Affiliations 

  • 1 Department of Chemistry, Government College University, Lahore, Pakistan
  • 2 Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad, Pakistan
  • 3 Department of Chemistry, University of Education, DGK Campus, Dera Ghazi Khan, Pakistan
  • 4 Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur, Pakistan
  • 5 Faculty of Pharmacy and Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), University Teknologi MARA, Puncak Alam Campus, Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia
Pak J Pharm Sci, 2018 Jul;31(4(Supplementary)):1501-1510.
PMID: 30058542

Abstract

N-(Substituted)-5-(1-(4-methoxyphenylsulfonyl)piperidin-4-yl)-4H-1,2,4-triazol-3-ylthio) acetamide were synthesized by following conventional as well as microwave assisted protocol through five consecutive steps under the impact of various reaction conditions to control the reaction time and the yield of product. Starting from 4-methoxybenzenesulfonyl chloride and ethyl isonipecotate, product 3 was obtained which was converted into product 4 by treating with hydrazine hydrate. In step 3, the product 4 was refluxed with methyl isothiocyanate and KOH to yield compound 5 which was finally treated with variety of N-substituted acetamides to yield an array of different new compounds (8a-k). These synthesized compounds were evaluated for their inhibition potential against bovine carbonic anhydrase (bCA-II), acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes. Compound 8g demonstrated good activity against bCA-II, AChE and BChE with IC50 values of 8.69 ± 0.38 μM, 11.87±0.19 μM and 26.01±0.55 μM respectively. SAR studies assisted with molecular docking were carried out to explore the mode of binding of the compounds against the studied enzymes.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.