(E)‐2‐(2‐Allylidenehydrazinyl)thiazole derivatives: Design, green synthesis, in silico and in vitro antimycobacterial and radical scavenging studies. Issue 7 (5th May 2020)

• Record Type: Journal Article
• Authors: Hublikar, Mahesh; Kadu, Vikas; Dublad, Jitender Kumar; Raut, Dattatraya; Shirame, Sachin; Makam, Parameshwar; Bhosale, Raghunath
• Is Part Of: Archiv der Pharmazie. Volume 353:Issue 7(2020)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2020-05-05
• Subjects: (E)‐2‐(2‐allylidenehydrazinyl)thiazoles -- anti‐inflammatory -- antituberculosis -- radical scavenger -- β‐ketoacyl‐ACP synthase; Pharmaceutical chemistry -- Periodicals; Pharmacology -- Periodicals; 615.19
• DOI: 10.1002/ardp.202000003
• Languages: English
• ISSNs: 0365-6233

Abstract

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 Log P, 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 (Δ 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‐μg/ml concentration. Abstract : A series of ( E )‐2‐(2‐allylidenehydrazinyl)thiazole derivatives, with dual‐action properties, was designed and investigated by in vitro antimycobacterial and radical scavenging assays, and docking studies with the β ‐ketoacyl‐ACP synthase protein. 2‐{(2 E )‐2‐[(2 Z )‐3‐Chloro‐3‐(4‐chlorophenyl)prop‐2‐en‐1‐ylidene]hydrazinyl}‐4‐(4‐nitrophenyl)‐1, 3‐thiazole 6 displayed a promising antituberculosis activity.