(E)-2-(2-Allylidenehydrazinyl)thiazole derivatives: Design, green synthesis, in silico and in vitro antimycobacterial and radical scavenging studies

HUBLIKAR, M., V. KADU, Jitender KUMAR, D. RAUT, S. SHIRAME, P. MAKAM and R. BHOSALE. (E)-2-(2-Allylidenehydrazinyl)thiazole derivatives: Design, green synthesis, in silico and in vitro antimycobacterial and radical scavenging studies. Archiv der Pharmazie. Weinheim: Verlag Chemie, 2020, vol. 353, No 7, p. 2000003-2000014. ISSN 0365-6233. Available from: https://dx.doi.org/10.1002/ardp.202000003.

Basic information

• Original name: (E)-2-(2-Allylidenehydrazinyl)thiazole derivatives: Design, green synthesis, in silico and in vitro antimycobacterial and radical scavenging studies
• Authors: HUBLIKAR, M., V. KADU, Jitender KUMAR (356 India, guarantor, belonging to the institution), D. RAUT, S. SHIRAME, P. MAKAM and R. BHOSALE.
• Edition: Archiv der Pharmazie. Weinheim, Verlag Chemie, 2020, 0365-6233.

Other information

• Original language: English
• Type of outcome: Article in a journal
• Field of Study: 30104 Pharmacology and pharmacy
• Country of publisher: Germany
• Confidentiality degree: is not subject to a state or trade secret
• WWW: URL
• Impact factor: Impact factor: 3.751
• RIV identification code: RIV/00216224:14740/20:00118399
• Organization unit: Central European Institute of Technology
• Doi: http://dx.doi.org/10.1002/ardp.202000003
• UT WoS: 000530383800001
• Keywords in English: (E)-2-(2-allylidenehydrazinyl)thiazoles; anti-inflammatory; antituberculosis; radical scavenger; beta-ketoacyl-ACP synthase
• Tags: rivok
• Tags: International impact, Reviewed

Abstract

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 H(37)Rv by the microplate Alamar Blue assay. The results reveal that compound 6 was potent, with a MIC value of 6.5 mu g/ml, and showed better interactions with the KasA protein with binding free energy (Delta G) 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-mu g/ml concentration.