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Please use this identifier to cite or link to this item: http://142.54.178.187:9060/xmlui/handle/123456789/14936
Title: Synthesis, spectral analysis and biological evaluation of sulfamoyl and 1,3,4-oxadiazole derivatives of 3-pipecoline
Authors: Rehman, Aziz-ur
Aslam, Saira Jabeen
Abbasi, Muhammad Athar
Siddiqui, Sabahat Zahra
Rasool, Shahid
Shah, Syed Adnan Ali
Keywords: 1,3,4-Oxadiazole
3-methylpiperidine
antibacterial activity
anti-urease activity
sulfonamide
Issue Date: 15-May-2019
Publisher: Karachi: Faculty of Pharmacy & Pharmaceutical Sciences University of Karachi
Citation: Siddiqui, S. Z., Rasool, S., & Shah, S. A. A. (2019). Synthesis, spectral analysis and biological evaluation of sulfamoyl and 1, 3, 4-oxadiazole derivatives of 3-pipecoline. Pak. J. Pharm. Sci, 32(3), 987-996.
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 1 H-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.
URI: http://142.54.178.187:9060/xmlui/handle/123456789/14936
ISSN: 1011-601X
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