N-(5-Methyl-1,3-Thiazol-2-yl)-2-{[5-((Un)Substituted- Phenyl)1,3,4-Oxadiazol-2-yl]Sulfanyl}acetamides. Unique Biheterocycles as Promising Therapeutic Agents

• Published in: Russian Journal of Bioorganic Chemistry
• Main Author: Abbasi M.A.; Ramzan M.S.; Aziz-ur-Rehman; Siddiqui S.Z.; Shah S.A.A.; Hassan M.; Seo S.-Y.; Ashraf M.; Mirza B.; Ismail H.
• Format: Article
• Language: English
• Published: Pleiades Publishing 2018
• Online Access: https://www.scopus.com/inward/record.uri?eid=2-s2.0-85061985685&doi=10.1134%2fS106816201806002X&partnerID=40&md5=edcb893473caea547fccb2ed25ecac83

An electrophile, 2-bromo-N-(5-methyl-1,3-thiazol-2-yl)acetamide, was synthesized by the reaction of 5-methyl-1,3-thiazol-2-amine and bromoacetyl bromide in an aqueous medium. In a parallel scheme, a series of (un)substituted benzoic acids was converted sequentially into respective esters, acid hydrazides, and then into 1,3,4-oxadiazole heterocyclic cores. The electrophile was coupled with the aforementioned 1,3,4-oxadiazoles to obtain the targeted bi-heterocyles. Structural analysis of the synthesized compounds was performed by IR, EI-MS, 1 H NMR, and 13 C NMR. The enzyme inhibition study of these molecules was carried out against four enzymes, namely, acetylcholinesterase, butyrylcholinesterase, α-glucosidase, and urease. The interactions of these compounds with respective enzymes were recognized by their in silico study. Moreover, their cytotoxicity was also determined to find out their utility as possible therapeutic agents. © 2018, Pleiades Publishing, Ltd.