Z-335
盐2-[2-(4-氯苯磺酰氨基甲基)铟烷-5-基]乙酸钠Chemical Name: 2-[2-(4-Chlorophenylsulfonamidomethyl)indan-5-yl]acetic acid sodium salt
CAS No. 146731-14-8, 146737-36-2 (free acid)
项目整合开发状态: Phase II
项目研究机构: Zeria (Originator)
合成路线:Curtius rearrangement of indanylacetic acid (I) using diphenylphosphoryl azide (DPPA) in the presence of benzyl alcohol afforded benzyl carbamate (II).Hydrogenolytic deprotection of (II) in the presence of palladium catalyst then provided amine (III),which was condensed with 4-chlorobenzenesulfonyl chloride (IV) to give sulfonamide (V).Subsequent Friedel Crafts reaction of (V) with ethyl a-chloro-a-(methylsulfanyl)acetate (VI) and SnCl4 furnished sulfide (VII),from which the methylthio group was removed by reductive treatment with Zn dust in AcOH yielding (VIII).Finally,alkaline hydrolysis of the indanylacetic ester (VIII) provided the title carboxylic acid,isolated as the corresponding sodium salt.
📌 参考资料/链接:
参考文献标题:Synthesis and thromboxane A2 antagonistic activity of indane derivatives
文献作者:Shinozaki,K.; Sato,H.; Iwakuma,T.; Sato,R.; Kurimoto,T.; Yoshida,K.
参考来源:Bioorg Med Chem Lett 1999,9(3),401