI=1S/C33H30N4O2/c1-4-9-30-35-31-21(2)18-24(32-34-27-12-7-8-13-28(27)36(32)3)19-29(31)37(30)20-22-14-16-23(17-15-22)25-10-5-6-11-26(25)33(38)39/h5-8,10-19H,4,9,20H2,1-3H3,(H,38,39) CCCC1=NC2=C(C=C(C=C2C)C3=NC4=C(C=CC=C4)N3C)N1CC5=CC=C(C=C5)C6=C(C=CC=C6)C(=O)O C1=CC=C2C(=C1)N=C(N2C)C3=CC4=C(C(=C3)C)N=C(CCC)N4CC5=CC=C(C=C5)C6=CC=CC=C6C(=O)O |(25.42,-38.19,;25.4,-49.88,;35.49,-55.71,;45.57,-49.86,;45.56,-38.12,;35.46,-32.44,;56.68,-34.56,;63.64,-44.06,;56.69,-53.49,;56.55,-65.06,;75.13,-44.01,;80.93,-54.06,;92.42,-54,;98.33,-43.95,;92.34,-33.9,;80.8,-34.01,;98.15,-23.76,;109.59,-46.4,;110.83,-57.85,;120.92,-63.74,;120.93,-75.31,;131.03,-81.12,;100.18,-62.54,;97.79,-73.81,;87.8,-79.58,;77.81,-73.81,;67.81,-79.58,;67.81,-91.12,;77.81,-96.89,;87.8,-91.12,;57.83,-96.88,;47.81,-91.1,;37.8,-96.88,;37.8,-108.45,;47.81,-114.23,;57.83,-108.45,;67.81,-114.21,;67.81,-125.74,;77.79,-108.45,)| AuxInfo=1/1/N:23,20,10,22,33,34,1,2,21,32,35,4,3,26,30,27,29,14,12,24,13,25,28,11,31,36,8,9,17,19,16,6,37,7,15,5,18,38,39/E:(14,15)(16,17)(38,39)/rA:39nCCCCNCNCCCCCCCNCCNCCCCCCCCCCCCCCCCCCCOO/rB:d1;s2;s1;;s5;d6;d4s7;d3s5s8;s5;s6;d11;;s11d13;;s13s15;s12d16;s17;d15s18;s13;s19;s21;s22;s18;s24;d25;s26;d27;s28;s25d29;s28;d31;s32;d33;s34;s31d35;s36;d37;s37;/rC:25,4216,-38,1871,0;25,3995,-49,8762,0;35,4924,-55,7052,0;35,4578,-32,4399,0;56,6936,-53,4882,0;63,6371,-44,0597,0;56,6845,-34,5577,0;45,5619,-38,1176,0;45,5669,-49,8605,0;56,5522,-65,0642,0;75,1343,-44,0097,0;80,9307,-54,0578,0;92,3376,-33,9020,0;80,8014,-34,0123,0;109,5888,-46,3982,0;98,3337,-43,9505,0;92,4180,-54,0039,0;100,1809,-62,5365,0;110,8287,-57,8534,0;98,1473,-23,7629,0;120,9214,-63,7444,0;120,9337,-75,3083,0;131,0262,-81,1196,0;97,7874,-73,8149,0;87,7963,-79,5833,0;77,8053,-73,8149,0;67,8142,-79,5833,0;67,8142,-91,1200,0;77,8053,-96,8883,0;87,7963,-91,1200,0;57,8292,-96,8848,0;47,8133,-91,1021,0;37,7974,-96,8848,0;37,7974,-108,4501,0;47,8133,-114,2328,0;57,8292,-108,4501,0;67,8103,-114,2127,0;67,8103,-125,7379,0;77,7915,-108,4501,0; C33H30N4O2 C(=O)(O)* COOH CDK 04222607282D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 39 44 0 0 0 M V30 BEGIN ATOM M V30 1 C 25.42159 -38.1871 0 0 M V30 2 C 25.39946 -49.87619 0 0 M V30 3 C 35.4924 -55.7052 0 0 M V30 4 C 35.45782 -32.43987 0 0 M V30 5 N 56.69356 -53.48822 0 0 M V30 6 C 63.6371 -44.05972 0 0 M V30 7 N 56.68452 -34.55772 0 0 M V30 8 C 45.56194 -38.11755 0 0 M V30 9 C 45.56694 -49.86049 0 0 M V30 10 C 56.5522 -65.06419 0 0 M V30 11 C 75.13434 -44.0097 0 0 M V30 12 C 80.93068 -54.05779 0 0 M V30 13 C 92.33757 -33.90198 0 0 M V30 14 C 80.80136 -34.01234 0 0 M V30 15 N 109.58879 -46.39819 0 0 M V30 16 C 98.33371 -43.95052 0 0 M V30 17 C 92.41795 -54.00392 0 0 M V30 18 N 100.18092 -62.53647 0 0 M V30 19 C 110.82872 -57.85336 0 0 M V30 20 C 98.14734 -23.76288 0 0 M V30 21 C 120.92139 -63.74437 0 0 M V30 22 C 120.93365 -75.30833 0 0 M V30 23 C 131.02621 -81.11961 0 0 M V30 24 C 97.7874 -73.8149 0 0 M V30 25 C 87.79631 -79.58325 0 0 M V30 26 C 77.80525 -73.8149 0 0 M V30 27 C 67.81416 -79.58325 0 0 M V30 28 C 67.81416 -91.11996 0 0 M V30 29 C 77.80525 -96.88831 0 0 M V30 30 C 87.79631 -91.11996 0 0 M V30 31 C 57.82922 -96.88475 0 0 M V30 32 C 47.81332 -91.10208 0 0 M V30 33 C 37.79744 -96.88475 0 0 M V30 34 C 37.79744 -108.4501 0 0 M V30 35 C 47.81332 -114.23279 0 0 M V30 36 C 57.82922 -108.4501 0 0 M V30 37 C 67.81033 -114.21271 0 0 M V30 38 O 67.81033 -125.73793 0 0 M V30 39 O 77.79147 -108.4501 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 9 M V30 4 2 8 4 M V30 5 1 4 1 M V30 6 1 8 9 M V30 7 2 6 7 M V30 8 1 5 6 M V30 9 1 7 8 M V30 10 1 9 5 M V30 11 1 5 10 M V30 12 1 6 11 M V30 13 2 11 12 M V30 14 1 12 17 M V30 15 1 16 13 M V30 16 2 13 14 M V30 17 1 14 11 M V30 18 2 16 17 M V30 19 1 15 16 M V30 20 1 17 18 M V30 21 2 19 15 M V30 22 1 13 20 M V30 23 1 19 21 M V30 24 1 21 22 M V30 25 1 22 23 M V30 26 1 18 19 M V30 27 1 18 24 M V30 28 1 24 25 M V30 29 2 25 26 M V30 30 1 26 27 M V30 31 2 27 28 M V30 32 1 28 29 M V30 33 2 29 30 M V30 34 1 30 25 M V30 35 1 28 31 M V30 36 2 31 32 M V30 37 1 32 33 M V30 38 2 33 34 M V30 39 1 34 35 M V30 40 2 35 36 M V30 41 1 36 31 M V30 42 2 37 38 M V30 43 1 37 39 M V30 44 1 36 37 M V30 END BOND M V30 END CTAB M END BXXLTVBTDZXPTN-UHFFFAOYSA-N InChI=1S/C8H7IO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,1H3 COC(=O)C1=C(C=CC=C1)I C1=CC=CC(=C1C(=O)OC)I |(24.11,-159.72,;24.11,-171.22,;34.08,-176.98,;44.04,-171.22,;44.04,-159.72,;34.08,-153.96,;34.08,-142.49,;24.15,-136.76,;44.01,-136.76,;44.01,-125.29,;53.98,-153.98,)| AuxInfo=1/0/N:11,2,3,1,4,6,5,7,8,9,10/rA:11nCCCCCCCIOOC/rB:d1;s2;d3;s4;s1d5;s6;s5;d7;s7;s10;/rC:24,1109,-159,7157,0;24,1109,-171,2244,0;34,0777,-176,9787,0;44,0444,-171,2244,0;44,0444,-159,7157,0;34,0777,-153,9614,0;34,0777,-142,4927,0;53,9766,-153,9814,0;24,1455,-136,7583,0;44,0099,-136,7583,0;44,0099,-125,2896,0; C8H7IO2 CDK 04222607282D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 11 11 0 0 0 M V30 BEGIN ATOM M V30 1 C 24.11087 -159.71573 0 0 M V30 2 C 24.11087 -171.22438 0 0 M V30 3 C 34.07765 -176.97871 0 0 M V30 4 C 44.04445 -171.22438 0 0 M V30 5 C 44.04445 -159.71573 0 0 M V30 6 C 34.07765 -153.9614 0 0 M V30 7 C 34.07765 -142.49266 0 0 M V30 8 I 53.97664 -153.98137 0 0 M V30 9 O 24.14546 -136.75832 0 0 M V30 10 O 44.00986 -136.75832 0 0 M V30 11 C 44.00986 -125.28961 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 4 M V30 4 1 4 5 M V30 5 2 5 6 M V30 6 1 6 1 M V30 7 1 6 7 M V30 8 1 5 8 M V30 9 2 7 9 M V30 10 1 7 10 M V30 11 1 10 11 M V30 END BOND M V30 END CTAB M END DEFDQXCQBZEOGY-UHFFFAOYSA-N InChI=1S/C13H16N2O2/c1-4-5-11-14-10-7-9(13(16)17-3)6-8(2)12(10)15-11/h6-7H,4-5H2,1-3H3,(H,14,15) CCCC1=NC2=C(C=C(C=C2C)C(=O)OC)N1 C1=C(C=C2C(=C1C)N=C(N2)CCC)C(OC)=O |(169.63,-40.68,;169.61,-52.23,;179.55,-57.98,;189.55,-52.19,;189.47,-40.61,;179.52,-34.93,;179.47,-23.44,;200.46,-36.96,;207.33,-46.28,;200.59,-55.69,;218.76,-46.27,;226.82,-38.13,;238.32,-38.13,;159.65,-57.96,;149.7,-52.2,;139.76,-57.91,;159.63,-69.45,)| AuxInfo=1/1/N:16,8,17,15,14,1,3,4,2,13,10,12,5,9,11,7,6/rA:17nCCCCCOOCNCNCCCCCC/rB:d1;s2;s1;s2;s5;d5;s4;;s9;d10;d4s11;d3s9s12;s10;s14;s15;s6;/rC:169,6322,-40,6841,0;169,6101,-52,2252,0;179,5535,-57,9802,0;179,5189,-34,9310,0;159,6459,-57,9582,0;149,6988,-52,1954,0;159,6287,-69,4540,0;179,4716,-23,4354,0;200,5880,-55,6917,0;207,3285,-46,2794,0;200,4586,-36,9610,0;189,4734,-40,6144,0;189,5530,-52,1913,0;218,7562,-46,2730,0;226,8193,-38,1302,0;238,3150,-38,1302,0;139,7581,-57,9149,0; C13H16N2O2 CDK 04222607282D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 17 18 0 0 0 M V30 BEGIN ATOM M V30 1 C 169.6322 -40.68407 0 0 M V30 2 C 169.61009 -52.22522 0 0 M V30 3 C 179.5535 -57.98024 0 0 M V30 4 C 179.51891 -34.93103 0 0 M V30 5 C 159.64586 -57.95822 0 0 M V30 6 O 149.69881 -52.19545 0 0 M V30 7 O 159.62868 -69.45403 0 0 M V30 8 C 179.47162 -23.43536 0 0 M V30 9 N 200.58801 -55.6917 0 0 M V30 10 C 207.32849 -46.27943 0 0 M V30 11 N 200.45863 -36.96097 0 0 M V30 12 C 189.47345 -40.61444 0 0 M V30 13 C 189.55299 -52.19127 0 0 M V30 14 C 218.75623 -46.27304 0 0 M V30 15 C 226.81926 -38.13019 0 0 M V30 16 C 238.31502 -38.13019 0 0 M V30 17 C 139.75806 -57.91493 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 13 M V30 4 2 12 4 M V30 5 1 4 1 M V30 6 1 2 5 M V30 7 1 5 6 M V30 8 2 5 7 M V30 9 1 4 8 M V30 10 1 12 13 M V30 11 2 10 11 M V30 12 1 9 10 M V30 13 1 11 12 M V30 14 1 13 9 M V30 15 1 10 14 M V30 16 1 14 15 M V30 17 1 15 16 M V30 18 1 6 17 M V30 END BOND M V30 END CTAB M END ILXRSCZVHSZGCS-UHFFFAOYSA-N InChI=1S/C19H20N4/c1-4-7-17-20-15-11-13(10-12(2)18(15)22-17)19-21-14-8-5-6-9-16(14)23(19)3/h5-6,8-11H,4,7H2,1-3H3,(H,20,22) CCCC1=NC2=C(C=C(C=C2C)C3=NC4=C(C=CC=C4)N3C)N1 C1=CC=C2C(=C1)N=C(N2C)C3=CC4=C(C(=C3)C)N=C(CCC)N4 |(298.33,-41.6,;298.31,-53.22,;308.34,-58.97,;318.34,-53.2,;318.34,-41.53,;308.3,-35.84,;329.39,-37.96,;336.27,-47.39,;329.4,-56.75,;329.26,-68.26,;347.7,-47.34,;353.5,-57.32,;364.92,-57.27,;370.76,-47.29,;364.84,-37.31,;353.37,-37.42,;370.57,-27.24,;381.95,-49.74,;383.19,-61.12,;393.21,-66.94,;393.22,-78.44,;403.25,-84.25,;372.61,-65.81,)| AuxInfo=1/1/N:23,20,10,22,1,2,21,4,3,14,12,13,11,8,17,9,19,16,6,18,7,15,5/rA:23nCCCCNCNCCCCCCCNCCNCCCCC/rB:d1;s2;s1;;s5;d6;d4s7;d3s5s8;s5;s6;d11;;s11d13;;s13s15;s12d16;s17;d15s18;s13;s19;s21;s22;/rC:298,3349,-41,5961,0;298,3128,-53,2171,0;308,3360,-58,9721,0;308,3014,-35,8431,0;329,3988,-56,7529,0;336,2695,-47,3948,0;329,3898,-37,9631,0;318,3358,-41,5265,0;318,3408,-53,2014,0;329,2573,-68,2607,0;347,6984,-47,3447,0;353,5005,-57,3230,0;364,8391,-37,3067,0;353,3712,-37,4171,0;381,9480,-49,7356,0;370,7614,-47,2855,0;364,9195,-57,2691,0;372,6105,-65,8102,0;383,1892,-61,1224,0;370,5748,-27,2372,0;393,2121,-66,9395,0;393,2244,-78,4353,0;403,2473,-84,2524,0; C19H20N4 CDK 04222607282D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 23 26 0 0 0 M V30 BEGIN ATOM M V30 1 C 298.3349 -41.5961 0 0 M V30 2 C 298.31277 -53.21707 0 0 M V30 3 C 308.336 -58.97211 0 0 M V30 4 C 308.30142 -35.84309 0 0 M V30 5 N 329.3988 -56.75288 0 0 M V30 6 C 336.26947 -47.39478 0 0 M V30 7 N 329.38977 -37.96306 0 0 M V30 8 C 318.33582 -41.52646 0 0 M V30 9 C 318.34082 -53.20137 0 0 M V30 10 C 329.25726 -68.26068 0 0 M V30 11 C 347.69843 -47.34473 0 0 M V30 12 C 353.50055 -57.323 0 0 M V30 13 C 364.83908 -37.30669 0 0 M V30 14 C 353.37115 -37.41711 0 0 M V30 15 N 381.948 -49.7356 0 0 M V30 16 C 370.76141 -47.28548 0 0 M V30 17 C 364.91949 -57.26912 0 0 M V30 18 N 372.6105 -65.81024 0 0 M V30 19 C 383.18918 -61.12242 0 0 M V30 20 C 370.57483 -27.23723 0 0 M V30 21 C 393.21207 -66.9395 0 0 M V30 22 C 393.22437 -78.43526 0 0 M V30 23 C 403.24725 -84.25237 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 9 M V30 4 2 8 4 M V30 5 1 4 1 M V30 6 1 8 9 M V30 7 2 6 7 M V30 8 1 5 6 M V30 9 1 7 8 M V30 10 1 9 5 M V30 11 1 5 10 M V30 12 1 6 11 M V30 13 2 11 12 M V30 14 1 12 17 M V30 15 1 16 13 M V30 16 2 13 14 M V30 17 1 14 11 M V30 18 2 16 17 M V30 19 1 15 16 M V30 20 1 17 18 M V30 21 2 19 15 M V30 22 1 13 20 M V30 23 1 19 21 M V30 24 1 21 22 M V30 25 1 22 23 M V30 26 1 18 19 M V30 END BOND M V30 END CTAB M END JSCFLEBEWCTASN-UHFFFAOYSA-N InChI=1S/C37H38N4O2/c1-7-12-33-39-34-24(2)21-27(35-38-30-15-10-11-16-31(30)40(35)6)22-32(34)41(33)23-25-17-19-26(20-18-25)28-13-8-9-14-29(28)36(42)43-37(3,4)5/h8-11,13-22H,7,12,23H2,1-6H3 CCCC1=NC2=C(C=C(C=C2C)C3=NC4=C(C=CC=C4)N3C)N1CC5=CC=C(C=C5)C6=C(C=CC=C6)C(=O)OC(C)(C)C C1=CC=C2C(=C1)N=C(N2C)C3=CC4=C(C(=C3)C)N=C(CCC)N4CC5=CC=C(C=C5)C6=CC=CC=C6C(=O)OC(C)(C)C |(309.43,-232.48,;309.4,-244.11,;319.45,-249.91,;329.47,-244.1,;329.47,-232.41,;319.41,-226.76,;340.54,-228.87,;347.45,-238.33,;340.54,-247.71,;340.4,-259.23,;358.89,-238.28,;364.66,-248.28,;376.09,-248.22,;381.98,-238.22,;376.01,-228.22,;364.53,-228.33,;381.79,-218.13,;393.18,-240.65,;394.41,-252.05,;404.46,-257.91,;404.47,-269.42,;414.51,-275.2,;383.82,-256.71,;381.44,-267.94,;371.49,-273.68,;361.55,-267.94,;351.61,-273.68,;351.61,-285.16,;361.55,-290.9,;371.49,-285.16,;341.67,-290.89,;331.71,-285.14,;321.74,-290.89,;321.74,-302.4,;331.71,-308.16,;341.67,-302.4,;351.61,-308.14,;361.54,-302.4,;351.61,-319.6,;361.54,-325.34,;361.54,-336.81,;371.47,-319.6,;371.51,-331.09,)| AuxInfo=1/0/N:23,20,41,42,43,10,22,33,34,1,2,21,32,35,4,3,26,30,27,29,14,12,24,13,25,28,11,31,36,8,9,17,19,16,6,37,40,7,15,5,18,38,39/E:(3,4,5)(17,18)(19,20)/rA:43nCCCCNCNCCCCCCCNCCNCCCCCCCCCCCCCCCCCCCOOCCCC/rB:d1;s2;s1;;s5;d6;d4s7;d3s5s8;s5;s6;d11;;s11d13;;s13s15;s12d16;s17;d15s18;s13;s19;s21;s22;s18;s24;d25;s26;d27;s28;s25d29;s28;d31;s32;d33;s34;s31d35;s36;d37;s37;s39;s40;s40;s40;/rC:309,4254,-232,4826,0;309,4034,-244,1144,0;319,4469,-249,9148,0;319,4125,-226,7635,0;340,5441,-247,7087,0;347,4536,-238,3264,0;340,5351,-228,8710,0;329,4670,-232,4133,0;329,4720,-244,0987,0;340,4034,-259,2279,0;358,8945,-238,2766,0;364,6624,-248,2754,0;376,0134,-228,2184,0;364,5338,-228,3282,0;393,1801,-240,6534,0;381,9801,-238,2177,0;376,0934,-248,2218,0;383,8183,-256,7126,0;394,4139,-252,0524,0;381,7947,-218,1290,0;404,4571,-257,9146,0;404,4693,-269,4218,0;414,5124,-275,2046,0;381,4365,-267,9357,0;371,4944,-273,6758,0;361,5523,-267,9357,0;351,6102,-273,6758,0;351,6102,-285,1559,0;361,5523,-290,8960,0;371,4944,-285,1559,0;341,6742,-290,8925,0;331,7074,-285,1382,0;321,7406,-290,8925,0;321,7406,-302,4012,0;331,7074,-308,1555,0;341,6742,-302,4012,0;351,6064,-308,1355,0;361,5386,-302,4012,0;351,6064,-319,6042,0;361,5386,-325,3386,0;361,5386,-336,8073,0;371,4708,-319,6042,0;371,5054,-331,0929,0; C37H38N4O2 CDK 04222607282D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 43 48 0 0 0 M V30 BEGIN ATOM M V30 1 C 309.42542 -232.48256 0 0 M V30 2 C 309.40338 -244.11436 0 0 M V30 3 C 319.44687 -249.91478 0 0 M V30 4 C 319.41248 -226.76349 0 0 M V30 5 N 340.54413 -247.70866 0 0 M V30 6 C 347.45361 -238.32639 0 0 M V30 7 N 340.5351 -228.87096 0 0 M V30 8 C 329.46704 -232.41335 0 0 M V30 9 C 329.47205 -244.09872 0 0 M V30 10 C 340.40344 -259.22791 0 0 M V30 11 C 358.8945 -238.27661 0 0 M V30 12 C 364.66241 -248.27544 0 0 M V30 13 C 376.01337 -228.21844 0 0 M V30 14 C 364.53375 -228.32825 0 0 M V30 15 N 393.18005 -240.6534 0 0 M V30 16 C 381.98013 -238.21773 0 0 M V30 17 C 376.09338 -248.22185 0 0 M V30 18 N 383.8183 -256.71255 0 0 M V30 19 C 394.41391 -252.05241 0 0 M V30 20 C 381.79468 -218.12903 0 0 M V30 21 C 404.45709 -257.91455 0 0 M V30 22 C 404.4693 -269.42181 0 0 M V30 23 C 414.51239 -275.20462 0 0 M V30 24 C 381.43652 -267.93573 0 0 M V30 25 C 371.49442 -273.67578 0 0 M V30 26 C 361.55231 -267.93573 0 0 M V30 27 C 351.6102 -273.67578 0 0 M V30 28 C 351.6102 -285.15594 0 0 M V30 29 C 361.55231 -290.89603 0 0 M V30 30 C 371.49442 -285.15594 0 0 M V30 31 C 341.67419 -290.89252 0 0 M V30 32 C 331.7074 -285.13818 0 0 M V30 33 C 321.7406 -290.89252 0 0 M V30 34 C 321.7406 -302.40118 0 0 M V30 35 C 331.7074 -308.15552 0 0 M V30 36 C 341.67419 -302.40118 0 0 M V30 37 C 351.60638 -308.1355 0 0 M V30 38 O 361.53857 -302.40115 0 0 M V30 39 O 351.60641 -319.60422 0 0 M V30 40 C 361.53857 -325.33856 0 0 M V30 41 C 361.5386 -336.80725 0 0 M V30 42 C 371.47076 -319.60419 0 0 M V30 43 C 371.50537 -331.0929 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 9 M V30 4 2 8 4 M V30 5 1 4 1 M V30 6 1 8 9 M V30 7 2 6 7 M V30 8 1 5 6 M V30 9 1 7 8 M V30 10 1 9 5 M V30 11 1 5 10 M V30 12 1 6 11 M V30 13 2 11 12 M V30 14 1 12 17 M V30 15 1 16 13 M V30 16 2 13 14 M V30 17 1 14 11 M V30 18 2 16 17 M V30 19 1 15 16 M V30 20 1 17 18 M V30 21 2 19 15 M V30 22 1 13 20 M V30 23 1 19 21 M V30 24 1 21 22 M V30 25 1 22 23 M V30 26 1 18 19 M V30 27 1 18 24 M V30 28 1 24 25 M V30 29 2 25 26 M V30 30 1 26 27 M V30 31 2 27 28 M V30 32 1 28 29 M V30 33 2 29 30 M V30 34 1 30 25 M V30 35 1 28 31 M V30 36 2 31 32 M V30 37 1 32 33 M V30 38 2 33 34 M V30 39 1 34 35 M V30 40 2 35 36 M V30 41 1 36 31 M V30 42 1 36 37 M V30 43 2 37 38 M V30 44 1 37 39 M V30 45 1 39 40 M V30 46 1 40 41 M V30 47 1 40 42 M V30 48 1 40 43 M V30 END BOND M V30 END CTAB M END OWEDFWZJRNPJIV-UHFFFAOYSA-N InChI=1S/C18H20O2/c1-13-9-11-14(12-10-13)15-7-5-6-8-16(15)17(19)20-18(2,3)4/h5-12H,1-4H3 CC1=CC=C(C=C1)C2=C(C=CC=C2)C(=O)OC(C)(C)C C1=CC(=CC=C1C)C2=CC=CC=C2C(=O)OC(C)(C)C |(176.29,-126.28,;176.27,-137.98,;186.21,-143.74,;196.35,-137.97,;196.29,-126.21,;186.18,-120.45,;186.13,-108.87,;186.21,-155.3,;176.26,-161.09,;176.25,-172.65,;186.2,-178.41,;196.35,-172.6,;196.31,-161.06,;206.21,-155.21,;206.1,-143.6,;216.16,-161.01,;226.14,-155.1,;231.8,-145.04,;234.2,-163.24,;237.71,-155.1,)| AuxInfo=1/0/N:7,18,19,20,10,11,9,12,1,5,2,4,6,3,8,13,14,17,15,16/E:(2,3,4)(9,10)(11,12)/rA:20nCCCCCCCCCCCCCCOOCCCC/rB:d1;s2;d3;s4;s1d5;s6;s3;d8;s9;d10;s11;s8d12;s13;d14;s14;s16;s17;s17;s17;/rC:176,2931,-126,2792,0;176,2710,-137,9801,0;186,2144,-143,7351,0;196,3488,-137,9709,0;196,2940,-126,2096,0;186,1798,-120,4464,0;186,1325,-108,8709,0;186,2105,-155,3037,0;176,2581,-161,0880,0;176,2494,-172,6459,0;186,2045,-178,4052,0;196,3487,-172,6024,0;196,3084,-161,0635,0;206,2096,-155,2150,0;206,0978,-143,6035,0;216,1566,-161,0069,0;226,1356,-155,0993,0;231,8037,-145,0405,0;234,1986,-163,2421,0;237,7113,-155,0993,0; C18H20O2 CDK 04222607282D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 20 21 0 0 0 M V30 BEGIN ATOM M V30 1 C 176.29311 -126.27924 0 0 M V30 2 C 176.27101 -137.98007 0 0 M V30 3 C 186.21442 -143.73509 0 0 M V30 4 C 196.34875 -137.9709 0 0 M V30 5 C 196.29402 -126.20961 0 0 M V30 6 C 186.17982 -120.44638 0 0 M V30 7 C 186.13251 -108.87086 0 0 M V30 8 C 186.21054 -155.30367 0 0 M V30 9 C 176.25815 -161.08804 0 0 M V30 10 C 176.2494 -172.64592 0 0 M V30 11 C 186.20453 -178.40518 0 0 M V30 12 C 196.34872 -172.60243 0 0 M V30 13 C 196.30838 -161.06351 0 0 M V30 14 C 206.20963 -155.21497 0 0 M V30 15 O 206.09784 -143.6035 0 0 M V30 16 O 216.15665 -161.00685 0 0 M V30 17 C 226.13564 -155.09927 0 0 M V30 18 C 231.80368 -145.04047 0 0 M V30 19 C 234.19864 -163.24213 0 0 M V30 20 C 237.71126 -155.09927 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 4 M V30 4 1 4 5 M V30 5 2 5 6 M V30 6 1 6 1 M V30 7 1 6 7 M V30 8 1 3 8 M V30 9 2 8 9 M V30 10 1 9 10 M V30 11 2 10 11 M V30 12 1 11 12 M V30 13 2 12 13 M V30 14 1 13 8 M V30 15 1 13 14 M V30 16 2 14 15 M V30 17 1 14 16 M V30 18 1 16 17 M V30 19 1 17 18 M V30 20 1 17 19 M V30 21 1 17 20 M V30 END BOND M V30 END CTAB M END UDHAWRUAECEBHC-UHFFFAOYSA-N InChI=1S/C7H7I/c1-6-2-4-7(8)5-3-6/h2-5H,1H3 CC1=CC=C(C=C1)I C1=C(C=CC(=C1)I)C |(84.65,-153.12,;84.65,-164.63,;94.62,-170.39,;104.58,-164.63,;104.58,-153.12,;94.62,-147.37,;114.52,-147.39,;74.72,-170.37,)| AuxInfo=1/0/N:8,1,3,6,4,2,5,7/E:(2,3)(4,5)/rA:8nCCCCCCIC/rB:d1;s2;d3;s4;s1d5;s5;s2;/rC:84,6513,-153,1222,0;84,6513,-164,6309,0;94,6180,-170,3852,0;104,5848,-164,6309,0;104,5848,-153,1222,0;94,6180,-147,3679,0;114,5170,-147,3878,0;74,7191,-170,3652,0; C7H7I CDK 04222607282D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 8 8 0 0 0 M V30 BEGIN ATOM M V30 1 C 84.65126 -153.12221 0 0 M V30 2 C 84.65126 -164.63087 0 0 M V30 3 C 94.61804 -170.38519 0 0 M V30 4 C 104.58484 -164.63087 0 0 M V30 5 C 104.58484 -153.12221 0 0 M V30 6 C 94.61804 -147.36787 0 0 M V30 7 I 114.51703 -147.38785 0 0 M V30 8 C 74.71906 -170.36522 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 4 M V30 4 1 4 5 M V30 5 2 5 6 M V30 6 1 6 1 M V30 7 1 5 7 M V30 8 1 2 8 M V30 END BOND M V30 END CTAB M END YHXCWNQNVMAENQ-UHFFFAOYSA-N InChI=1S/C18H19BrO2/c1-18(2,3)21-17(20)16-7-5-4-6-15(16)14-10-8-13(12-19)9-11-14/h4-11H,12H2,1-3H3 CC(C)(C)OC(=O)C1=C(C=CC=C1)C2=CC=C(C=C2)CBr C1=CC(=CC=C1CBr)C2=CC=CC=C2C(=O)OC(C)(C)C |(287.83,-126.97,;287.81,-138.67,;297.75,-144.42,;307.88,-138.66,;307.83,-126.9,;297.72,-121.13,;297.67,-109.56,;305.82,-101.42,;297.75,-155.99,;287.79,-161.77,;287.78,-173.33,;297.74,-179.09,;307.88,-173.29,;307.84,-161.75,;317.74,-155.9,;317.63,-144.29,;327.69,-161.69,;337.67,-155.79,;343.34,-145.73,;345.73,-163.93,;349.25,-155.79,)| AuxInfo=1/0/N:19,20,21,11,12,10,13,1,5,2,4,7,6,3,9,14,15,18,8,16,17/E:(1,2,3)(8,9)(10,11)/rA:21nCCCCCCCBrCCCCCCCOOCCCC/rB:d1;s2;d3;s4;s1d5;s6;s7;s3;d9;s10;d11;s12;s9d13;s14;d15;s15;s17;s18;s18;s18;/rC:287,8283,-126,9662,0;287,8062,-138,6670,0;297,7496,-144,4220,0;307,8840,-138,6579,0;307,8292,-126,8966,0;297,7150,-121,1333,0;297,6677,-109,5578,0;305,8179,-101,4207,0;297,7458,-155,9906,0;287,7933,-161,7750,0;287,7846,-173,3329,0;297,7397,-179,0921,0;307,8839,-173,2894,0;307,8436,-161,7505,0;317,7448,-155,9019,0;317,6331,-144,2904,0;327,6918,-161,6938,0;337,6708,-155,7862,0;343,3389,-145,7274,0;345,7339,-163,9291,0;349,2465,-155,7862,0; C18H19BrO2 CDK 04222607282D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 21 22 0 0 0 M V30 BEGIN ATOM M V30 1 C 287.82831 -126.9662 0 0 M V30 2 C 287.80621 -138.66701 0 0 M V30 3 C 297.74963 -144.42204 0 0 M V30 4 C 307.88397 -138.65785 0 0 M V30 5 C 307.82922 -126.89658 0 0 M V30 6 C 297.71503 -121.13332 0 0 M V30 7 C 297.66769 -109.55782 0 0 M V30 8 Br 305.81793 -101.42075 0 0 M V30 9 C 297.74576 -155.99062 0 0 M V30 10 C 287.79333 -161.77498 0 0 M V30 11 C 287.78461 -173.33286 0 0 M V30 12 C 297.73975 -179.09215 0 0 M V30 13 C 307.88391 -173.2894 0 0 M V30 14 C 307.84357 -161.75046 0 0 M V30 15 C 317.74481 -155.90193 0 0 M V30 16 O 317.63306 -144.29044 0 0 M V30 17 O 327.69183 -161.69379 0 0 M V30 18 C 337.67084 -155.78624 0 0 M V30 19 C 343.3389 -145.72742 0 0 M V30 20 C 345.73386 -163.92906 0 0 M V30 21 C 349.24646 -155.78624 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 4 M V30 4 1 4 5 M V30 5 2 5 6 M V30 6 1 6 1 M V30 7 1 6 7 M V30 8 1 7 8 M V30 9 1 3 9 M V30 10 2 9 10 M V30 11 1 10 11 M V30 12 2 11 12 M V30 13 1 12 13 M V30 14 2 13 14 M V30 15 1 14 9 M V30 16 1 14 15 M V30 17 2 15 16 M V30 18 1 15 17 M V30 19 1 17 18 M V30 20 1 18 19 M V30 21 1 18 20 M V30 22 1 18 21 M V30 END BOND M V30 END CTAB M END ZHIPSMIKSRYZFV-UHFFFAOYSA-N InChI=1S/C9H11NO2/c1-6-5-7(9(11)12-2)3-4-8(6)10/h3-5H,10H2,1-2H3 CC1=CC(=CC=C1N)C(=O)OC C1=C(C=CC(=C1C)N)C(=O)OC |(45.09,-41.63,;45.09,-53.14,;55.06,-58.89,;65.02,-53.14,;65.02,-41.63,;55.06,-35.88,;55.06,-24.41,;74.96,-35.9,;35.16,-58.88,;35.16,-70.34,;25.23,-53.14,;15.26,-58.89,)| AuxInfo=1/0/N:9,12,3,4,1,6,2,5,7,8,10,11/rA:12nCCCCCCCNCOOC/rB:d1;s2;d3;s4;s1d5;s2;s5;s6;d7;s7;s11;/rC:45,0902,-41,6320,0;45,0902,-53,1407,0;55,0570,-58,8950,0;65,0238,-53,1407,0;65,0238,-41,6320,0;55,0570,-35,8777,0;35,1580,-58,8750,0;74,9560,-35,8976,0;55,0570,-24,4089,0;35,1580,-70,3437,0;25,2258,-53,1407,0;15,2590,-58,8950,0; C9H11NO2 CDK 04222607282D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 12 12 0 0 0 M V30 BEGIN ATOM M V30 1 C 45.09021 -41.63199 0 0 M V30 2 C 45.09021 -53.14066 0 0 M V30 3 C 55.05701 -58.89499 0 0 M V30 4 C 65.02379 -53.14066 0 0 M V30 5 C 65.02379 -41.63199 0 0 M V30 6 C 55.05701 -35.87766 0 0 M V30 7 C 35.158 -58.875 0 0 M V30 8 N 74.95598 -35.89763 0 0 M V30 9 C 55.05701 -24.40894 0 0 M V30 10 O 35.158 -70.3437 0 0 M V30 11 O 25.22581 -53.14066 0 0 M V30 12 C 15.25903 -58.89499 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 4 M V30 4 1 4 5 M V30 5 2 5 6 M V30 6 1 6 1 M V30 7 1 2 7 M V30 8 1 5 8 M V30 9 1 6 9 M V30 10 2 7 10 M V30 11 1 7 11 M V30 12 1 11 12 M V30 END BOND M V30 END CTAB M END DRCMNHQVZIYACF-UHFFFAOYSA-N InChI=1S/C18H17NO2/c1-18(2)12-21-17(19-18)16-6-4-3-5-15(16)14-9-7-13(11-20)8-10-14/h3-11H,12H2,1-2H3 CC1(C)COC(=N1)C2=C(C=CC=C2)C3=CC=C(C=C3)C=O C1=CC(=CC=C1C=O)C2=CC=CC=C2C=3OCC(N3)(C)C |(149.76,-63.52,;149.74,-75.19,;159.66,-81.01,;169.68,-75.18,;169.63,-63.45,;159.62,-57.78,;164.55,-49.08,;174.48,-54.82,;159.65,-92.54,;149.73,-98.23,;149.72,-109.76,;159.65,-115.58,;169.68,-109.71,;169.64,-98.21,;179.64,-92.45,;190.06,-97.09,;197.69,-88.48,;191.93,-78.57,;180.68,-81.01,;191.82,-67.1,;202.97,-75.54,)| AuxInfo=1/0/N:20,21,11,12,10,13,1,5,2,4,7,17,6,3,9,14,15,18,19,8,16/E:(1,2)(7,8)(9,10)/rA:21nCCCCCCCOCCCCCCCOCCNCC/rB:d1;s2;d3;s4;s1d5;s6;d7;s3;d9;s10;d11;s12;s9d13;s14;s15;s16;s17;d15s18;s18;s18;/rC:149,7649,-63,5195,0;149,7429,-75,1873,0;159,6582,-81,0057,0;169,6844,-75,1782,0;169,6298,-63,4501,0;159,6237,-57,7827,0;164,5512,-49,0847,0;174,4844,-54,8197,0;159,6544,-92,5417,0;149,7300,-98,2301,0;149,7213,-109,7554,0;159,6484,-115,5780,0;169,6844,-109,7121,0;169,6441,-98,2057,0;179,6351,-92,4453,0;190,0571,-97,0878,0;197,6886,-88,4780,0;191,9278,-78,5659,0;180,6763,-81,0098,0;191,8246,-67,1026,0;202,9696,-75,5409,0; C18H17NO2 C(=O)* CHO CDK 04222607282D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 21 23 0 0 0 M V30 BEGIN ATOM M V30 1 C 149.76491 -63.51952 0 0 M V30 2 C 149.74287 -75.18733 0 0 M V30 3 C 159.6582 -81.00574 0 0 M V30 4 C 169.6844 -75.17819 0 0 M V30 5 C 169.62982 -63.45006 0 0 M V30 6 C 159.62373 -57.7827 0 0 M V30 7 C 164.55116 -49.08469 0 0 M V30 8 O 174.48442 -54.81966 0 0 M V30 9 C 159.65437 -92.5417 0 0 M V30 10 C 149.73004 -98.23013 0 0 M V30 11 C 149.72133 -109.75543 0 0 M V30 12 C 159.64839 -115.57805 0 0 M V30 13 C 169.68436 -109.71205 0 0 M V30 14 C 169.64412 -98.20567 0 0 M V30 15 C 179.63509 -92.44534 0 0 M V30 16 O 190.05714 -97.08784 0 0 M V30 17 C 197.68861 -88.478 0 0 M V30 18 C 191.92783 -78.56595 0 0 M V30 19 N 180.6763 -81.0098 0 0 M V30 20 C 191.82463 -67.10255 0 0 M V30 21 C 202.96956 -75.54086 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 4 M V30 4 1 4 5 M V30 5 2 5 6 M V30 6 1 6 1 M V30 7 2 7 8 M V30 8 1 6 7 M V30 9 1 3 9 M V30 10 2 9 10 M V30 11 1 10 11 M V30 12 2 11 12 M V30 13 1 12 13 M V30 14 2 13 14 M V30 15 1 14 9 M V30 16 1 14 15 M V30 17 1 15 16 M V30 18 1 16 17 M V30 19 1 17 18 M V30 20 1 18 19 M V30 21 2 19 15 M V30 22 1 18 20 M V30 23 1 18 21 M V30 END BOND M V30 END CTAB M END VXWBQOJISHAKKM-UHFFFAOYSA-N InChI=1S/C7H7BO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5,10-11H C1=C(C=CC(=C1)B(O)O)C=O C1=CC(=CC=C1C=O)B(O)O |(10.78,-78.33,;10.78,-89.84,;20.75,-95.6,;30.72,-89.84,;30.72,-78.33,;20.75,-72.58,;25.72,-63.98,;35.65,-69.71,;20.75,-107.06,;30.68,-112.8,;10.82,-112.8,)| AuxInfo=1/0/N:1,5,2,4,7,6,3,9,8,10,11/E:(1,2)(3,4)(10,11)/rA:11nCCCCCCCOBOO/rB:d1;s2;d3;s4;s1d5;s6;d7;s3;s9;s9;/rC:10,7823,-78,3321,0;10,7823,-89,8407,0;20,7491,-95,5950,0;30,7159,-89,8407,0;30,7159,-78,3321,0;20,7491,-72,5777,0;25,7157,-63,9753,0;35,6490,-69,7103,0;20,7491,-107,0649,0;30,6824,-112,7999,0;10,8159,-112,7999,0; C7H7BO3 C(=O)* CHO CDK 04222607282D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 11 11 0 0 0 M V30 BEGIN ATOM M V30 1 C 10.78233 -78.33206 0 0 M V30 2 C 10.78233 -89.8407 0 0 M V30 3 C 20.74911 -95.59502 0 0 M V30 4 C 30.7159 -89.8407 0 0 M V30 5 C 30.7159 -78.33206 0 0 M V30 6 C 20.74911 -72.57774 0 0 M V30 7 C 25.71573 -63.97528 0 0 M V30 8 O 35.64899 -69.71025 0 0 M V30 9 B 20.74911 -107.06494 0 0 M V30 10 O 30.68236 -112.79991 0 0 M V30 11 O 10.81586 -112.79991 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 4 M V30 4 1 4 5 M V30 5 2 5 6 M V30 6 1 6 1 M V30 7 2 7 8 M V30 8 1 6 7 M V30 9 1 3 9 M V30 10 1 9 10 M V30 11 1 9 11 M V30 END BOND M V30 END CTAB M END XLCYXINIUJNTPF-UHFFFAOYSA-N InChI=1S/C11H12BrNO/c1-11(2)7-14-10(13-11)8-5-3-4-6-9(8)12/h3-6H,7H2,1-2H3 CC1(C)COC(=N1)C2=C(C=CC=C2)Br C1=CC=CC(=C1Br)C=2OCC(N2)(C)C |(57.22,-78.34,;57.18,-89.97,;67.13,-95.8,;77.2,-89.97,;77.16,-78.26,;67.13,-72.59,;67.05,-61,;87.19,-72.46,;97.78,-77.18,;105.49,-68.59,;99.7,-58.56,;88.39,-61,;99.62,-47.01,;109.61,-52.68,)| AuxInfo=1/0/N:13,14,3,2,4,1,10,5,6,8,11,7,12,9/E:(1,2)/rA:14nCCCCCCBrCOCCNCC/rB:d1;s2;d3;s4;s1d5;s6;s5;s8;s9;s10;d8s11;s11;s11;/rC:57,2183,-78,3394,0;57,1777,-89,9698,0;67,1284,-95,8022,0;77,2008,-89,9698,0;77,1602,-78,2582,0;67,1284,-72,5851,0;67,0472,-60,9952,0;87,1920,-72,4633,0;97,7827,-77,1810,0;105,4947,-68,5886,0;99,6998,-58,5567,0;88,3910,-60,9952,0;99,6186,-47,0075,0;109,6098,-52,6807,0; C11H12BrNO CDK 04222607282D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 14 15 0 0 0 M V30 BEGIN ATOM M V30 1 C 57.21834 -78.33939 0 0 M V30 2 C 57.17775 -89.9698 0 0 M V30 3 C 67.12839 -95.80217 0 0 M V30 4 C 77.20079 -89.9698 0 0 M V30 5 C 77.16019 -78.25821 0 0 M V30 6 C 67.12839 -72.58507 0 0 M V30 7 Br 67.04721 -60.99524 0 0 M V30 8 C 87.19202 -72.46329 0 0 M V30 9 O 97.78273 -77.18103 0 0 M V30 10 C 105.49471 -68.58858 0 0 M V30 11 C 99.69978 -58.55675 0 0 M V30 12 N 88.39098 -60.99524 0 0 M V30 13 C 99.61861 -47.00752 0 0 M V30 14 C 109.60982 -52.68066 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 4 M V30 4 1 4 5 M V30 5 2 5 6 M V30 6 1 1 6 M V30 7 1 6 7 M V30 8 1 5 8 M V30 9 1 8 9 M V30 10 1 9 10 M V30 11 1 10 11 M V30 12 1 11 12 M V30 13 2 8 12 M V30 14 1 11 13 M V30 15 1 11 14 M V30 END BOND M V30 END CTAB M END HLOKZJWEQPVFFJ-UHFFFAOYSA-N InChI=1S/C19H22N4O/c1-4-7-17(24)22-18-12(2)10-13(11-14(18)20)19-21-15-8-5-6-9-16(15)23(19)3/h5-6,8-11H,4,7,20H2,1-3H3,(H,22,24) CCCC(=O)NC1=C(C=C(C=C1C)C2=NC3=CC=CC=C3N2C)N C1=CC=C2C(=C1)N=C(N2C)C3=CC(=C(C(=C3)C)NC(CCC)=O)N |(27.49,-99.92,;27.47,-111.59,;37.53,-117.37,;47.58,-111.57,;47.57,-99.85,;37.5,-94.15,;58.67,-96.28,;65.57,-105.75,;58.68,-115.14,;58.53,-126.69,;77.05,-105.7,;82.87,-115.71,;94.33,-115.66,;100.2,-105.64,;94.25,-95.62,;82.74,-95.73,;100.01,-85.51,;111.42,-108.1,;119.21,-99.56,;130.49,-102.03,;138.28,-93.49,;149.56,-95.96,;115.71,-88.55,;102.05,-124.23,)| AuxInfo=1/1/N:24,19,10,23,1,2,21,4,3,14,12,13,11,17,8,9,20,16,6,18,7,15,5,22/rA:24nCCCCNCNCCCCCCCNCCNCCCOCC/rB:d1;s2;s1;;s5;d6;d4s7;d3s5s8;s5;s6;d11;;s11d13;;s13s15;s12d16;s17;s13;s15;s20;d20;s21;s23;/rC:27,4950,-99,9248,0;27,4728,-111,5898,0;37,5340,-117,3666,0;37,4993,-94,1501,0;58,6765,-115,1390,0;65,5732,-105,7455,0;58,6674,-96,2781,0;47,5716,-99,8550,0;47,5767,-111,5741,0;58,5344,-126,6903,0;77,0454,-105,6952,0;82,8694,-115,7113,0;94,2509,-95,6192,0;82,7396,-95,7300,0;111,4246,-108,0951,0;100,1957,-105,6358,0;94,3316,-115,6572,0;102,0517,-124,2307,0;100,0083,-85,5116,0;119,2079,-99,5575,0;130,4934,-102,0293,0;115,7058,-88,5481,0;138,2768,-93,4917,0;149,5622,-95,9634,0; C19H22N4O CDK 04222607282D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 24 26 0 0 0 M V30 BEGIN ATOM M V30 1 C 27.49498 -99.92484 0 0 M V30 2 C 27.47279 -111.58981 0 0 M V30 3 C 37.53397 -117.36662 0 0 M V30 4 C 37.49925 -94.15005 0 0 M V30 5 N 58.67647 -115.13898 0 0 M V30 6 C 65.57315 -105.74545 0 0 M V30 7 N 58.66739 -96.27808 0 0 M V30 8 C 47.57161 -99.85497 0 0 M V30 9 C 47.57668 -111.57405 0 0 M V30 10 C 58.53441 -126.69034 0 0 M V30 11 C 77.04536 -105.69524 0 0 M V30 12 C 82.86945 -115.71129 0 0 M V30 13 C 94.2509 -95.61919 0 0 M V30 14 C 82.73956 -95.73004 0 0 M V30 15 N 111.42456 -108.09514 0 0 M V30 16 C 100.19566 -105.63576 0 0 M V30 17 C 94.33162 -115.65721 0 0 M V30 18 N 102.05173 -124.23065 0 0 M V30 19 C 100.00835 -85.51161 0 0 M V30 20 C 119.20793 -99.55751 0 0 M V30 21 C 130.49341 -102.02928 0 0 M V30 22 O 115.7058 -88.5481 0 0 M V30 23 C 138.27676 -93.49167 0 0 M V30 24 C 149.56224 -95.96342 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 9 M V30 4 2 8 4 M V30 5 1 4 1 M V30 6 1 8 9 M V30 7 2 6 7 M V30 8 1 5 6 M V30 9 1 7 8 M V30 10 1 9 5 M V30 11 1 5 10 M V30 12 1 6 11 M V30 13 2 11 12 M V30 14 1 12 17 M V30 15 1 16 13 M V30 16 2 13 14 M V30 17 1 14 11 M V30 18 2 16 17 M V30 19 1 15 16 M V30 20 1 17 18 M V30 21 1 13 19 M V30 22 1 15 20 M V30 23 1 20 21 M V30 24 2 20 22 M V30 25 1 21 23 M V30 26 1 23 24 M V30 END BOND M V30 END CTAB M END KCGLCZNSSVOXKO-UHFFFAOYSA-N InChI=1S/C37H37N5O/c1-6-11-33-39-34-24(2)20-27(35-38-30-14-9-10-15-31(30)41(35)5)21-32(34)42(33)22-25-16-18-26(19-17-25)28-12-7-8-13-29(28)36-40-37(3,4)23-43-36/h7-10,12-21H,6,11,22-23H2,1-5H3 CCCC1=NC2=C(C=C(C=C2C)C3=NC4=C(C=CC=C4)N3C)N1CC5=CC=C(C=C5)C6=C(C=CC=C6)C7=NC(C)(C)CO7 C1=CC=C2C(=C1)N=C(N2C)C3=CC4=C(C(=C3)C)N=C(CCC)N4CC5=CC=C(C=C5)C6=CC=CC=C6C7=NC(CO7)(C)C |(87.57,-207.67,;87.55,-219.39,;97.67,-225.23,;107.77,-219.37,;107.76,-207.6,;97.63,-201.91,;118.91,-204.04,;125.88,-213.56,;118.92,-223.01,;118.78,-234.61,;137.4,-213.51,;143.21,-223.58,;154.73,-223.53,;160.65,-213.45,;154.64,-203.38,;143.08,-203.49,;160.47,-193.22,;171.94,-215.9,;173.18,-227.38,;183.29,-233.29,;183.31,-244.88,;193.42,-250.7,;162.51,-232.08,;160.11,-243.38,;150.09,-249.16,;140.08,-243.38,;130.07,-249.16,;130.07,-260.73,;140.08,-266.51,;150.09,-260.73,;120.06,-266.51,;110.02,-260.71,;99.98,-266.51,;99.98,-278.1,;110.02,-283.89,;120.06,-278.1,;130.06,-283.87,;131.27,-295.4,;142.61,-297.81,;148.41,-287.77,;140.65,-279.16,;147.31,-308.37,;154.15,-298.42,)| AuxInfo=1/0/N:23,20,42,43,10,22,33,34,1,2,21,32,35,4,3,26,30,27,29,14,12,24,40,13,25,28,11,31,36,8,9,17,19,16,6,37,39,7,15,38,5,18,41/E:(3,4)(16,17)(18,19)/rA:43nCCCCNCNCCCCCCCNCCNCCCCCCCCCCCCCCCCCCCNCCOCC/rB:d1;s2;s1;;s5;d6;d4s7;d3s5s8;s5;s6;d11;;s11d13;;s13s15;s12d16;s17;d15s18;s13;s19;s21;s22;s18;s24;d25;s26;d27;s28;s25d29;s28;d31;s32;d33;s34;s31d35;s36;d37;s38;s39;s37s40;s39;s39;/rC:87,5748,-207,6728,0;87,5526,-219,3888,0;97,6688,-225,2312,0;97,6341,-201,9123,0;118,9188,-223,0091,0;125,8783,-213,5589,0;118,9097,-204,0350,0;107,7615,-207,6031,0;107,7665,-219,3730,0;118,7771,-234,6118,0;137,4020,-213,5088,0;143,2117,-223,5800,0;154,6449,-203,3778,0;143,0821,-203,4884,0;171,9359,-215,9028,0;160,6548,-213,4494,0;154,7255,-223,5260,0;162,5063,-232,0782,0;173,1786,-227,3843,0;160,4680,-193,2153,0;183,2946,-233,2889,0;183,3069,-244,8795,0;193,4227,-250,7042,0;160,1073,-243,3826,0;150,0932,-249,1643,0;140,0791,-243,3826,0;130,0650,-249,1643,0;130,0650,-260,7275,0;140,0791,-266,5092,0;150,0932,-260,7275,0;120,0571,-266,5056,0;110,0181,-260,7097,0;99,9791,-266,5056,0;99,9791,-278,0977,0;110,0181,-283,8936,0;120,0571,-278,0977,0;130,0612,-283,8735,0;131,2729,-295,4020,0;142,6116,-297,8121,0;148,4075,-287,7731,0;140,6510,-279,1586,0;147,3101,-308,3652,0;154,1475,-298,4167,0; C37H37N5O CDK 04222607282D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 43 49 0 0 0 M V30 BEGIN ATOM M V30 1 C 87.57477 -207.67276 0 0 M V30 2 C 87.5526 -219.38878 0 0 M V30 3 C 97.66879 -225.23122 0 0 M V30 4 C 97.63414 -201.91229 0 0 M V30 5 N 118.91879 -223.00912 0 0 M V30 6 C 125.87833 -213.55891 0 0 M V30 7 N 118.90973 -204.03502 0 0 M V30 8 C 107.76152 -207.60306 0 0 M V30 9 C 107.76654 -219.37303 0 0 M V30 10 C 118.7771 -234.61177 0 0 M V30 11 C 137.40204 -213.50879 0 0 M V30 12 C 143.21173 -223.57999 0 0 M V30 13 C 154.6449 -203.37778 0 0 M V30 14 C 143.08212 -203.48837 0 0 M V30 15 N 171.93587 -215.90277 0 0 M V30 16 C 160.65485 -213.44945 0 0 M V30 17 C 154.72546 -223.52602 0 0 M V30 18 N 162.50632 -232.07822 0 0 M V30 19 C 173.17865 -227.38432 0 0 M V30 20 C 160.46805 -193.21532 0 0 M V30 21 C 183.29456 -233.28891 0 0 M V30 22 C 183.30685 -244.8795 0 0 M V30 23 C 193.42267 -250.70418 0 0 M V30 24 C 160.10728 -243.38264 0 0 M V30 25 C 150.09319 -249.16428 0 0 M V30 26 C 140.0791 -243.38264 0 0 M V30 27 C 130.065 -249.16428 0 0 M V30 28 C 130.065 -260.72754 0 0 M V30 29 C 140.0791 -266.50919 0 0 M V30 30 C 150.09319 -260.72754 0 0 M V30 31 C 120.05707 -266.50565 0 0 M V30 32 C 110.0181 -260.70966 0 0 M V30 33 C 99.97914 -266.50565 0 0 M V30 34 C 99.97914 -278.09766 0 0 M V30 35 C 110.0181 -283.89362 0 0 M V30 36 C 120.05707 -278.09766 0 0 M V30 37 C 130.06117 -283.8735 0 0 M V30 38 N 131.27287 -295.40198 0 0 M V30 39 C 142.61156 -297.8121 0 0 M V30 40 C 148.40755 -287.77313 0 0 M V30 41 O 140.65099 -279.15863 0 0 M V30 42 C 147.31009 -308.36517 0 0 M V30 43 C 154.14749 -298.41669 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 9 M V30 4 2 8 4 M V30 5 1 4 1 M V30 6 1 8 9 M V30 7 2 6 7 M V30 8 1 5 6 M V30 9 1 7 8 M V30 10 1 9 5 M V30 11 1 5 10 M V30 12 1 6 11 M V30 13 2 11 12 M V30 14 1 12 17 M V30 15 1 16 13 M V30 16 2 13 14 M V30 17 1 14 11 M V30 18 2 16 17 M V30 19 1 15 16 M V30 20 1 17 18 M V30 21 2 19 15 M V30 22 1 13 20 M V30 23 1 19 21 M V30 24 1 21 22 M V30 25 1 22 23 M V30 26 1 18 19 M V30 27 1 18 24 M V30 28 1 24 25 M V30 29 2 25 26 M V30 30 1 26 27 M V30 31 2 27 28 M V30 32 1 28 29 M V30 33 2 29 30 M V30 34 1 30 25 M V30 35 1 28 31 M V30 36 2 31 32 M V30 37 1 32 33 M V30 38 2 33 34 M V30 39 1 34 35 M V30 40 2 35 36 M V30 41 1 36 31 M V30 42 1 36 37 M V30 43 2 37 38 M V30 44 1 38 39 M V30 45 1 39 40 M V30 46 1 40 41 M V30 47 1 41 37 M V30 48 1 39 42 M V30 49 1 39 43 M V30 END BOND M V30 END CTAB M END KJLBCXGNOGWOBT-UHFFFAOYSA-N InChI=1S/C37H39N5O2/c1-6-11-33(43)40-34-24(2)20-27(35-39-30-14-9-10-15-32(30)42(35)5)21-31(34)38-22-25-16-18-26(19-17-25)28-12-7-8-13-29(28)36-41-37(3,4)23-44-36/h7-10,12-21,38H,6,11,22-23H2,1-5H3,(H,40,43) CCCC(=O)NC1=C(C=C(C=C1C)C2=NC3=CC=CC=C3N2C)NCC4=CC=C(C=C4)C5=C(C=CC=C5)C6=NC(C)(C)CO6 C1=CC=C2C(=C1)N=C(N2C)C3=CC(=C(C(=C3)C)NC(CCC)=O)NCC4=CC=C(C=C4)C5=CC=CC=C5C6=NC(CO6)(C)C |(277.08,-68.85,;277.06,-80.6,;287.2,-86.46,;297.32,-80.58,;297.32,-68.78,;287.17,-63.08,;308.49,-65.21,;315.48,-74.76,;308.5,-84.23,;308.36,-95.86,;327.03,-74.7,;332.86,-84.8,;344.4,-84.75,;350.34,-74.65,;344.32,-64.55,;332.73,-64.66,;350.16,-54.36,;361.65,-77.1,;369.42,-68.56,;380.71,-71.01,;388.48,-62.46,;399.77,-64.92,;365.9,-57.55,;352.2,-93.32,;352.2,-104.91,;342.16,-110.71,;332.12,-104.91,;322.08,-110.71,;322.08,-122.3,;332.12,-128.1,;342.16,-122.3,;312.08,-128.08,;302.04,-122.28,;292,-128.08,;292,-139.67,;302.04,-145.46,;312.08,-139.67,;322.08,-145.44,;323.29,-156.97,;334.63,-159.38,;340.43,-149.34,;332.67,-140.73,;339.33,-169.94,;346.17,-159.99,)| AuxInfo=1/1/N:24,19,43,44,10,23,34,35,1,2,21,33,36,4,3,27,31,28,30,14,12,25,41,13,26,29,11,32,37,8,17,9,20,16,6,38,40,18,7,15,39,5,22,42/E:(3,4)(16,17)(18,19)/rA:44nCCCCNCNCCCCCCCNCCNCCCOCCCCCCCCCCCCCCCCNCCOCC/rB:d1;s2;s1;;s5;d6;d4s7;d3s5s8;s5;s6;d11;;s11d13;;s13s15;s12d16;s17;s13;s15;s20;d20;s21;s23;s18;s25;d26;s27;d28;s29;s26d30;s29;d32;s33;d34;s35;s32d36;s37;d38;s39;s40;s38s41;s40;s40;/rC:277,0815,-68,8544,0;277,0593,-80,5995,0;287,2006,-86,4565,0;287,1659,-63,0796,0;308,5034,-84,2289,0;315,4802,-74,7552,0;308,4943,-65,2076,0;297,3184,-68,7845,0;297,3234,-80,5838,0;308,3613,-95,8603,0;327,0325,-74,7049,0;332,8566,-84,8011,0;344,3182,-64,5488,0;332,7267,-64,6596,0;361,6521,-77,1049,0;350,3431,-74,6455,0;344,3989,-84,7471,0;352,1992,-93,3205,0;350,1558,-54,3611,0;369,4229,-68,5557,0;380,7119,-71,0108,0;365,9044,-57,5515,0;388,4827,-62,4617,0;399,7718,-64,9167,0;352,1992,-104,9125,0;342,1602,-110,7085,0;332,1212,-104,9125,0;322,0823,-110,7085,0;322,0823,-122,3005,0;332,1212,-128,0965,0;342,1602,-122,3005,0;312,0782,-128,0763,0;302,0392,-122,2803,0;292,0002,-128,0763,0;292,0002,-139,6683,0;302,0392,-145,4643,0;312,0782,-139,6683,0;322,0823,-145,4442,0;323,2939,-156,9727,0;334,6326,-159,3828,0;340,4286,-149,3439,0;332,6721,-140,7293,0;339,3312,-169,9359,0;346,1686,-159,9874,0; C37H39N5O2 CDK 04222607282D 0 0 0 0 0 999 V3000 M V30 BEGIN CTAB M V30 COUNTS 44 49 0 0 0 M V30 BEGIN ATOM M V30 1 C 277.08148 -68.85443 0 0 M V30 2 C 277.05927 -80.59953 0 0 M V30 3 C 287.20059 -86.45648 0 0 M V30 4 C 287.16586 -63.07964 0 0 M V30 5 N 308.50336 -84.22887 0 0 M V30 6 C 315.48016 -74.75519 0 0 M V30 7 N 308.49426 -65.20764 0 0 M V30 8 C 297.31836 -68.78455 0 0 M V30 9 C 297.32343 -80.58377 0 0 M V30 10 C 308.3613 -95.86034 0 0 M V30 11 C 327.03253 -74.70493 0 0 M V30 12 C 332.8566 -84.80115 0 0 M V30 13 C 344.31818 -64.54877 0 0 M V30 14 C 332.72672 -64.65964 0 0 M V30 15 N 361.6521 -77.10486 0 0 M V30 16 C 350.34308 -74.64546 0 0 M V30 17 C 344.39893 -84.74707 0 0 M V30 18 N 352.19916 -93.32048 0 0 M V30 19 C 350.15579 -54.36105 0 0 M V30 20 C 369.42285 -68.55574 0 0 M V30 21 C 380.71194 -71.01082 0 0 M V30 22 O 365.90442 -57.55153 0 0 M V30 23 C 388.48267 -62.46169 0 0 M V30 24 C 399.77182 -64.91675 0 0 M V30 25 C 352.19916 -104.91248 0 0 M V30 26 C 342.16019 -110.70848 0 0 M V30 27 C 332.12122 -104.91248 0 0 M V30 28 C 322.08228 -110.70848 0 0 M V30 29 C 322.08228 -122.30048 0 0 M V30 30 C 332.12122 -128.09647 0 0 M V30 31 C 342.16019 -122.30048 0 0 M V30 32 C 312.07816 -128.07634 0 0 M V30 33 C 302.03918 -122.28035 0 0 M V30 34 C 292.00024 -128.07634 0 0 M V30 35 C 292.00024 -139.66833 0 0 M V30 36 C 302.03918 -145.46434 0 0 M V30 37 C 312.07816 -139.66833 0 0 M V30 38 C 322.08228 -145.44421 0 0 M V30 39 N 323.29395 -156.9727 0 0 M V30 40 C 334.63263 -159.38283 0 0 M V30 41 C 340.42865 -149.34386 0 0 M V30 42 O 332.67209 -140.72932 0 0 M V30 43 C 339.33118 -169.93587 0 0 M V30 44 C 346.16858 -159.9874 0 0 M V30 END ATOM M V30 BEGIN BOND M V30 1 2 1 2 M V30 2 1 2 3 M V30 3 2 3 9 M V30 4 2 8 4 M V30 5 1 4 1 M V30 6 1 8 9 M V30 7 2 6 7 M V30 8 1 5 6 M V30 9 1 7 8 M V30 10 1 9 5 M V30 11 1 5 10 M V30 12 1 6 11 M V30 13 2 11 12 M V30 14 1 12 17 M V30 15 1 16 13 M V30 16 2 13 14 M V30 17 1 14 11 M V30 18 2 16 17 M V30 19 1 15 16 M V30 20 1 17 18 M V30 21 1 13 19 M V30 22 1 15 20 M V30 23 1 20 21 M V30 24 2 20 22 M V30 25 1 21 23 M V30 26 1 23 24 M V30 27 1 18 25 M V30 28 1 25 26 M V30 29 2 26 27 M V30 30 1 27 28 M V30 31 2 28 29 M V30 32 1 29 30 M V30 33 2 30 31 M V30 34 1 31 26 M V30 35 1 29 32 M V30 36 2 32 33 M V30 37 1 33 34 M V30 38 2 34 35 M V30 39 1 35 36 M V30 40 2 36 37 M V30 41 1 37 32 M V30 42 1 37 38 M V30 43 2 38 39 M V30 44 1 39 40 M V30 45 1 40 41 M V30 46 1 41 42 M V30 47 1 42 38 M V30 48 1 40 43 M V30 49 1 40 44 M V30 END BOND M V30 END CTAB M END We are grateful to SVNIT, Surat and IICT, Hyderabad for supporting this work. Drugs U.S. Patent J. Med. Chem. J. Med. Chem. Org. Process Res. Dev. J. Med. Chem. Ger. Pat. Appl. J. Organomet. Chem. Tetrahedron Lett. Int. Pat. Appl. Tetrahedron J. Org. Chem. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)