Z-321
Chemical Name: 1-[N-(2-Indanylacetyl)-4-thia-L-prolyl]pyrrolidine; 1-[3-(2-Indanylacetyl)thiazolidin-4(R)-ylcarbonyl]pyrrolidine
CAS No. 130849-58-0
项目整合开发状态: Phase I
项目研究机构: Zeria (Originator)
合成路线:Coupling of indanylacetic acid (IV) with L-thioproline ethyl ester (V) by means of EDC gave amide (VI).Subsequent saponification of the ethyl ester group of (VI) furnished (indanylacetyl)thioproline (VII).The title compound was finally obtained by coupling of acid (VII) with pyrrolidine (VIII).
📌 参考资料/链接：
参考文献标题:Condensed benzene deriv.
文献作者:Aotsuka,T.; Torizuka,M.; Soeda,M.; Ogura,K.; Tanaka,Y.; Kato,H.; Nakata,N.; Miura,N.; Morita,H.(Zeria Pharmaceutical Co.,Ltd.)
参考来源:AU 8945914; EP 0372484; JP 1990262557; US 5028604
📄 详细内容
合成路线:Alternatively,the title compound was prepared by condensation between indanylacetic acid (IV) and thioprolylpyrrolidine (XI) either using EDC as the coupling reagent or via activation as the mixed anhydride (X) with pivaloyl chloride (IX) and triethylamine.
参考文献标题:Cholinesterase activator
文献作者:Tanaka,Y.; Kobayashi,N.; Nakata,N.; Yamaguchi,I.; Mori,T.(Zeria Pharmaceutical Co.,Ltd.)
参考来源:EP 0754454; JP 1995228529; US 6017929; WO 9522326
合成路线:Aldol condensation between 1-indanone (I) and glyoxylic acid (II) in the presence of H2SO4 afforded keto acid (III).Catalytic hydrogenation of (III) over Pd/C furnished 2-indanylacetic acid (IV).
合成路线:Alternatively,the title compound was prepared by condensation between indanylacetic acid (IV) and thioprolylpyrrolidine (XI) either using EDC as the coupling reagent or via activation as the mixed anhydride (X) with pivaloyl chloride (IX) and triethylamine.
参考文献标题:New potent prolyl endopeptidase inhibitors: Synthesis and structure-activity relationships of indan and tetralin derivatives and their analogues
文献作者:Tanaka,Y.; Niwa,S.; Nishioka,H.; Yamanaka,T.; Torizuka,M.; Yoshinaga,K.; Kobayashi,N.; Ikeda,Y.; Arai,H.
参考来源:J Med Chem 1994,37(13),2071
产品链接: CAS No. 130849-58-0››