Structure–activity relationship and in silico study of unique bi-heterocycles: 5-[(2-amino-1,3-thiazol-4-yl)methyl]-1,3,4-oxadiazole-2-thiol derivatives

Muhammad Athar Abbasi, Muhammad Shahid Ramzan, Aziz Ur Rehman, Sabhat Zahra Siddiqui, Mubashir Hassan, Hussain Raza, Syed Adnan Ali Shah, Bushra Mirza, Sung-Yum Seo

Abstract


This paper presents the synthesis of some unique bi-heterocyclic hyb­rid molecules with a thiazole and an oxadiazole ring. The synthesis was ini­tiated by the conversion of ethyl 2-(2-amino-1,3-thiazol-4-yl)acetate (1) to the corres­pond­ing 2-(2-amino-1,3-thiazol-4-yl)acetohydrazide (2) by the reaction with hydra­zine hydrate in methanol. The treatment of the acid hydrazide, 2, with carbon disulfide gave the bi-heterocyclic nucleophile, 5-[(2-amino-1,3-
-thiazol-4-yl)­methyl]-1,3,4-oxadiazole-2-thiol (3). Finally, the target com­pounds, 5ao, were synthesized by stirring the nucleophile 3 with different electrophiles, 4ao, in DMF using LiH as a base and an activator. The struc­tures of the newly syn­thesized molecules were confirmed through spectro­scopic techniques, such as IR, EI-MS, 1H-NMR and 13C-NMR. The structure–
–activity relationship of all these bi-heterocycles was established by evaluating them against four enzymes, namely, acetylcholinesterase, butyrylcholines­ter­ase, urease and a-glucosidase, followed by their in silico study. Moreover, their cytotoxicity was also profiled by killing data of brine shrimps at various concentrations.


Keywords


1,3-thiazole; 1,3,4-oxadiazole; acetylcholinesterase; butyrylchol¬inesterase; urease; glucosidase; molecular docking; brine shrimps

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DOI: https://doi.org/10.2298/JSC180203019A

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