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Synthesis of some new pyrimido[2′,1′:2,3]thiazolo[4,5- b]quinoxaline derivatives as anti-inflammatory and analgesic agents
Ist Teil von
European journal of medicinal chemistry, 2010-05, Vol.45 (5), p.1976-1981
Ort / Verlag
Kidlington: Elsevier Masson SAS
Erscheinungsjahr
2010
Quelle
MEDLINE
Beschreibungen/Notizen
Treatment of 6-aminothiouracil (
1) with 2,3-dichloroquinoxaline (
2) in ethanol/TEA afforded 6-amino-2-(3-chloroquinoxalin-2-ylthio)pyrimidin-4(3
H)-one (
3), which was refluxed in DMF to give 2-aminopyrimido[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-dichlorobenzoic acid, 5-chloro-3-methyl-1-phenyl-1
H-pyrazole-4-carbaldehyde, 2-chloro-4,6-dimethylnicotinonitrile, α,β-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.
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