Novel benzimidazole–oxadiazole hybrid molecules as promising antimicrobial agents

Shruthi, N.; Poojary, Boja; Kumar, Vinod; Hussain, Mumtaz Mohammed; Rai, Vaishali; Pai, Vidya; Bhat, Mahima; Revannasiddappa, B. C.

doi:10.1039/c5ra23282a

Cited by 34 publications

(11 citation statements)

References 46 publications

(31 reference statements)

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“…In the recent decades, continued attention has been focused on the heterocyclic compounds owing to their major roles in biological processes and pharmaceuticals . Benzimidazole‐oxadiazole hybrids have showed promising MIC against both Gram‐positive, Gram‐negative bacteria and also against Mycobacterium tuberculosis . Cappoen et al., synthesized diazene derivatives with 90% growth inhibition against the clinically relevant mycobacterial species such as Mycobacterium bovis , Mycobacterium avium , and Mycobacterium ulcerans .…”

Section: Introductionmentioning

confidence: 99%

Antibacterial and antitubercular evaluation of dihydronaphthalenone‐indole hybrid analogs

Kumar

et al. 2017

Chem Biol Drug Des

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A new series of indole appended dihydronaphthalenone hybrid analogs (5a-t) have been synthesized through the Lewis acid catalyzed Michael addition of indoles to the arylidene/hetero arylidene ketones. All the synthesized derivatives are well characterized through the H-NMR, C-NMR, HRMS spectroscopic techniques, compound 5r was further confirmed through single crystal X-ray analysis and screened for antibacterial and antitubercular activities. Among the synthesized compounds, the minimum inhibition concentration of 5l (against Escherichia coli) and 5o & 5p (against E. coli & Staphylococcus aureus) was found to be as low as 3.12 μg/ml as compared to the standard antibacterial drug ciprofloxacin 2.5 μg/ml. In antitubercular activity, compounds 5o and 5p with minimum inhibition concentration 6.25 μg/ml were found to be comparable with that of the drugs Pyrazinamide 5 μg/ml and Streptomycin 5 μg/ml. Compounds 5i, 5j, 5m, 5n, 5q, and 5r also showed promising activity against group of organisms tested.

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Section: Introductionmentioning

confidence: 99%

Antibacterial and antitubercular evaluation of dihydronaphthalenone‐indole hybrid analogs

Kumar

et al. 2017

Chem Biol Drug Des

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“…Base hydrolysis of the compound 2 yielded the title compound (3). The synthesis of ethyl 4-(methylamino)-3-nitrobenzoate (1) was explained in our earlier report [19].…”

Section: Resultsmentioning

confidence: 99%

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2017

MOJBOC

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“…The most commonly used ADME model is Lipinski's “rule of five” which helps to identify suitable bioactive drug compounds . For a potential drug molecule to be a therapeutic agent, it should satisfy Lipinski's Rule of Five along with high oral bioavailability, which is decided by ADME (Absorption, Distribution, Metabolism and Elimination) profile . This rule predicts that the active compound should have a molecular weight (MW) less than 500 and the partition coefficient (logP) should be ≤5.…”

Section: Molecular Dockingmentioning

confidence: 99%

Synthesis, Characterization, Molecular Docking Studies and Biological Evaluation of Some Conjugated Quinazoline‐Sulfonamide Scaffold

Kumar¹,

Kudva²,

Bharath³

et al. 2018

ChemistrySelect

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A series of sulfonamides containing 4-aminoquinazoline scaffolds 7 a-7 l was synthesized, characterized and evaluated for their in vitro antitubercular, antimicrobial and anticancer activity. The compounds with 4-nitrophenyl (7 c), 3-trifluoromethylphenyl (7 f) and 5-chloro-pyridin-2-yl (7 h) derivatives have shown potent antitubercular activity against Mycobacterium tuberculosis H37Rv strain and the activity was two-fold higher than the standard drug Ciprofloxacin. The compounds with 4chlorophenyl (7 a), pyridin-2-yl (7 g), 5-chloro-pyridin-2-yl (7 h) and pyrimidin-2-yl (7 i, 7 j and 7 k) derivatives were observed as excellent antimicrobial agents. The preliminary toxicity of selected potent compounds was also tested on Red Blood Cells by hemolytic assay and found to be non-toxic even at higher concentrations. Compounds with 4-nitrophenyl (7 c) and 4fluorophenyl (7 e) substitutions emerged as potent molecules against MDA-MB-231 cell line. ADME (Absorption, Distribution, Metabolism and Excretion) screening study revealed that the compounds are strong candidates for antitubercular activity with good ADME parameters. In addition, the structure and antitubercular activity relationship were further supported by molecular docking studies of the active compounds against the DNA topoisomerase II (5BTC) enzyme of M. tuberculosis.[a] A.

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Novel benzimidazole–oxadiazole hybrid molecules as promising antimicrobial agents

Abstract: In the present study, we describe the design and expeditious synthesis of novel 2-aryl-5-(3-aryl-[1,2,4]-oxadiazol-5-yl)-1-methyl-1H-benzo[d]imidazole hybrid molecules as promising antimicrobial agents.

Cited by 34 publications

References 46 publications

Antibacterial and antitubercular evaluation of dihydronaphthalenone‐indole hybrid analogs

Antibacterial and antitubercular evaluation of dihydronaphthalenone‐indole hybrid analogs

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Synthesis, Characterization, Molecular Docking Studies and Biological Evaluation of Some Conjugated Quinazoline‐Sulfonamide Scaffold

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