Wy-44221
Chemical Name: (S,S)-1-(2-Methyl-3-sulfanyl-1-oxopropyl)-2,3-dihydro-1H-indole-2-carboxylic acid; (S,S)-1-(2-Methyl-3-sulfanyl-1-oxopropyl)indoline-2-carboxylic acid; (S,S)-1-(2-Methyl-3-sulfanylpropionyl)indoline-2-carboxylic acid; (S,S)-1-(3-Mercaptoisobutyryl)indoline-2-carboxylic acid
CAS No. 78779-29-0 ((-)-enantiomer)
项目整合开发状态: Biological Testing
项目研究机构: Wyeth Pharmaceuticals (Originator)
合成路线:This compound can be obtained by several related ways:1) The hydrolysis of ethyl indoline 2 carboxylate (I) with KOH in aqueous DMSO gives indoline 2-carboxylic acid (II),which is acylated with 3-(benzoylthio)-2-methylpropanoyl chloride (III) in methylene chloride yielding 1-[3-(benzoylthio)-2-methyl-1-oxopropyl]indoline-2-carboxylic acid (IV).Finally,this compound is debenzoylated by treatment with 2-methoxyethylamine (A).2) The acylation of (I) with methacryloyl chloride (V) by means of triethylamine in ether yields ethyl 1-methacryloylindoline-2-carboxylate (VI),which is hydrolyzed with KOH in aqueous DMSO affording 1-methacryloylindoline-2-carboxylic acid (VII).Finally,this compound is treated with thiobenzoic acid (VIII) and 4-dimethylaminopyridine in acetone to give (IV),previously synthesized.3) The acylation of acid (II) with (V) as before also gives (VII).
📌 参考资料/链接：
参考文献标题:WY-44221
文献作者:Serradell,M.N.; Castar,J.; Blancafort,P.
参考来源:Drugs Fut 1983,8(11),953
📄 详细内容
合成路线:This compound can be obtained by several related ways:1) The hydrolysis of ethyl indoline 2 carboxylate (I) with KOH in aqueous DMSO gives indoline 2-carboxylic acid (II),which is acylated with 3-(benzoylthio)-2-methylpropanoyl chloride (III) in methylene chloride yielding 1-[3-(benzoylthio)-2-methyl-1-oxopropyl]indoline-2-carboxylic acid (IV).Finally,this compound is debenzoylated by treatment with 2-methoxyethylamine (A).2) The acylation of (I) with methacryloyl chloride (V) by means of triethylamine in ether yields ethyl 1-methacryloylindoline-2-carboxylate (VI),which is hydrolyzed with KOH in aqueous DMSO affording 1-methacryloylindoline-2-carboxylic acid (VII).Finally,this compound is treated with thiobenzoic acid (VIII) and 4-dimethylaminopyridine in acetone to give (IV),previously synthesized.3) The acylation of acid (II) with (V) as before also gives (VII).
参考文献标题:Mercaptopropanoyl)indoline-2-carboxylic acids and related compounds as potent angiotensin converting enzyme inhibitors and antihypertensive agents
文献作者:Kim,D.H.; Guinosso,C.J.; Buzby,G.C.Jr.; Herbst,D.R.; McCaully,R.J.; Wicks,T.C.; Wendt,R.L.
参考来源:J Med Chem 1983,26(3),394-403
合成路线:The esterification of indoline-2-carboxylic acid (I) with ethanol HCl gives the corresponding ethyl ester (II),which is acylated with 3-(benzoylthio)-2-methylpropionyl chloride (III) by means of K2CO3 in methylene chloride yielding ethyl N-[3-(benzoylthio)-2-methylpropionyl]indoline-2-carboxylate (IV).The deprotection of (IV) with hydrazine in the same solvent affords ethyl N-(3-mercapto-2-methylpropionyl)indoline-2-carboxylate (V),which is finally saponified with KOH in methanol water.
参考文献标题:Angiotensin converting enzyme inhibitors: N-Substituted monocyclic and bibyvlic amino acid deivatives
文献作者:Stanton,J.L.; Gruenfeld,N.; Babiarz,J.E.; Ackerman,M.H.; Friedmann,R.C.; Yuan,A.M.; Macchia,W.
参考来源:J Med Chem 1983,26(9),1267-77
产品链接: CAS No. 78779-29-0››