Photochemistry Department (Heterocyclic Unit), National Research Center, Dokki, Giza, Egypt.
Eur J Med Chem. 2010 May;45(5):1976-81. doi: 10.1016/j.ejmech.2010.01.042. Epub 2010 Jan 28.
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-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 5-14via the reaction with 2-chlorobenzaldehyde, 2-chlorocyclohex-1-enecarbaldehyde, 2-chlorobenzoic acid, 2,4-dichlorobenzoic acid, 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde, 2-chloro-4,6-dimethylnicotinonitrile, 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.
用 2,3-二氯喹喔啉（2）处理 6-氨基硫代尿嘧啶（1）在乙醇/TEA 中得到 6-氨基-2-(3-氯喹喔啉-2-基硫代)嘧啶-4(3H)-酮（3），将其在 DMF 中回流得到 2-氨基嘧啶并[2',1':2,3]噻唑并[4,5-b]喹喔啉-4-酮（4）。化合物 4 被用作合成新型嘧啶并[2',1':2,3]噻唑并[4,5-b]喹喔啉衍生物 5-14 的关键中间体，通过与 2-氯苯甲醛、2-氯环己-1-烯甲醛、2-氯苯甲酸、2,4-二氯苯甲酸、5-氯-3-甲基-1-苯基-1H-吡唑-4-甲醛、2-氯-4,6-二甲基烟腈、α,β-不饱和酮和异烟醛反应得到。新合成的化合物的化学结构通过 IR、NMR 和质谱分析进行了表征。这些化合物还进行了镇痛和抗炎活性筛选。其中一些化合物（3、4、9、10 和 12-14）表现出有希望的活性。
