3-[(Z)-十五碳-8-烯基]儿茶酚的全合成及其抗肿瘤血管生成活性研究有机化学.pdfVIP

DOI: 10.6023/cjoc201301006 研究论文 有机化学 Chinese Journal of Organic Chemistry ARTICLE 3-[(Z)-十五碳-8-烯基]儿茶酚的全合成及其抗肿瘤血管生成活性研究 杨 梅a,c 何江波a 程永现*,a 蒋 晟*,b (a 中国科学院昆明植物研究所 植物化学与西部植物资源持续利用国家重点实验室 昆明 650204) (b 中国科学院广州生物医药与健康研究院 广州 510530) (c 中国科学院大学 北京 100039) 摘要 以 2,3-二甲氧基苯甲醛为原料, 经过 Barbier 偶联反应, 将邻二酚羟基的保护基从甲基保护转换成缩丙酮保护, 再经Wittig 反应等方法合成了3-[(Z)-十五碳-8-烯基]儿茶酚(GQ-5). 所合成化合物的结构均经 1H NMR, 13C NMR 及 MS (HRMS)进行了鉴定. 采用人脐静脉内皮细胞株对 GQ-5 的抗肿瘤血管生成活性进行了评价. 关键词 漆酚; 干漆; Wittig 反应; 抗肿瘤血管生成 Synthesis of 3-[(Z)-Pentadec-8-enyl]catechol and Its Anti-angiogenesis Activity Yang, Meia,c He, Jiangboa Cheng, Yongxian*,a Jiang, Sheng*,b a ( State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204) (b Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou 510530) (c University of Chinese Academy of Sciences, Beijing 100039) Abstract 3-[(Z)-Pentadec-8-enyl]catechol (GQ-5) was produced from 2,3-dimethoxybenzaldehyde through Barbier coupling reaction, the conversion of protecting group from methyl ether to acetonylidene, Wittig reaction and so on. These compounds have been confirmed by 1H NMR, 13C NMR and MS (or HRMS) techniques. Meanwhile, anti-angiogenesis activity of com- pound GQ-5 was evaluated by using HUVEC cells. Keywords urushiol; resina toxicodendri; Wittig reaction; an