Synthesis, biological evaluation and molecular docking of novel coumarin incorporated triazoles as antitubercular, antioxidant and antimicrobial agents

Shaikh, Mubarak H.; Subhedar, Dnyaneshwar D.; Shingate, Bapurao B.; Khan, Firoz A. Kalam; Sangshetti, Jaiprakash N.; Khedkar, Vijay M.; Nawale, Laxman; Sarkar, Dhiman; Navale, Govinda R.; Shinde, Sandip S.

doi:10.1007/s00044-016-1519-9

Cited by 69 publications

(45 citation statements)

References 42 publications

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“…Steric interactions were observed at the Gly133, Asn385 and Lys367 residues with the trifluoromethylbenzene moiety, interactions of the two-carbon Cys387s with respect to the benzene group and interactions of the Gly117 residue with the nitrogen of the heterocyclic moiety. Recently, studies by Shaikh et al (2016) has shown that its benzothiazinone derivatives have similar binding modes reported in this study, from which the hydrogen bonding acts as a support and guides the position of the compound in the active site, favoring the other steric interactions with the receptor. In addition, the interactions of the benzene ring, correlating the pi-pi interaction, favored the activity of compound 11a in the active site of DprE1.…”

Section: Mol2net 2015supporting

confidence: 66%

Molecular docking studies of benzothiazinone derivatives in the search for new tuberculostatic agents

Viana

Scotti

2017

Proceedings of MOL2NET 2017, International Conference on Multidisciplinary Sciences, 3rd Edition

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Despite the efforts to reduce the rate of infection, the resurgence of Tuberculosis, accompanied by strains of Mycobacterium tuberculosis, calls attention to the search for new drugs that can bypass resistance mechanisms. Among the strategies for the development of antitubercular lead compounds, benzothiazinones (BTZ) are included, with highly selective mechanism of action of DprE1 flavoenzyme. We studied four compounds in the antituberculosis activity (IC 50 values between 0.029 -0.060 μg/ml). These derivatives were subjected to energy minimization and Molecular Docking calculations in the software Molegro Virtual Docker, from which the binding free energy calculations showed that the suggested compounds had better binding affinity with DprE1 when compared to PBTZ169, a crystallized inhibitor of DprE1. Our results showed that the compounds showed similar crucial binding interactions between the compounds, which may determine that there was molecular rearrangement within the active site itself. Thus, our studies evidenced the probable interactions that favor the activity of the derivatives, as well as other interactions of the compounds with other residues not reported in the literature, and these may act as lead compounds in the development of new antituberculosis drugs.

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Section: Mol2net 2015supporting

confidence: 66%

Molecular docking studies of benzothiazinone derivatives in the search for new tuberculostatic agents

Viana

Scotti

2017

Proceedings of MOL2NET 2017, International Conference on Multidisciplinary Sciences, 3rd Edition

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“…In view of the resourceful importance of both coumarins and 1,2,4‐triazoles thione in antimicrobial and antitubercular activity, it is beneficial to combine these two heterocyclic systems in a single hybrid compound via a synthetic methodology and enhancing the antimicrobial and antitubercular activity. The structurally related some 1,2,4‐triazoles thione (A, B, C and D Figure ) and coumarin derivatives (E and F Figure ), with interesting antibacterial and antitubercular activity is presented in Figure .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antitubercular and Antimicrobial Activity of 1,2,4‐Triazolidine‐3‐thione Functionalized Coumarin and Phenyl Derivatives and Molecular Docking Studies

et al. 2019

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Tuberculosis (TB) is still a demanding worldwide health problem and mycobacterium tuberculosis (MTB) remains one of the most toxic human pathogens. In pursuit of searching new antitubercular and antimicrobial agents, substituted coumarin and phenyl‐1,2,4‐triazolidine‐3‐thiones 4a‐i and 5a‐e have been synthesized and evaluated for their antitubercular and antimicrobial activities. Most of the Substituted coumarin and phenyl‐1,2,4‐triazolidine‐3‐thiones showed promising activity against Mycobacterium tuberculosis (H37Rv). The title compounds have exhibited excellent in vitro antibacterial activity against the S.aureus, Bacillus sps and E.coli with the values of low MIC ranging from of 0.4 to 1.6 μg/mL. In vitro antifungal activity shown that the compounds 4a‐i and 5a‐e are excellent antifungal agents against Candida albicans, Aspergillus flavus, Aspergillus niger and Aspergillus fumigate fungal stains with the values of low minimum inhibitory concentrations (MIC) ranging from 0.4 to 6.25 μg/mL. Molecular docking study was performed for all the synthesized compounds with E.coli as antibacterial and Mycobacterium tuberculosis DprE1 as antituberculosis.

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“…The coumarin–1,2,3‐triazole hybrids 1 (minimum inhibitory concentration [MIC]: 2–128 µg/ml) and 2 (MIC: 2–128 µg/ml) showed considerable activity against Gram‐positive bacteria, Staphylococcus aureus ( S. aureus ), Micrococcus luteus ( M. luteus ), and Bacillus cereus ( B. cereus ), and Gram‐negative strains, Escherichia coli ( E. coli ), Pseudomonas fluorescens , and Flavobacterium devorans . [ 41 ] Moreover, these hybrids also displayed comparable or even better antitubercular, antioxidant, and antifungal efficacy in comparison with reference drugs. The antibacterial SAR revealed that hybrids with substituent at para position were more potent than the corresponding ortho position analogs, and nitro group was most favorable to the activity.…”

Section: Coumarin–triazole Hybridsmentioning

confidence: 99%

“…[ 42 ] The movement of 1,2,3‐triazole fragment from C‐7 position of coumarin moiety to C‐6 position was also tolerated, and hybrids 4a,b (inhibition zone: 23 and 30 mm at 50 µg/ml) exhibited potential activity against S. aureus and E. coli . [ 43 ] Particularly, hybrids 1a (MIC: 2–16 µg/ml) and 2a (MIC: 2–8 µg/ml) were comparable to the references ampicillin, kanamycin, and chloramphenicol (MIC: 2–16 µg/ml) against the six tested bacteria, [ 41 ] implying the potential applicability of these hybrids as antibacterial agents.…”

Section: Coumarin–triazole Hybridsmentioning

confidence: 99%

Coumarin‐containing hybrids and their antibacterial activities

Feng

Zhang

Yang

et al. 2020

Archiv der Pharmazie

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Infections caused by Gram-positive and -negative bacteria are one of the foremost causes of morbidity and mortality globally. Antibiotics are the mainstay of therapy for bacterial infections, but the emergence and wide spread of drug-resistant pathogens have already become a huge issue for public healthcare systems. The coumarin moiety, which is ubiquitous in nature, could bind to the B subunit of DNA gyrase in bacteria and inhibit DNA supercoiling by blocking the ATPase activity; hence, coumarin derivatives possess potential antibacterial activity. Several coumarin-containing hybrids such as coumermycin A1, clorobiocin, and novobiocin have already been used in clinical practice for the treatment of various bacterial infections; thus, it is conceivable that hybridization of the coumarin moiety with other antibacterial pharmacophores may provide opportunities for the development of novel antibiotics. This review outlines the advances in coumarin-containing hybrids with antibacterial potential in the recent 5 years and the structure-activity relationships are also discussed. K E Y W O R D S antibacterial, coumarin, hybrid compounds, structure-activity relationships

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Synthesis, biological evaluation and molecular docking of novel coumarin incorporated triazoles as antitubercular, antioxidant and antimicrobial agents

Cited by 69 publications

References 42 publications

Molecular docking studies of benzothiazinone derivatives in the search for new tuberculostatic agents

Molecular docking studies of benzothiazinone derivatives in the search for new tuberculostatic agents

Synthesis, Antitubercular and Antimicrobial Activity of 1,2,4‐Triazolidine‐3‐thione Functionalized Coumarin and Phenyl Derivatives and Molecular Docking Studies

Coumarin‐containing hybrids and their antibacterial activities

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