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- Title
Synthesis, spectral analysis and biological evaluation of sulfamoyl and 1,3,4-oxadiazole derivatives of 3-pipecoline.
- Authors
Aziz-ur-Rehman; Aslam, Saira Jabeen; Abbasi, Muhammad Athar; Siddiqui, Sabahat Zahra; Rasool, Shahid; Ali Shah, Syed Adnan
- 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-(4- bromomethylbenzenesulfonyl)-3-methylpiperidine (7) and 5-substituted-1,3,4-oxadiazole-2-thiol (4a-p). The 5-substituted-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-(3-nitrophenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}methyl)phenyl]sulfonyl}-3-methylpiperidine (8d) was the most active one.
- Subjects
HETEROCYCLIC chemistry; CARBOXYLIC acids; ESTERS; ORGANIC chemistry; DATA analysis; EVALUATION
- Publication
Pakistan Journal of Pharmaceutical Sciences, 2019, Vol 32, Issue 3, p987
- ISSN
1011-601X
- Publication type
Article