Synthesis and structural analysis of persuasive antibacterial agents and enzyme inhibitors derived from 5-(1-(4-Tosyl)piperidin-4-yl)-1,3,4-oxadiazol-2-thiol

• Published in: Asian Journal of Chemistry
• Main Author: Aziz-Ur-Rehman; Sattar A.; Abbasi M.A.; Siddiqui S.Z.; Raza M.A.; Ashraf M.; Nazir M.; Shah S.A.A.
• Format: Article
• Language: English
• Published: Chemical Publishing Co. 2018
• Online Access: https://www.scopus.com/inward/record.uri?eid=2-s2.0-85040132566&doi=10.14233%2fajchem.2018.20871&partnerID=40&md5=157c83646ac804918a4b607e79e83dff

Due to outstanding biological activities of 1,3,4-oxadiazole, a series of S-substituted derivatives of 5-[1-(4-tosyl)piperidin-4-yl]-1,3,4-oxadiazol-2-thiol (5a-f) was synthesized. The reaction of p-toluene sulfonyl chloride (a) with ethyl isonepacotate (b) produced ethyl 1-(4-tosyl)piperidin-4-carboxylate (1) which was successively converted to 1-(4-tosyl)piperidin-4-carbohydrazide (2) by hydrazine and 5-[1-(4-tosyl)piperidin-4-yl]-1,3,4-oxadiazol-2-thiol (3) by CS2 in the presence of KOH. The aimed compounds (5a-f) were synthesized by the reaction of compound 3 with different electrophiles in DMF using lithium hydride as catalyst. The structural confirmation was done by IR, 1H NMR & EI-MS spectral analysis. The synthesized compounds were screened against α-glucosidase enzyme and five Gram bacterial strains.