Journal
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
Volume 45, Issue 5, Pages 1976-1981Publisher
ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
DOI: 10.1016/j.ejmech.2010.01.042
Keywords
6-Amino-2-mercaptopyrimidin-4(3H)-one; 2,3-Dichloroquinoxaline; Pyrimido[2 ',1 ':2,3]thiazolo[4,5-b]quinoxaline; Anti-inflammatory activities; Analgesic activities
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Treatment of 6-aminothiouracil (1) with 2,3-dichloroquinoxaline (2) in ethanol/TEA afforded 6-amino-2-(3-chloroquinoxalin-2-ylthio)pyrimidin-4(3H)-one (3), which was refluxed in DMF to give 2-aminopyrimidoi[2',1':2,3]thiazolo[4,5-b]quinoxaline-4-one (4). Compound 4 was utilized as a key intermediate for the synthesis of a new pyrimido[2',1':2,3]thiazolo[4,5-b]quinoxaline derivatives 5-14 via the reaction with 2-chlorobenzaldehyde, 2-chlorocyclohex-1-enecarbaldehyde, 2-chlorobenzoic acid, 2,4-dichlorbenzoic acid, 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde, 2-chloro-4,6-dimethylnicotinonitrile, a,alpha,beta-unsaturated ketones and isonicotinaldehyde, respectively. The chemical structures of the newly synthesized compounds were characterized by IR, NMR and mass spectral analysis. These compounds were also screened for their analgesic and anti-inflammatory activities. Some of these compounds (3, 4,9,10 and 12-14) exhibited promising activities. (C) 2010 Elsevier Masson SAS. All rights reserved.
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