Tiacrilast, Ro-22-3747/007(Na salt), Ro-22-3747/000, Ro-22-3747
硫克司特Chemical Name: (E)-3-[(6-Methylthio)-4-oxo-3(4H)-quinazolinyl]-2-propenoic acid; (E)-6-(Methylthio)-4-oxo-3(4H)-uinazolineacrylic acid
CAS No. 78299-53-3, 111868-63-4 (Na salt, monohydrate)
项目整合开发状态: Phase II
项目研究机构: Roche (Originator)
合成路线:The cyclization of methyl-5-(methylthio)anthranilate (I) with formamide (II) by heating at 190 C gives 6-(methylthio)-4(3H)-quinazolinone (III),which is condensed with methyl 3-chloroacrylate (IV) by means of NaH yielding methyl 3-[6-(methylthio)-4-oxo-4H-quinazolin-3-yl]-2-propenoate (V).Finally,this compound is hydrolyzed with refluxing 6N HCl.The same procedure of synthesis can also be performed from 5-(methylthio)anthranilic acid instead of methyl 5-(methylthio)anthranilate (I).
📌 参考资料/链接：
参考文献标题:Trans-3-(4-oxo-4H-quinazolin-3-yl)-2-propenoic acid derivatives
文献作者:Lemahieu,R.A.; Nason,W.C.(Hoffmann-La Roche,Inc.)
参考来源:EP 0023594; JP 8125167; US 4281127
📄 详细内容
合成路线:The cyclization of methyl-5-(methylthio)anthranilate (I) with formamide (II) by heating at 190 C gives 6-(methylthio)-4(3H)-quinazolinone (III),which is condensed with methyl 3-chloroacrylate (IV) by means of NaH yielding methyl 3-[6-(methylthio)-4-oxo-4H-quinazolin-3-yl]-2-propenoate (V).Finally,this compound is hydrolyzed with refluxing 6N HCl.The same procedure of synthesis can also be performed from 5-(methylthio)anthranilic acid instead of methyl 5-(methylthio)anthranilate (I).
参考文献标题:Tiacrilast
文献作者:Serradell,M.N.; Castar,J.; Chu,S.S.
参考来源:Drugs Fut 1985,10(2),131
合成路线:The cyclization of methyl-5-(methylthio)anthranilate (I) with formamide (II) by heating at 190 C gives 6-(methylthio)-4(3H)-quinazolinone (III),which is condensed with methyl 3-chloroacrylate (IV) by means of NaH yielding methyl 3-[6-(methylthio)-4-oxo-4H-quinazolin-3-yl]-2-propenoate (V).Finally,this compound is hydrolyzed with refluxing 6N HCl.The same procedure of synthesis can also be performed from 5-(methylthio)anthranilic acid instead of methyl 5-(methylthio)anthranilate (I).
参考文献标题:(E)-3-(4-Oxo-4H-quinazolin-3-yl=-2-propenoic acids,a new series of antiallergy agents
文献作者:LeMahieu,R.A.; Carson,M.; Nason,W.C.; Parrish,D.R.; Welton,A.F.; Baruth,H.W.; Yaremko,B.
参考来源:J Med Chem 1983,26(3),420-423
产品链接: CAS No. 78299-53-3›› 产品链接: CAS No.111868-63-4››