Synthesis of ether lipids: natural compounds and analogues

• Marco Antônio G. B. Gomes,
• Alicia Bauduin,
• Chloé Le Roux,
• Romain Fouinneteau,
• Wilfried Berthe,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

Unravelling a trichloroacetic acid-catalyzed cascade access to benzo[f]chromeno[2,3-h]quinoxalinoporphyrins

• Chandra Sekhar Tekuri,
• Pargat Singh and
• Mahendra Nath

Beilstein J. Org. Chem. 2023, 19, 1216–1224, doi:10.3762/bjoc.19.89

• -tetraarylporphyrins 1 were synthesized from the corresponding 2-nitro-meso-tetraarylporphyrins in two steps by following the literature procedure [42]. The first step involved an amination of copper(II) 2-nitro-meso-tetraarylporphyrins by using 4-amino-4H-1,2,4-triazole in the presence of NaOH in refluxing ethanol

Synthesis of imidazo[1,2-a]pyridine-containing peptidomimetics by tandem of Groebke–Blackburn–Bienaymé and Ugi reactions

• Oleksandr V. Kolomiiets,
• Alexander V. Tsygankov,
• Maryna N. Kornet,
• Aleksander A. Brazhko,
• Vladimir I. Musatov and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2023, 19, 727–735, doi:10.3762/bjoc.19.53

• target compounds, which contained two pharmacophores – [1,2-a]pyridine (1H-imidazo[1,2-b][1,2,4]triazole) and peptidomimetic moieties – were evaluated for their antibacterial activity and exhibited a weak effect. Drugs possessing imidazo[1,2-a]pyridine unit. Drugs possessing peptide unit. Diversity of

pH-Responsive fluorescent supramolecular nanoparticles based on tetraphenylethylene-labelled chitosan and a six-fold carboxylated tribenzotriquinacene

• Nan Yang,
• Yi-Yan Zhu,
• Wei-Xiu Lin,
• Yi-Long Lu and
• Wen-Rong Xu

Beilstein J. Org. Chem. 2023, 19, 635–645, doi:10.3762/bjoc.19.45

• -methyltribenzotriquinacene-2,3,6,7,10,11-hexayl)hexakis(oxy))hexaacetate (TBTQ-C6) and 2,2',2'',2''',2'''',2'''''-((((12d-methyltribenzotriquinacene-2,3,6,7,10,11-hexayl)hexakis(oxy))hexakis(methylene))hexakis(1H-1,2,3-triazole-4,1-diyl))hexaacetate (TBTQ-CB6), which act as host molecules to bind to guest molecules to

Phenanthridine–pyrene conjugates as fluorescent probes for DNA/RNA and an inactive mutant of dipeptidyl peptidase enzyme

• Josipa Matić,
• Tana Tandarić,
• Marijana Radić Stojković,
• Filip Šupljika,
• Zrinka Karačić,
• Ana Tomašić Paić,
• Lucija Horvat,
• Robert Vianello and
• Lidija-Marija Tumir

Beilstein J. Org. Chem. 2023, 19, 550–565, doi:10.3762/bjoc.19.40

• fluorescence response. Compounds that consisted of pyrrole-guanidine attached to larger aryl moieties (pyrene and phenanthridine) bind to the human DPP III enzyme [17]. Pyrene–cyanine conjugates connected with a rigid triazole-peptide linker were designed and synthesized in our group and showed a strong pyrene

CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview

• Dileep Kumar Singh

Beilstein J. Org. Chem. 2023, 19, 349–379, doi:10.3762/bjoc.19.29

• connect two diverse moieties in a single framework. Therefore, this review focuses on the synthesis and photophysical studies of β- and meso-substituted and 1,2,3-triazole-fused porphyrin conjugates. All of the porphyrin conjugates discussed here are synthesized via a copper(I)-catalyzed Huisgen 1,3

• -dipolar cycloaddition reaction between an azide and a terminal alkyne, also popular as "click reaction" or CuAAC reaction. Moreover, the 1,2,3-triazole ring also serves as a spacer and an electron transfer bridge between the porphyrin and the attached chromophores. In order to provide a critical overview

• of the synthesis and properties of various porphyrin-triazole hybrids, this review will discuss some of the key reactions involved in the preparation of triazole-linked porphyrin conjugates. Keywords: azide–alkyne; click chemistry; CuAAC; 1,3-dipolar cycloaddition; porphyrin; 1,2,3-triazole

Synthesis and characterisation of new antimalarial fluorinated triazolopyrazine compounds

• Kah Yean Lum,
• Jonathan M. White,
• Daniel J. G. Johnson,
• Vicky M. Avery and
• Rohan A. Davis

Beilstein J. Org. Chem. 2023, 19, 107–114, doi:10.3762/bjoc.19.11

• , cyano, nitro, or halogenated groups at the para-position were crucial for activity [5][16][20]. Thus, compounds 1–3 with a para-phenyl-OCHF2, -Cl or -CN substituent at the C3 position of the triazole were selected as scaffolds in this study. In addition, the reported SAR data also indicated that the use

A novel bis-triazole scaffold accessed via two tandem [3 + 2] cycloaddition events including an uncatalyzed, room temperature azide–alkyne click reaction

• Ksenia Malkova,
• Andrey Bubyrev,
• Vasilisa Krivovicheva,
• Dmitry Dar’in,
• Alexander Bunev and
• Mikhail Krasavin

Beilstein J. Org. Chem. 2022, 18, 1636–1641, doi:10.3762/bjoc.18.175

• University, Kaliningrad 236016, Russian Federation 10.3762/bjoc.18.175 Abstract The previously described α-acetyl-α-diazomethanesulfonamide was employed in a three-component reaction with azide-containing benzaldehydes and propargylamines. Besides the initial formation of the triazole core, the reaction

• ; Introduction 1,2,3-Triazoles are well-established heterocycles in drug discovery [1] and are even considered pharmacophores (i.e., structural motifs defining the compound’s biological activity profile) on their own [2]. Therefore, synthetic methods allowing to construct a 1,2,3-triazole heterocycle are a

• molecular scaffold. Pondering various opportunities for post-condensational modifications of the 1,5-disubstituted 1,2,3-triazole core according to this strategy, we turned our attention to such powerful transformation as the azide–alkyne [3 + 2] cycloaddition (also known as the azide–alkyne click reaction

Preparation of β-cyclodextrin-based dimers with selectively methylated rims and their use for solubilization of tetracene

• Konstantin Lebedinskiy,
• Volodymyr Lobaz and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2022, 18, 1596–1606, doi:10.3762/bjoc.18.170

• triazole ring in 10 are at 2.6–3.0 ppm; the 5A-hydrogen is also quite distinctive on the spectra (4.17–4.23 ppm). These observations agree with the reported data [13][32] and may help to confirm the structure. The other resonance signals from the CD skeleton are difficult to follow due to total overlapping

• to the carbon-3 positions. The other signals (36H) from Me–O–C3 are concentrated in two overlapped singlets of different intensities. The single peak at 3.54 ppm represents all signals from Me–O–C2, implying that the triazole ring interacts mainly with the hydrogens inside the cavity. Another solid

• proof of the partial self-inclusion of the triazole into the internal space of CD is the fragment of the NOESY spectrum (Figure 1a), where the interaction of the triazole hydrogen with H–C6A, H–C5A, and H–C6 from the glucose unit next to the unit A is clearly seen indicating the interaction between the

New triazole-substituted triterpene derivatives exhibiting anti-RSV activity: synthesis, biological evaluation, and molecular modeling

• Elenilson F. da Silva,
• Krist Helen Antunes Fernandes,
• Denise Diedrich,
• Jessica Gotardi,
• Marcia Silvana Freire Franco,
• Carlos Henrique Tomich de Paula da Silva,
• Ana Paula Duarte de Souza and
• Simone Cristina Baggio Gnoatto

Beilstein J. Org. Chem. 2022, 18, 1524–1531, doi:10.3762/bjoc.18.161

• , University of São Paulo, Ribeirão Preto, SP 14040-020, Brazil 10.3762/bjoc.18.161 Abstract Respiratory syncytial virus (RSV) is a major cause of acute lower respiratory tract infections in infants. Currently, ribavirin, a nucleoside analog containing a 1,2,4-triazole-3-carboxamide moiety, is a first-line

• drug for its treatment, however, its clinical use has been limited due to its side effects. Here, we designed two new nitroaryl-1,2,3-triazole triterpene derivatives as novel anti-RSV drugs. Their anti-RSV and cytotoxic activity were evaluated in vitro, RSV protein F gene effects by RT-PCR and

• with COVID-19 precautions; however, they state that less RSV cases now could reduce immunity and they fear there will be a rebound in infections after the pandemic [4][5][6][7]. As a therapeutic resource, ribavirin, a nucleoside analog prodrug containing a 1,2,4-triazole-3-carboxamide moiety (RBV

Scope of tetrazolo[1,5-a]quinoxalines in CuAAC reactions for the synthesis of triazoloquinoxalines, imidazoloquinoxalines, and rhenium complexes thereof

• Laura Holzhauer,
• Chloé Liagre,
• Olaf Fuhr,
• Nicole Jung and
• Stefan Bräse

Beilstein J. Org. Chem. 2022, 18, 1088–1099, doi:10.3762/bjoc.18.111

• ; tetrazole; triazole; Introduction Quinoxalines are amongst the most versatile N-heterocyclic compounds, combining a straightforward synthesis with a diverse set of possible functionalizations and a wide range of applications in drug development and materials sciences [1]. Different quinoxaline derivatives

• formation from tetrazolo[1,5-a]quinoxalines 1 is still limited. Triazole-linked N-heterocycles like pyridotriazoles and quinolinotriazoles exert a variety of favorable biological properties like anticancer and antimicrobial activities as well as protein kinase inhibition [10][13][14][15]. Moreover, a vast

• diversity of metal complexes incorporating 1,2,3-triazoles as ligands have been reported [16][17][18]. Triazole ligands with N-heterocycles such as Pyta (4-(2-pyridyl)-1,2,3-triazole) and related structures were employed to obtain novel metal complexes as catalysts [19][20] and imaging probes [21], as well

Electrochemical vicinal oxyazidation of α-arylvinyl acetates

• Yi-Lun Li,
• Zhaojiang Shi,
• Tao Shen and
• Ke-Yin Ye

Beilstein J. Org. Chem. 2022, 18, 1026–1031, doi:10.3762/bjoc.18.103

• ketones, such as cyclohexanone (see Supporting Information File 1 for details). As illustrated in Scheme 3, the synthetic utility of α-azidoketone was further evaluated [37][38]. Click reaction between 2-azido-1-phenylethan-1-one (2) and ethisterone (28) [39][40][41] readily afforded the target triazole

Synthesis of novel alkynyl imidazopyridinyl selenides: copper-catalyzed tandem selenation of selenium with 2-arylimidazo[1,2-a]pyridines and terminal alkynes

• Mio Matsumura,
• Kaho Tsukada,
• Kiwa Sugimoto,
• Yuki Murata and
• Shuji Yasuike

Beilstein J. Org. Chem. 2022, 18, 863–871, doi:10.3762/bjoc.18.87

• -triazoles [33]. Based on these findings, we examined the reaction of Cu-mediated AAC. The reaction of 4aa with benzyl azide in the presence of one equivalent of CuI and pentamethyldiethylenetriamine (PMDETA) in THF at 60 °C gave the desired 5-selanyl-1,2,3-triazole 8 in 72% yield. This reaction yielded a

• regioselective 1,3-dipolar azide–alkyne cycloaddition to form 5-selanyl-1,2,3-triazole. The investigation of the biological activity of the compounds obtained in this study and the application of this synthesis route using other heterocycles, instead of imidazopyridine, are currently underway in our laboratory

Heteroleptic metallosupramolecular aggregates/complexation for supramolecular catalysis

• Prodip Howlader and
• Michael Schmittel

Beilstein J. Org. Chem. 2022, 18, 597–630, doi:10.3762/bjoc.18.62

• -bonding, which would lead to catalytic quenching, a unique design strategy was applied. Instead of using a cis-blocked palladium(II) unit for self-assembly, Pd(NO3)2 was employed along with the triazole-based 0° clip 13. In a one-pot reaction, 12 and 13 in DMSO were treated with Pd(NO3)2 in a 1:1:1 ratio

• able to build a new catalytic machinery [100]. Hereunto, the two concepts RPI and ILC were combined in a synergistic manner, starting with rotor [Cu2(83)(91)]2+ (k298 = 46.0 kHz) that catalyzed the click reaction between the zinc porphyrin ligand 92 and the azide 93 furnishing triazole 94 (Figure 20

• state of the second click reaction, leads to an astounding synthetic efficiency, although there is a major distance mismatch between the copper(I) ions in [FeCu2(104)2]4+ and two triazole units of the rotaxane. For instance, the system [FeCu2(104)2]4+ (dCu–Cu = 34 Å) afforded the formation of both 109a

Synthesis of a new water-soluble hexacarboxylated tribenzotriquinacene derivative and its competitive host–guest interaction for drug delivery

• Man-Ping Li,
• Nan Yang and
• Wen-Rong Xu

Beilstein J. Org. Chem. 2022, 18, 539–548, doi:10.3762/bjoc.18.56

• larger cavity as compared to TBTQ-C6 due to the introduction of triazole rings. Two anticancer drug molecules, dimethyl viologen (MV) with a smaller size and DOX with a larger size, were selected as model anticancer agents for encapsulation by TBTQ-CB6 to form the host–guest complexes of TBTQ-CB6MV and

Chemistry of polyhalogenated nitrobutadienes, 17: Efficient synthesis of persubstituted chloroquinolinyl-1H-pyrazoles and evaluation of their antimalarial, anti-SARS-CoV-2, antibacterial, and cytotoxic activities

• Viktor A. Zapol’skii,
• Isabell Berneburg,
• Ursula Bilitewski,
• Melissa Dillenberger,
• Katja Becker,
• Stefan Jungwirth,
• Aditya Shekhar,
• Bastian Krueger and
• Dieter E. Kaufmann

Beilstein J. Org. Chem. 2022, 18, 524–532, doi:10.3762/bjoc.18.54

• Plasmodium has been developed and is reported in the literature [24]. Results and Discussion The vinylic SN reaction of 2-nitroperchlorobutadiene (1) with four equivalents of the azoles such as 1H-pyrazole, 1H-1,2,4-triazole, or 1H-benzotriazole affords similarly to [25] the corresponding 1,1

• concentration of 220 µM (50 µg/mL). Among the three 3-azolylpyrazoles 3a–c, the triazole derivative 3b showed the best activity with an EC50 = 0.2 ± 0.1 µM. The 3-aminopyrazoles 5a–o showed a rather broad activity range (EC50 = 0.5–4.1 µM) and were all less active than the azolylpyrazoles 3. The most active 3

BINOL as a chiral element in mechanically interlocked molecules

• Matthias Krajnc and
• Jochen Niemeyer

Beilstein J. Org. Chem. 2022, 18, 508–523, doi:10.3762/bjoc.18.53

• the thread (see Figure 16). The stereoselective binding of chiral anions by rotaxanes 64a/b was studied by 1H NMR titration experiments, using the dicationic macrocycle (S)-61-Me22+ (obtained by methylation of the triazole units in (S)-61) as a reference system. As guest molecules, the Boc-protected

Synthesis of novel [1,2,4]triazolo[1,5-b][1,2,4,5]tetrazines and investigation of their fungistatic activity

• Anna V. Korotina,
• Svetlana G. Tolshchina,
• Rashida I. Ishmetova,
• Natalya P. Evstigneeva,
• Natalya A. Gerasimova,
• Natalya V. Zilberberg,
• Nikolay V. Kungurov,
• Gennady L. Rusinov,
• Oleg N. Chupakhin and
• Valery N. Charushin

Beilstein J. Org. Chem. 2022, 18, 243–250, doi:10.3762/bjoc.18.29

• for their fungistatic activities against mycelial anthropophilic and zooanthropophilic dermatophytes (Trichophyton, Microsporum and Epidermophyton), which cause diseases of the skin and its appendages (hair, nails) (Table 1). In the series of compounds 3a–i, in which substituents in the triazole ring

Anomeric 1,2,3-triazole-linked sialic acid derivatives show selective inhibition towards a bacterial neuraminidase over a trypanosome trans-sialidase

• Peterson de Andrade,
• Sanaz Ahmadipour and
• Robert A. Field

Beilstein J. Org. Chem. 2022, 18, 208–216, doi:10.3762/bjoc.18.24

• natural substrate for sialidases and its chemical modification has been a useful approach to generate potent and selective inhibitors. Aiming at advancing the discovery of selective Trypanosoma cruzi trans-sialidase (TcTS) inhibitors, we have synthesised a small series of anomeric 1,2,3-triazole-linked

• differences in sialidases that need to be addressed in order to achieve selective inhibition. Keywords: inhibition; neuraminidase; sialic acid; trans-sialidase; 1,2,3-triazole; Introduction Amongst the diversity of glycans present in living organisms, N-acetylneuraminic acid (Neu5Ac, sialic acid) is

• series of C-2-modified sialic acid bearing a monosaccharide tethered via 1,2,3-triazole ring (sialylmimetic neoglycoconjugates) [19] that showed 67–91% inhibitory activity at 1 mM. We now envisaged replacing the monosaccharide moiety by (hetero)aromatic substituents (Figure 2A) expecting better

Peptide stapling by late-stage Suzuki–Miyaura cross-coupling

• Hendrik Gruß,
• Rebecca C. Feiner,
• Ridhiwan Mseya,
• David C. Schröder,
• Michał Jewgiński,
• Kristian M. Müller,
• Rafał Latajka,
• Antoine Marion and
• Norbert Sewald

Beilstein J. Org. Chem. 2022, 18, 1–12, doi:10.3762/bjoc.18.1

• ], disulfide- [13], thioether- [14][15][16][17][18][19][20], triazole- [21][22], oxime- [23] and hydrazone formation [24] as well as multicomponent reactions such as the Ugi- or Petasis reaction [25][26][27][28][29][30][31][32]. The content of helicity can moreover be changed by the introduction of a photo

Exfoliated black phosphorous-mediated CuAAC chemistry for organic and macromolecular synthesis under white LED and near-IR irradiation

• Azra Kocaarslan,
• Zafer Eroglu,
• Önder Metin and
• Yusuf Yagci

Beilstein J. Org. Chem. 2021, 17, 2477–2487, doi:10.3762/bjoc.17.164

• at 4.42 ppm and appearance of the new signal at 8.67 ppm corresponding to the triazole moiety confirmed successful click reaction under white LED exposure conditions after 4 h (Figure 3a). Kinetic studies conducted by 1H NMR analysis confirmed that the click reaction between benzyl azide and

• -Alk) and 9-(azidomethyl)anthracene (Az-2) as click components was investigated. The detailed 1H NMR spectrum of the resulting anthracene functional polymer (PCL-Anth) exhibited the characteristic signals of triazole and benzylic protons at 5.5 ppm and 8.70 ppm, respectively (Figure 4a). The obtained

• molecular weight region without contamination of the precursor polymers. The 1H NMR spectrum of the block copolymer displayed the characteristic peaks of both macromolecular segments. Additionally, the methylene protons adjacent to the triazole ring at 7.48 ppm were noted (Figure 5b). These results

Synthesis and antimicrobial activity of 1H-1,2,3-triazole and carboxylate analogues of metronidazole

• Satya Kumar Avula,
• Syed Raza Shah,
• Khdija Al-Hosni,
• Muhammad U. Anwar,
• Rene Csuk,
• Biswanath Das and
• Ahmed Al-Harrasi

Beilstein J. Org. Chem. 2021, 17, 2377–2384, doi:10.3762/bjoc.17.154

• -Wittenberg, Kurt-Mothes-Str. 2, d-06120, Halle (Saale), Germany 10.3762/bjoc.17.154 Abstract Herein, a series of novel 1H-1,2,3-triazole and carboxylate derivatives of metronidazole (5a–i and 7a–e) were synthesized and evaluated for their antimicrobial activity in vitro. All the newly synthesized compounds

• inhibiting effects compared to the activity of the parent compound. Amongst the tested compounds 5b, 5c, 5e, 7b and 7e displayed excellent potent antimicrobial activity. The current study has demonstrated the usefulness of the 1H-1,2,3-triazole moiety in the metronidazole skeleton. Keywords: antimicrobial

• agents; carboxylate analogues; 1H-1,2,3-triazole analogues; metronidazole; synthesis; Introduction Metronidazole (1) is an important antimicrobial agent which has been clinically used successfully for a long time. It was originally used for the treatment of infections caused by Trichomonas varginalis

Halides as versatile anions in asymmetric anion-binding organocatalysis

• Lukas Schifferer,
• Martin Stinglhamer,
• Kirandeep Kaur and
• Olga García Macheño

Beilstein J. Org. Chem. 2021, 17, 2270–2286, doi:10.3762/bjoc.17.145

• , but also to cation–H or π–π interactions. Some of the advantages of multidentate, supramolecular anion-binding catalysis were recently exploited by the Feringa group, who designed an anion-binding catalyst 86 that fuses the known triazole binding properties with a light-switchable molecular motor. In

• this way, they were not only able to control the folding of the triazole units through successive irradiation and thermal excitation, but they could also selectively control the stereochemical outcome of the benchmark reaction of 1-chloroisochromane (73) with silylketene acetals (Scheme 19) [92]. Such

(Phenylamino)pyrimidine-1,2,3-triazole derivatives as analogs of imatinib: searching for novel compounds against chronic myeloid leukemia

• Luiz Claudio Ferreira Pimentel,
• Lucas Villas Boas Hoelz,
• Henayle Fernandes Canzian,
• Frederico Silva Castelo Branco,
• Andressa Paula de Oliveira,
• Vinicius Rangel Campos,
• Floriano Paes Silva Júnior,
• Rafael Ferreira Dantas,
• Jackson Antônio Lamounier Camargos Resende,
• Anna Claudia Cunha,
• Nubia Boechat and
• Mônica Macedo Bastos

Beilstein J. Org. Chem. 2021, 17, 2260–2269, doi:10.3762/bjoc.17.144

• )pyrimidine-pyridine (PAPP) group as a pharmacophoric fragment, and these compounds were biologically evaluated. The synthesis of twelve new compounds was performed in three steps and assisted by microwave irradiation in a 1,3-dipolar cycloaddition to obtain 1,2,3-triazole derivatives substituted on carbon C

• -4 of the triazole nucleus. All compounds were evaluated for their inhibitory activities against a chronic myeloid leukemia cell line (K562) that expresses the enzyme tyrosine kinase BCR-Abl-1 and against healthy cells (WSS-1) to observe their selectivity. Three compounds showed promising results

• in the docking studies. Keywords: chronic myeloid leukemia; 1,3-dipolar cycloaddition; imatinib; (phenylamino)pyrimidine-pyridine; 1,2,3-triazole; Introduction Changes in tyrosine kinase proteins (TKPs), either by mutation or chromosomal translocation, can turn them into potent oncogenes

Chemical syntheses and salient features of azulene-containing homo- and copolymers

• Vijayendra S. Shetti

Beilstein J. Org. Chem. 2021, 17, 2164–2185, doi:10.3762/bjoc.17.139

• (146) and triazole-containing azulene methacrylate 150, whose synthesis is outlined in Scheme 25. The azulene-2-yl methacrylate (146) was synthesized in 75% yield from 2-hydroxyazulene (145) by treating it with methacryloyl chloride in chloroform (Scheme 25A). The 2-hydroxyazulene (145) was converted

• to 2-bromoazulene (147) and subsequently to the TMS acetylene derivative 148 suitable for the ‘click’ reaction [46] to obtain the triazole 149, which was eventually transformed into the triazole-containing azulene methacrylate monomer 150 (Scheme 25B). The monomers 146 and 150 were then subjected to

• -2-yl methacrylate (146) and (B) the triazole-containing azulene methacrylate 150. Synthesis of (A) azulene methacrylate polymer 151 and (B) triazole-containing azulene methacrylate polymer 152. Synthesis of azulene methyl methacrylate polymers 154, 155 (A and B) and azulene-sulfobetaine methacrylate