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Synthesis and biological evaluation of some heterocyclic scaffolds based on the multifunctional N ‐(4‐acetylphenyl)‐2‐chloroacetamide
Author(s) -
AbdelLatif Ehab,
Fahad Mustafa M.,
ElDemerdash Amr,
Ismail Mohamed A.
Publication year - 2020
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.4012
Subject(s) - chemistry , semicarbazone , phenacyl bromide , sodium ethoxide , derivative (finance) , reagent , phenylhydrazine , formylation , ethyl bromoacetate , medicinal chemistry , antibacterial activity , sodium sulfide , thiazoline , organic chemistry , biology , bacteria , ethanol , financial economics , economics , genetics , catalysis
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 (POCl 3 /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.