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Beilstein J. Org. Chem. 2014, 10, 316–322, doi:10.3762/bjoc.10.29
Graphical Abstract
Figure 1: Structures of the strongly cytotoxic marine natural products malevamide D (1), isodolastatin H (2),...
Scheme 1: Total synthesis of malevamide D (1). a) DMSO (16 equiv), NEt3 (5 equiv), pyridine·SO3 (5 equiv), 0 ...
Scheme 2: Formation of oxazolylphosphate 18 on attempted DEPC-mediated coupling of dipeptide 15.
Scheme 3: Synthesis of tosyloximes (Z)-22 and (E)-22, X-ray structure of (E)-22. a) NH2OH·HCl (1.5 equiv), py...
Scheme 4: Synthesis of photo malevamide D 30. a) NH3(l), t-BuOMe, −40 °C, 2 h, rt, 16 h, quant. b) I2 (1.2 eq...
Figure 2: DSC curve of diazirine 25, heating rate 5 °C/min.
Beilstein J. Org. Chem. 2013, 9, 2202–2215, doi:10.3762/bjoc.9.259
Figure 1: Natural products having a 1,2,4-oxadiazole core.
Figure 2: Examples of 1,2,4-oxadiazole antitumorals.
Scheme 1: Common synthetic strategies toward 1,2,4-oxadiazoles; (a) amidoxime route; (b) 1,3 dipolar cycloadd...
Scheme 2: One-pot synthesis of 4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)aniline (1) by using the amidoxime route....
Figure 3: Molecular structure of 4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)aniline (1). Atoms are drawn as 50% the...
Figure 4: Packing diagram of compound 1. Hydrogen bonds are indicated as dashed lines.
Scheme 3: One-pot synthesis of 4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)aniline (1) by using the 1,3-dipolar cycl...
Figure 5: Molecular structure of 3-tert-butyl-5-(4-nitrophenyl)-1,2,4-oxadiazole (2). Atoms are drawn as 50% ...
Figure 6: Packing diagram of compound (2) showing C–H···O interactions.
Scheme 4: Synthesis of 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)pyrrolidine-2,5-dione (4).
Figure 7: Molecular structure of 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)pyrrolidine-2,5-dione (4). At...
Figure 8: Molecular structure of 4-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenylamino)-4 oxobutanoate (5). Ato...
Figure 9: Packing diagram of compound (5). Dashed lines indicate hydrogen bonds.
Scheme 5: Synthesis of 1-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenyl)-1H-pyrrole-2,5-dione (7).
Figure 10: Molecular structure of (Z)-4-(4-(3-tert-butyl-1,2,4-oxadiazol-5-yl)phenylamino)-4-oxobut-2-enoic ac...
Figure 11: Packing diagram of compound 6. Dashed lines indicate hydrogen bonds.
Figure 12: In vitro antitumor activity of compounds 1, 3–7 toward 11 human tumor cell lines.
Figure 13: Individual IC50 values [µM] of compounds 1, 3–7 in a panel of 11 human tumor cell lines.