Synthesis, Spectral Analysis and Biological Evaluation of Sulfamoyl and 1,3,4-oxadiazole Derivatives of 3-pipecoline. | [Pakistan Journal of Pharmaceutical Sciences • 2019]

Author(s):

1. Saira Jabeen Aslam: Department of Chemistry, Government College University, Lahore, Pakistan

2. Muhammad Athar Abbasi: Department of Chemistry, Government College University, Lahore, Pakistan

3. Sabahat Zahra Siddiqui: Department of Chemistry, Government College University, Lahore, Pakistan

4. Shahid Rasool: Department of Chemistry, Government College University, Lahore, Pakistan

5. Syed Adnan Ali Shah: Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), Universiti Teknologi MARA, Puncak Alam Campus, Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia; Faculty of Pharmacy, Universiti Teknologi MARA, Puncak Alam Campus, Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia

6. Aziz ur Rehman: Department of Chemistry, Government College University, Lahore, Pakistan

Abstract:

Heterocyclic chemistry is an important field of organic chemistry due to therapeutic potential. The minor modification in the structure of poly-functional compounds has great effect on therapeutic ability. In the presented research work, substituted 1,3,4-oxadiazole derivatives, 8a-p, have been synthesized by the reaction of 1-(4bromomethylbenzenesulfonyl)-3-methylpiperidine (7) and 5-substituted-1,3,4-oxadiazole-2-thiol (4a-p). The 5substituted-1,3,4-oxadiazole-2-thiol were synthesized by converting carboxylic acids correspondingly into esters, hydrazides and oxadiazoles. Secondly the electrophile, 1-(4-Bromomethylbenzenesulfonyl)-3-methylpiperidine (7), was prepared by the reaction of 3-methylpiperidine with 4-bromomethylbenzenesulfonyl chloride in the presence of water and Na2CO3 under pH of 9-10. The compounds were structurally corroborated through spectroscopic data analysis of IR, EI-MS and 1H-NMR. The screening for antibacterial activity revealed the compounds to be moderate to excellent inhibitors against bacteria under study. Anti-enzymatic activity was assessed against urease enzyme and 1-{[4-({[5-(3nitrophenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}methyl)phenyl]sulfonyl}-3-methylpiperidine (8d) was the most active one.

Page(s): 987-996

DOI: DOI not available

Published: Journal: Pakistan Journal of Pharmaceutical Sciences, Volume: 32, Issue: 3, Year: 2019

Keywords:

antiurease activity

References:

References are not available for this document.

Citations

Citations are not available for this document.

Citations

Downloads

Views