Synthesis and Biological Activity of 2,3-Bis-(2-Oxoylidene)-1,2,3,4-Tetrahydroquinoxalines

Autor:	S. S. Zykova, R. R. Makhmudov, O. G. Karmanova, T. F. Odegova
Rok vydání:	2015
Předmět:	Pharmacology Antioxidant Low toxicity Chemistry DPPH medicine.medical_treatment Biological activity medicine.disease_cause Acute toxicity chemistry.chemical_compound Drug Discovery medicine Organic chemistry Trolox Escherichia coli Diethyl oxalate Nuclear chemistry
Zdroj:	Pharmaceutical Chemistry Journal. 48:640-645
ISSN:	1573-9031 0091-150X
DOI:	10.1007/s11094-015-1163-6
Popis:	Condensation of alkylmethylketones with diethyl oxalate and 1,2-diaminobenzene yielded 2,3-bis-(2-oxoylidene)-1,2,3,4-tetrahydroquinoxalines (II – IV). Four isomeric species were identified using spectral methods. Structural features of the synthesized compounds were discussed. The biological activity of the obtained compounds was investigated. It was observed that the synthesized compounds had low toxicity. It was found that (1Z,1′Z)-1,1′-(1,4-dihydroquinoxaline-2,3-diylidene)dibutan-2-one (II) exhibited antinociceptive activity that was greater than that of metamizole sodium. The antioxidant activity in an Escherichia coli BW 25113 oxidation resistance model in the presence of H2O2 solution (3 mM) was also most pronounced for II whereas V had pro-oxidant activity. The compounds showed high antiradical activity for diphenylpicrylhydrazyl (DPPH) binding that was comparable with that of trolox.
Databáze:	OpenAIRE
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