Synthesis and biological evaluation of some heterocyclic scaffolds based on the multifunctional N-(4-acetylphenyl)-2-chloroacetamide

Abdel-Latif, Ehab, Fahad, Mustafa M., El-Demerdash, Amr ORCID: https://orcid.org/0000-0001-6459-2955 and Ismail, Mohamed A. (2020) Synthesis and biological evaluation of some heterocyclic scaffolds based on the multifunctional N-(4-acetylphenyl)-2-chloroacetamide. Journal of Heterocyclic Chemistry, 57 (8). pp. 3071-3081. ISSN 0022-152X

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Abstract

The chloroacetamide derivative, 1, was used as a versatile precursor for the synthesis of various types of N-aryl-2-(benzothiazol-2-ylthio)acetamide derivatives. The reaction of 1 with 2-mercaptobenzothiazole followed by condensation reaction of the produced sulfide with phenylhydrazine, 2-cyanoacetohydrazide, and/or thiosemicarbazide furnished the conforming condensation products, 4, 7, and 10, respectively. Treatment of the phenylhydrazone product, 4, with Vilsmeier formylation reagent (POCl3/DMF) yielded the corresponding 4-formylpyrazole derivative, 5. The thiosemicarbazone product, 10, was reacted with ethyl bromoacetate to furnish the thiazolin-4-one derivative, 11. The substitution reactions of chloroacetamide derivative, 1, with 2-mercapto-4,6-dimethylnicotinonitrile and 6-amino-2-mercaptopyrimidin-4-ol, were explored to identify the sulfide products, 14 and 17. Cyclization of 14 into its corresponding thieno[2,3-b]pyridine compound, 15, was performed using sodium ethoxide. The thiosemicarbazone, 10, and sulfide derivative, 14, were found to be the most potent antibacterial compounds against Escherichia coli and Staphylococcus aureus, exhibiting growth inhibitory activities of 80.8% and 91.7%, respectively. Moreover, the thiosemicarbazone, 10, displayed the most significant antioxidant activity with inhibitory activity of 82.6%, which comes close to the antioxidant activity of L-ascorbic acid.

Item Type:	Article
Additional Information:	Publisher Copyright: © 2020 Wiley Periodicals LLC.
Uncontrolled Keywords:	organic chemistry ,/dk/atira/pure/subjectarea/asjc/1600/1605
Faculty \ School:	Faculty of Science > School of Pharmacy (former - to 2024)
Related URLs:	http://www.scopus.com/inward/record.url?...
Depositing User:	LivePure Connector
Date Deposited:	05 Aug 2024 11:32
Last Modified:	25 Sep 2024 17:59
URI:	https://ueaeprints.uea.ac.uk/id/eprint/96134
DOI:	10.1002/jhet.4012

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