Synthesis and evaluation of biological activities of 4-cyclopropyl-5-(2-fluorophenyl) arylhydrazono-2,3-dihydrothiazoles as potent antioxidant agents

Abstract

A new series of 4-cyclopropyl-5-(2-fluorophenyl)arylhydrazono-2,3-dihydrothiazole derivatives was synthesized via the reaction of prepared thiosemicarbazones with 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone in the presence of Et₃N as a catalyst through a semi Hantzsch cyclization. The optimized reaction conditions for this one-pot reaction were achieved. The products were obtained in short reaction times, high yields and high purities. Antioxidant activity of products was evaluated using DPPH (2,2-diphenyl-2-picrylhydrazyl) and ABTS 2,2-azinobis(3-ethylbenzothiazoline-sulfonate) assays. Products showed higher antioxidant activity using the ABTS method. Compounds 5c and 5g showed lower IC₅₀ values compared with ascorbic acid as a standard. Compounds 5a–5h possessed moderate to high antioxidant activity by both methods. Also, antibacterial activity of 5a–5h was evaluated against gram-positive and gram-negative bacterial strains. None of the compounds inhibited A. hydrophila, while they had moderate to low inhibitory activity against other tested bacterial strains.

GRAPHICAL ABSTRACT

KEYWORDS:

• Hydrazinyl thiazole
• 2-bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanone
• antioxidant
• DPPH
• ABTS
• antibacterial

Acknowledgements

The authors gratefully thank the assistance of Dr Zohreh Ramezanpour and Miss Somaie Rasouli Dogaheh for help in running biological assays.

Disclosure statement

No potential conflict of interest was reported by the authors.