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

Authors

  • Muhammad Athar Abbasi Department of Chemistry, Government College University, Lahore-54000 and College of Natural Sciences, Department of Biological Sciences, Kongju National University, Gongju, 32588 South Korea
  • Muhammad Shahid Ramzan Department of Chemistry, Government College University, Lahore-54000
  • Aziz Ur Rehman Department of Chemistry, Government College University, Lahore-54000
  • Sabhat Zahra Siddiqui Department of Chemistry, Government College University, Lahore-54000
  • Mubashir Hassan College of Natural Sciences, Department of Biological Sciences, Kongju National University, Gongju, 32588
  • Hussain Raza College of Natural Sciences, Department of Biological Sciences, Kongju National University, Gongju, 32588
  • Syed Adnan Ali Shah Faculty of Pharmacy and Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), Level 9, FF3, Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan
  • Bushra Mirza Department of Biochemistry, Quaid-i-Azam University, Islamabad, 45320
  • Sung-Yum Seo College of Natural Sciences, Department of Biological Sciences, Kongju National University, Gongju, 32588

DOI:

https://doi.org/10.2298/JSC180203019A

Keywords:

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

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.

Author Biographies

Muhammad Athar Abbasi, Department of Chemistry, Government College University, Lahore-54000 and College of Natural Sciences, Department of Biological Sciences, Kongju National University, Gongju, 32588 South Korea

Associate Professor

Muhammad Shahid Ramzan, Department of Chemistry, Government College University, Lahore-54000

PhD Scholar, Department of Chemistry,

Aziz Ur Rehman, Department of Chemistry, Government College University, Lahore-54000

Government College University, Lahore-54000

Hussain Raza, College of Natural Sciences, Department of Biological Sciences, Kongju National University, Gongju, 32588

Assiatant Professor

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Published

2019-07-29

How to Cite

[1]
M. A. Abbasi, “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”, J. Serb. Chem. Soc., vol. 84, no. 7, pp. 649–661, Jul. 2019.

Issue

Section

Organic Chemistry