Ultrasound-assisted synthesis of auxiliary pyrazoline integrated thiazole, thiazolone derivative and their biological evaluation

In this paper, we describe a simplecatalyst-free protocol for the synthesis of thiazole, thiazolone integrated pyrazole derivatives, under ultra-sonication technique. Thiazolone derivatives ۵a, ۵e, ۵i, ۵d, ۵h, ۵l were derived from [۲+۳] cyclocondensation reaction between carbothioamide pyrazoline (۴ a-c) as S-N bi-nucleophile with DMAD/DEAD. The target molecules ۵b, ۵f, ۵j,۵c, ۵g, ۵k weresynthesized by reaction of (۴ a-c) with substituted bromoethanone. Formation of the products was confirmed by FT-IR, ۱H-NMR, ۱۳C-NMR, LC-MS and X-ray analysis. Docking studies were carried out against the antimicrobial target (۳UDI) to know interaction of the molecules (ligands) with the docked target. Among the docked compounds thiazolone derivative ۵d showed the minimum binding energy of -۹.۰۸ kJ/mol with ligand efficiency of -۰.۲۳. All the synthesized compounds were examined primarily for their in-vitro antibacterial and antioxidant activity (IC۵۰). Compound ۵g (۱۸±۰.۰) and ۵d (۱۹.۵±۰.۵) showed significant bacterial inhibition against E.coli and S.aureus. Compound ۵k (۱۶.۵۷) were showed substantial DPPH free radical inhibition activity as compared to the reference drug Ascorbic acid.

کلیدواژه ها:

Thiazole pyrazoline ، Cyclocondensation ، Hantzsch reaction ، Ultra-sonication ، antibacterial ، Antioxidant activity