Synthesis of 2,5-disubstituted-1,3,4-thiadiazole derivatives from (2S)-3-(benzyloxy)-2-[(tert-butoxycarbonyl) amino] propanoic acid and evaluation of anti-microbial activity

Abstract

The new compounds AP-1 to AP-10 were synthesized from starting material (2S)-3-(benzyloxy)-2-[(tert-butoxycarbonyl) amino]propanoic acid (1). The intermediate 2,5-disubstituted-1,3,4-thiadiazole amine (5) was prepared by coupling of (2S)-3-(Benzyloxy)-2-[(tert-butoxycarbonyl) amino]propanoic acid (1) with pyridine-2-carboxylic acid hydrazide (2) in the presence of carbonyldiimidazole (CDI) followed by 1,3,4-thiadiazole ring formation via diacylhydrazines derivative (3) and deprotection with shorter reaction time and excellent yield. The structures of new compounds were confirmed by spectral analysis. The series of new synthesized compounds AP-1 to AP-10 were evaluated for their anti-microbial activities in vitro and compounds AP-1, AP-3, AP-4, and AP-10 showed strong activities against all tested microorganisms.

Graphical Abstract

Keywords:

• Anti-microbial
• carbonyldiimidazole
• evaluation
• pyridine-2-carboxylic acid hydrazide
• 1,3,4-thiadiazole

Acknowledgments

The authors gratefully acknowledge the Director, UGC, WRO Pune for providing financial assistance and thankful to Principal, Shivaji Arts, Commerce and Science College Kannad, District Aurangabad (M.S.) for providing research laboratory facilities. The authors are grateful to Dr. Arvind Merwade, AVP of Wockhardt Research Centre, Aurangabad and Dr. Dinanath Deoram Patil, Principal, Sahakar Maharshi Bhausaheb Santuji Thorat Arts, Science and Commerce College, Sangamner for motivation and kind support during work.

Disclosure statement

No potential conflict of interest was reported by the author(s).