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Please use this identifier to cite or link to this item: http://142.54.178.187:9060/xmlui/handle/123456789/13128
Title: Synthesis of new antibacterial agents encompassing tosyl, piperidine, propanamide and 1,3,4-oxadiazole functionalities
Authors: Sattar, Almas
Rehman, Aziz-ur
Athar Abbasi, Muhammad
Zahra Siddiqui, Sabahat
Rasool, Shahid
Adnan Ali Shah, Syed
Keywords: 1,3,4-Oxadiazole
tosyl chloride
piperidine
ethyl isonipecotate
antibacterial activity
Issue Date: 1-Aug-2020
Publisher: Karachi:Pakistan Journal of Pharmaceutical Sciences, university of Karachi.
Citation: Sattar, A., Abbasi, M. A., Siddiqui, S. Z., Rasool, S., & Shah, S. A. A. (2020). Synthesis of new antibacterial agents encompassing tosyl, piperidine, propanamide and 1, 3, 4-oxadiazole functionalities. Pakistan journal of pharmaceutical sciences, 33(4), 1697-1706.
Abstract: A series of propanamide compounds 6a-l was derived by N-substitution reactions, encompassing tosyl, piperidine and 1,3,4-oxadiazole moieties. The intended array of compounds 6a-l was afforded by a series of five steps reaction scheme. 1-Tosylpiperidin-4-carboxylate (1) was synthesized by the reaction of tosyl chloride (a) with ethyl isonipecotate (b) under mild basic conditions. Compound 1 was subjected to nucleophillic substitution by hydrazine to synthesize 1-tosylpiperidin-4-carbohydrazide (2). The compound, 5-(1-tosylpiperidin-4-yl)-1,3,4-oxadiazole-2-thiol (3) was synthesized by intermolecular cyclization of compound 2 by CS2 under strong basic conditions. The target compounds, 6a-l, were finally synthesized from 3 by reacting with different electrophiles, 5a-l, in an aprotic polar solvent with sodium hydride as an activator. The different propanamoyl electrophiles, 5a-l, were synthesized by the reaction of different aromatic and aliphatic amines, 4a-l, with 3-bromopropionyl chloride under mild basic conditions. The structural elucidation was carried out using modern spectroscopic techniques including IR, 1H-NMR and EI-MS. The antibacterial potential of synthesized compounds was assessed against five bacterial strains. Compounds 6a, 6c, 6d, 6e and 6f were found to be potent antibacterial agents.
URI: http://142.54.178.187:9060/xmlui/handle/123456789/13128
ISSN: 1011-601X
Appears in Collections:Issue 4

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