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(E)-2-(2-Allylidenehydrazinyl)thiazole derivatives: Design, green synthesis, in silico and in vitro antimycobacterial and radical scavenging studies
M. Hublikar, V. Kadu, JK. Dublad, D. Raut, S. Shirame, P. Makam, R. Bhosale
Language English Country Germany
Document type Journal Article
- MeSH
- Antitubercular Agents chemical synthesis chemistry pharmacology MeSH
- Microbial Sensitivity Tests MeSH
- Models, Molecular MeSH
- Molecular Structure MeSH
- Mycobacterium tuberculosis drug effects MeSH
- Drug Design * MeSH
- Free Radical Scavengers chemical synthesis chemistry pharmacology MeSH
- Thiazoles chemical synthesis chemistry pharmacology MeSH
- Dose-Response Relationship, Drug MeSH
- Structure-Activity Relationship MeSH
- Publication type
- Journal Article MeSH
By understanding the rampant infections of Mycobacterium tuberculosis (Mtb) and inflammations caused due to the generation of radical species during the Mtb infection, a series of (E)-2-(2-allylidenehydrazinyl)thiazole derivatives, with dual-action properties, was designed. The molecules were designed with a considerable variation in LogP, one of the critical parameters in physicochemical properties, and analyzed for their drug-likeness. For the synthesis, a simple, green, and multicomponent one-pot synthesis method was developed. The in vitro inhibition potentials were evaluated against Mtb H37 Rv by the microplate Alamar Blue assay. The results reveal that compound 6 was potent, with a MIC value of 6.5 µg/ml, and showed better interactions with the KasA protein with binding free energy (ΔG) of -9.4 kcal/mol. Also, the radical scavenging properties were studied to establish the dual-action properties of the molecules. Compound 9 exhibited promising antioxidant and nitric oxide radical scavenging activities, with 81.7% and 81.0%, respectively, at 1,000-μg/ml concentration.
References provided by Crossref.org
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