长春花生物碱及相关化合物的合成。第84部分。一些具有心血管活性的长春花生物碱的磺酰胺衍生物。

Synthesis of vinca alkaloids and related compounds. Part 84. Sulfonamide derivatives of some vinca alkaloids with cardiovascular activity.

作者信息

Moldvai I, Temesvári-Major E, Szántay C, Tóth G, Kárpáti E, Szántay C

机构信息

Central Research Institute for Chemistry, Hungarian Academy of Sciences, Budapest, Hungary.

出版信息

Arch Pharm (Weinheim). 1997 Jun;330(6):190-8. doi: 10.1002/ardp.19973300607.

DOI:10.1002/ardp.19973300607

PMID:9264244

Abstract

(+)-Vincamine (1) and (+)-vinpocetine (2) were chlorosulfonylated and the resulting sulfonyl chloride isomers (3-6) were transformed into sulfonamides (7-10). The ester group of sulfonamides was modified by selective hydrolysis and transesterification. Apovincaminol derivatives (14-16) were also prepared by reduction. In addition to the known cerebrovascular effects of the unsubstituted compounds (1,2) sulfonamides also show a significant peripheral vasodilator effect.

摘要

（+）-长春胺（1）和（+）-长春西汀（2）进行氯磺酰化反应，所得的磺酰氯异构体（3 - 6）转化为磺酰胺（7 - 10）。通过选择性水解和酯交换反应对磺酰胺的酯基进行修饰。还通过还原反应制备了阿朴长春胺醇衍生物（14 - 16）。除了未取代化合物（1,2）已知的脑血管作用外，磺酰胺还显示出显著的外周血管舒张作用。