Tetrazole and triazole as bioisosteres of carboxylic acid: Discovery of diketo tetrazoles and diketo triazoles as anti-HCV agents

Song, Wuhui; Liu, Mingming; Zhong, Dongwei; Zhu, Yelin; Bosscher, Mike; Zhou, Lu; Ye, Deyong; Yuan, Zhenghong

doi:10.1016/j.bmcl.2013.06.045

Cited by 29 publications

(14 citation statements)

References 18 publications

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“…Our approach recognizes that, while the thione is fundamental for binding to MBLs through the coordination of the Zn ions (the triazole-thio moiety is common in several MBLs inhibitors [30][31][32][33]), the triazole itself may provide the KPC-2 binding site with the necessary electron-donor requirements for its interactions with key residues such as Ser70, Lys73, Ser130 and Asn132. Moreover, triazole is a bioisostere of the carboxylic group and is, thus, able to make favourable interactions in the deepest part of the class A BL binding site [36][37][38][39].…”

Section: Compounds Design and Synthesismentioning

confidence: 99%

4-Amino-1,2,4-triazole-3-thione as a Promising Scaffold for the Inhibition of Serine and Metallo-β-Lactamases

et al. 2020

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The emergence of bacteria that co-express serine- and metallo- carbapenemases is a threat to the efficacy of the available β-lactam antibiotic armamentarium. The 4-amino-1,2,4-triazole-3-thione scaffold has been selected as the starting chemical moiety in the design of a small library of β-Lactamase inhibitors (BLIs) with extended activity profiles. The synthesised compounds have been validated in vitro against class A serine β−Lactamase (SBLs) KPC-2 and class B1 metallo β−Lactamases (MBLs) VIM-1 and IMP-1. Of the synthesised derivatives, four compounds showed cross-class micromolar inhibition potency and therefore underwent in silico analyses to elucidate their binding mode within the catalytic pockets of serine- and metallo-BLs. Moreover, several members of the synthesised library have been evaluated, in combination with meropenem (MEM), against clinical strains that overexpress BLs for their ability to synergise carbapenems.

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Section: Compounds Design and Synthesismentioning

confidence: 99%

4-Amino-1,2,4-triazole-3-thione as a Promising Scaffold for the Inhibition of Serine and Metallo-β-Lactamases

et al. 2020

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“…Red hygroscopic; yield: 39%; Rf: 0.91 (CH2Cl2/MeOH 8/2)/silica. IR (KBr, cm −1 ): ν (OH) = 3434 cm −1 ; ν (C=O) = 1620 cm −1 ; ν (enolic C=C) = 1468; 1 H-NMR (CDCl3): δ 2.13 (s, 3H, -CH3); 6.06 (s, 1H, enol, C-H) ;6.52 (m,1H,7.14 (d,1H,7.55 (m,1H, 15;H,5.30. Found: C,63.25,H,.…”

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confidence: 99%

Synthesis of Novel β-Keto-Enol Derivatives Tethered Pyrazole, Pyridine and Furan as New Potential Antifungal and Anti-Breast Cancer Agents

et al. 2015

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Abstract:Recently, a new generation of highly promising inhibitors bearing β-keto-enol functionality has emerged. Reported herein is the first synthesis and use of novel designed drugs based on the β-keto-enol group embedded with heterocyclic moieties such as pyrazole, pyridine, and furan, prepared in a one-step procedure by mixed Claisen condensation. All the newly synthesized compounds were characterized by FT-IR, 1 H-NMR, 13 C-NMR, ESI/LC-MS, elemental analysis, and evaluated for their in vitro antiproliferative activity against breast cancer (MDA-MB241) human cell lines and fungal strains (Fusarium oxysporum f.sp albedinis FAO). Three of the synthesized compounds showed potent activity against fungal strains with IC 50 values in the range of 0.055-0.092 µM. The results revealed that these compounds showed better IC 50 values while compared with positive controls.

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“…Anti-HCV activity was assessed by measuring the EGFP autofluorescence in HCV infected Huh-7.5 cell lines [22,23]. The values represent a mean of triplicate results of the declined percentage of EGFP autofluorescence activity.…”

Section: Resultsmentioning

confidence: 99%

“…Anti-HCV activities were evaluated in vitro in an authentic HCV infection system in human hepatoma cell lines by measuring the EGFP autofluorescence as described in the literature [22,23]. Compound 6b and chlorogenic acid were tested at a final concentration of 100 μg/mL.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Anti-HCV, Antioxidant and Reduction of Intracellular Reactive Oxygen Species Generation of a Chlorogenic Acid Analogue with an Amide Bond Replacing the Ester Bond

Wang

Hattori

et al. 2016

Molecules

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Chlorogenic acid is a well known natural product with important bioactivities. It contains an ester bond formed between the COOH of caffeic acid and the 3-OH of quinic acid. We synthesized a chlorogenic acid analogue, 3α-caffeoylquinic acid amide, using caffeic and quinic acids as starting materials. The caffeoylquinc acid amide was found to be much more stable than chlorogenic acid and showed anti-Hepatitis C virus (anti-HCV) activity with a potency similar to chlorogenic acid. The caffeoylquinc acid amide potently protected HepG2 cells against oxidative stress induced by tert-butyl hydroperoxide.

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Tetrazole and triazole as bioisosteres of carboxylic acid: Discovery of diketo tetrazoles and diketo triazoles as anti-HCV agents

Cited by 29 publications

References 18 publications

4-Amino-1,2,4-triazole-3-thione as a Promising Scaffold for the Inhibition of Serine and Metallo-β-Lactamases

4-Amino-1,2,4-triazole-3-thione as a Promising Scaffold for the Inhibition of Serine and Metallo-β-Lactamases

Synthesis of Novel β-Keto-Enol Derivatives Tethered Pyrazole, Pyridine and Furan as New Potential Antifungal and Anti-Breast Cancer Agents

Synthesis, Anti-HCV, Antioxidant and Reduction of Intracellular Reactive Oxygen Species Generation of a Chlorogenic Acid Analogue with an Amide Bond Replacing the Ester Bond

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