2-氰基-3,12-双氧代齐墩果烷-1,9(11)-双烯-28-羧酸的合成工艺改进  

Improved synthesis of 2-cyano-3,12-dioxooleana-1,9( 11)-dien-28-oic acid

作　　者：肖余 罗群峰 李其星[1] 裴江鸿 陈莉[1] 

机构地区：[1]中国药科大学天然药物化学教研室,江苏南京210009

出　　处：《中国药物化学杂志》2016年第2期131-135,共5页Chinese Journal of Medicinal Chemistry

摘　　要：目的改进2-氰基-3,12-双氧代齐墩果烷-1,9(11)-双烯-28-羧酸(CDDO)的合成工艺。方法以齐墩果酸为起始原料,经苄基化、氧化、催化氢化等7步连续反应合成CDDO。结果与结论 CDDO的结构经质谱、核磁共振氢谱以及红外光谱分析确证,改进后的方法与原工艺相比,工艺简单、环境友好、条件温和、成本低,总收率由文献方法的28.5%提高为39%。2-Cyano-3,12-dioxooleana-1,9 （ 11 ） -dien-28-oic acid （ CDDO ） is one of the most effective semi- synthetic triterpenoids, and its derivatives are known as the most potent anti-inflammatory and anti-carcinogenic oleananes, but the synthetic method is very complicated. In this paper, a synthetic route to CDDO was designed on the basis of references and the synthetic process was also investigated and optimized. CDDO was synthesized from oleanolic acid via 7-step successive reactions including benzylation, oxidation, catalytic hydrogenation,etc. The structure of CDDO was verified by IR, MS and 1H-NMR. The improved method is moderate and the operation is convenient. Meanwhile the synthetic route is environment friendly and costs little. What＇s more the total yield is increased to 39% from 28.5% of the reference.

关 键 词：工艺改进 合成 2-氰基-3 12-双氧代齐墩果烷-1 9(11)-双烯-28-羧酸(CDDO) 抗肿瘤 

分 类 号：R914.5[医药卫生—药物化学]