Tiprostanide, EMD-33290
Chemical Name: [1S-[1alpha,2beta(R*),3alpha]]-3-Hydroxy-2-(2-hydroxy-2-methylheptylsulafanyl)-5-oxocyclopentaneheptanoic acid 4-(benzamido)phenyl ester; (1S,2R,3R)-3-Hydroxy-2-[2(S)-hydroxy-2-methylheptylsulfanyl]-5-oxocyclopentaneheptanoic acid 4-(benzamido)phenyl este
项目整合开发状态: Preclinical
项目研究机构: Merck KGaA (Originator)
合成路线:EMD-33.290 can be prepared by conjugate addition of 2-hydroxy-2-methylheptanethiol (II) to 3-hydroxy-5-oxocyclopentenylheptanoic acid p-benzamidophenyl ester (I) to give rise to the title compound as the main product (III) along with two epimers.Isolation of pure EMD-33.290 can be achieved by medium-pressure chromatography.An alternative synthesis utilizing the Roberts' approach has been reported to give the appropriate PGF2alpha analogue,which is converted to EMD-33.290 by selective oxidation.
📌 参考资料/链接：
参考文献标题:EMD-33,290
文献作者:Koch,H.
参考来源:Drugs Fut 1983,8(7),585
📄 详细内容
合成路线:EMD-33.290 can be prepared by conjugate addition of 2-hydroxy-2-methylheptanethiol (II) to 3-hydroxy-5-oxocyclopentenylheptanoic acid p-benzamidophenyl ester (I) to give rise to the title compound as the main product (III) along with two epimers.Isolation of pure EMD-33.290 can be achieved by medium-pressure chromatography.An alternative synthesis utilizing the Roberts' approach has been reported to give the appropriate PGF2alpha analogue,which is converted to EMD-33.290 by selective oxidation.
参考文献标题:Synthesis of EMD-33290,a new oral blood pressure lowering prostaglandin E2 analog
文献作者:Radunz,H.E.; Riefling,B.F.
参考来源:Acta Ther (Belg) 1980,6(4),58