新产品编号:282105
Chemical Name: 4-[3-(4-Fluorophenyl)-2-oxo-2,3-dihydrooxazol-4-yl]benzenesulfonamide
CAS No. 197240-09-8
项目整合开发状态: Preclinical
项目研究机构: Almirall Prodesfarma (Originator)
合成路线:The synthesis of the title compound has been reported by two related procedures.Cyclization of phenacyl N-(4-fluorophenyl)carbamate (I) in boiling HOAc gave rise to oxazolone (II).Chlorosulfonation of (II),followed by treatment of the resulting sulfonyl chloride (III) with ammonia,yielded the title sulfonamide.
📌 参考资料/链接：
参考文献标题:2-(3H)-Oxazolone derivs.and their use as COX-2 inhibitors
文献作者:Puig Duran,C.; Pujol Noguera,F.; Fernandez Forner,D.(Almirall Prodesfarma,SA)
参考来源:EP 0888316; ES 2125161; JP 2000506876; WO 9734882
📄 详细内容
合成路线:In an alternative procedure,sodium 4-acetylbenzenesulfonate (IV) was refluxed with POCl3 and subsequently treated with dibenzylamine to afford sulfonamide (V).Bromination of (V) in chloroform yielded the bromo ketone (VI),which was hydrolyzed to phenacyl alcohol (VII) by treatment with ethanolic betaine,followed by aqueous NaHCO3.Addition of 4-fluorophenyl isocyanate (VIII) to (VII) and then cyclization in refluxing HOAc yielded the oxazolone (IX).Final debenzylation was achieved with concentrated H2SO4 to give the target sulfonamide.
参考文献标题:Synthesis and biological evaluation of 3,4-diaryloxazolones: A new class of orally active cyclooxygenase-2 inhibitors
文献作者:Puig,C.; Crespo,M.I.; Godessart,N.; Feixas,J.; Ibarzo,J.; Jimenez,J.M.; Soca,L.; Cardelus,I.; Heredia,A.; Miralpeix,M.; Puig,J.; Beleta,J.; Huerta,J.M.; Lopez,M.; Segarra,V.; Ryder,H.; Palacios,J.M.
参考来源:J Med Chem 2000,43(2),214