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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 被引量：1

Improved synthesis of 2-cyano-3,12-dioxooleana-1,9( 11)-dien-28-oic acid
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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.
作者 肖余 罗群峰 李其星 裴江鸿 陈莉
机构地区 中国药科大学天然药物化学教研室
出处 《中国药物化学杂志》 CAS CSCD 2016年第2期131-135,共5页 Chinese Journal of Medicinal Chemistry
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 process improvement synthesis CDDO antitumor
分类号 R914.5 [医药卫生—药物化学]
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参考文献9

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二级参考文献32

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中国药物化学杂志
2016年 第2期

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