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Short Paper | Regular issue | Vol 100, No. 11, 2020, pp.1883-1901
Published online, 21st August, 2020
DOI: 10.3987/COM-20-14298
Synthesis and Antibacterial Survey of Some New Pyridine-Based Heterocycles

Ebrahim Abdel-Galil, Moged A. Berghot, Alshimaa I. Zaki, and Ehab Abdel-Latif*

*Department of Chemistry, Faculty of Science, Mansoura University, Mansoura, Egypt

Abstract

Treatment of ethyl 2-((3-cyano-4,6-dimethylpyridin-2-yl)thio)acetate (4) with hydrazine hydrate furnished 2-((3-cyano-4,6-dimethylpyridin-2-yl)thio)-acetohydrazide (5) which underwent condensation with five benzaldehydes to afford the corresponding N'-arylidene-2-((3-cyano-4,6-dimethylpyridin-2-yl)thio)-acetohydrazides 6a-e. The reaction of hydrazide 5 with ethyl acetoacetate yielded the expected 2-((2-(3-methyl-5-oxo-pyrazolyl)-2-oxoethyl)thio)nicotinonitrile derivative 7 which diazo-coupled with different diazonium chlorides to furnish the corresponding 2-(4-(2-arylhydrazono)pyrazolyl)-2-oxoethyl)thio)nicotinonitriles 8a-c. In addition, the nucleophilic substitution of chlorine from 2-chloroacetamide derivative 16 by various types of nucleophiles (salicylaldehyde, ethyl thioglycolate, 2-mercaptobenzoxazole, ammonium thiocyanate and/or malononitrile) was investigated. In general, all synthesized pyridine scaffolds revealed better activity against the Gram-positive bacterium (Bacillus subtilis) rather than the Gram-negative bacterium (Escherichia coli).