Benzimidazole: a promising pharmacophore

Shah, Kamal; Chhabra, Sumit; Shrivastava, Sushant K.; Mishra, Pradeep

doi:10.1007/s00044-013-0476-9

Cited by 105 publications

(58 citation statements)

References 68 publications

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“…[2,3] Their derivatives display a broad spectrum of different biological features such as anticancer, antiviral, antibacterial, antifungal, antiinflammatory etc. [4][5][6] In our research group we have published several publications regarding antiproliferative and antitumor activity of versatile benzimidazole and benzothiazole derivatives bearing different amidino supstituents. [7,8] Among all amidino substituted benzazole derivatives, the ones with the cyclic amidino substituent, namely 2-imidazolinyl group, showed the most significant antiproliferative activity in vitro with IC50 values in submicromolar range of concentrations.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antioxidative Potency of Novel Amidino Substituted Benzimidazole and Benzothiazole Derivatives

Racané¹,

Cindrić²,

Perin³

et al. 2017

Croat. Chem. Acta

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Herein we present the synthesis of versatile amidino substituted benzothiazole 3-10 and benzimidazole 12-19 derivatives substituted with the variable number of hydroxy and methoxy groups. Furthermore, the synthesized compounds were explored for their antioxidative activity in vitro by using three biological assays, namely DPPH, ABTS and FRAP. The obtained results indicated that the variable number of hydroxy groups together with the type of the amidino substituent strongly influenced the antioxidative activity and reducing power of tested compounds. The most promising antioxidative activity showed trihydroxy substituted compounds 6, 10, 15 and 19. In general, it was noticed that unsubstituted amidino group induced the more pronounced activity in comparison to derivatives bearing 2-imidazolinyl group.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Antioxidative Potency of Novel Amidino Substituted Benzimidazole and Benzothiazole Derivatives

Racané¹,

Cindrić²,

Perin³

et al. 2017

Croat. Chem. Acta

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“…There has been an increased interest in the investigation of antimicrobial activities of 2‐substituted benzofuran derivatives . Also, benzimidazole derivatives show antiparasitic, antibacterial, anthelmintic, analgesic, anti‐inflammatory, anticancer and antitubercular activities. The structural diversity of the moieties as well as their biological and pharmaceutical importance have motivated research to develop new classes of benzofuran‐substituted benzimidazoles.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and spectroscopic characterization of transition metal complexes derived from novel benzofuran hydrazone chelating ligand: DNA cleavage studies and antimicrobial activity with special emphasis on antituberculosis

Kokare

Naik

Nevrekar

et al. 2016

Applied Organom Chemis

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Mononuclear divalent complexes of Co, Ni, Cu and Zn derived from a benzofuran‐based novel hydrazone tridentate ligand were synthesized and characterized using various spectroscopic methods. Elemental analysis reveals that the metal‐to‐ligand ratio is 1:2 which is supported by mass spectrometry results. Conductivity measurements suggest that all the complexes are non‐electrolytic in nature. The ligand and complexes were evaluated for their antimicrobial potency. Bioassay of all hydrazone chelates shows enhanced activity as compared to that of the ligand. The complex with cobalt ion as the metal centre shows better activity against fungi than the standard. Also, ligand and complexes were screened for antituberculosis activity; some analogues (Ni, Cu, Zn) are eight times more active than the standard. Both ligand and complexes show moderate ability to cleave calf thymus DNA. Copyright © 2015 John Wiley & Sons, Ltd.

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“…Phts are lipophilic and neutral molecules that can easily cross biological membranes, and possess anti-microbial [30] and anti-inflammatory [31] activities. Likewise, N-containing heterocyclic moieties such as benzimidazole and triazole, which are found in various natural and synthetic alkaloids, also possess diverse therapeutic applications [32,33]. We have shown that Pht analogues embedded with benzimidazole and flexible triazoles are potent agents against Plasmodium falciparum (Pf 3D7) and Pf W2 malaria strains with 50% inhibitory concentration (IC 50 ) values of~0.7 µM [34].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Bioactivity of Phthalimide Analogs as Potential Drugs to Treat Schistosomiasis, a Neglected Disease of Poverty

et al. 2020

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The neglected tropical disease, schistosomiasis, is caused by trematode blood flukes of the Schistosoma genus and infects approximately 200 million people worldwide. With just one partially effective drug available for disease treatment, new drugs are urgently needed. Herein, a series of 47 phthalimide (Pht) analogues possessing high-value bioactive scaffolds (i.e., benzimidazole and 1,2,3,-triazoles) was synthesized by click-chemistry. Compounds were evaluated for anti-schistosomal activity in culture against somules (post-infective larvae) and adults of Schistosoma mansoni, their predicted ADME (absorption, distribution, metabolism, and excretion) properties, and toxicity vs. HepG2 cells. The majority showed favorable parameters for surface area, lipophilicity, bioavailability and Lipinski score. Thirteen compounds were active at 10 µM against both somules and adults (6d, 6f, 6i-6l, 6n-6p, 6s, 6r', 6t' and 6w). Against somules, the majority caused degeneracy and/or death after 72 h; whereas against adult parasites, five compounds (6l, 6d, 6f, 6r' and 6s) elicited degeneracy, tegumental (surface) damage and/or death. Strongest potency against both developmental stages was recorded for compounds possessing n-butyl or isobutyl as a linker, and a pentafluorophenyl group on triazole. Apart from five compounds for which anti-parasite activity tracked with toxicity to HepG2 cells, there was apparently no toxicity to HepG2 cells (EC 50 values ≥50 µM). The data overall suggest that phthaloyl-triazole compounds are favorable synthons for additional studies as anti-schistosomals.

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Benzimidazole: a promising pharmacophore

Cited by 105 publications

References 68 publications

Synthesis and Antioxidative Potency of Novel Amidino Substituted Benzimidazole and Benzothiazole Derivatives

Synthesis and Antioxidative Potency of Novel Amidino Substituted Benzimidazole and Benzothiazole Derivatives

Synthesis and spectroscopic characterization of transition metal complexes derived from novel benzofuran hydrazone chelating ligand: DNA cleavage studies and antimicrobial activity with special emphasis on antituberculosis

Synthesis and Bioactivity of Phthalimide Analogs as Potential Drugs to Treat Schistosomiasis, a Neglected Disease of Poverty

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