The effect of vindoline C-16 substituents on the biomimetic coupling reaction: Synthesis and cytotoxicity evaluation of the corresponding vinorelbine analogues

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• 作者：Weibin Song^a ; ^b ; Lingjun Hu^c ; Yuhui Meng^a ; Lei Ma^b ; Dean Guo^a ; Xuan Liu^a ; ^{xuanliu@mail.shcnc.ac.cn} ; Lihong Hu^a ; ^b ; ^{simmhulh@mail.shcnc.ac.cn}
• 关键词：DABOVROARUPCDQ-QHSXUUMZSA-N ; JDKSWEVAHGGRIB-SHUFHOLNSA-N ; SEUKTCWUQWSDNR-IRCHXDIHSA-N ; PQUWILNUIGECAN-YBMFQFDFSA-N ; TULMLJXKGUAQIV-CJAVQSORSA-N ; KEGHZFJZWBANJM-VGCNAVONSA-N ; ZHPYQRIJHMVCOW-YBMFQFDFSA-N ; JQDXSVRJYRVVGK-KIVAGNRCSA-N ; KCDPGXKIPSTSTE-CJAVQSOR
• 刊名：Bioorganic and Medicinal Chemistry Letters
• 出版年：2012
• 出版时间：15 May, 2012
• 年：2012
• 卷：22
• 期：10
• 页码：3485-3487
• 全文大小：344 K

文摘

A new series of vinorelbine analogues are designed and synthesized to explore the vindoline C-16 substituent effects on the biomimetic coupling with catharanthine, and the structure-activity relationships of these vinorelbine analogues as cytotoxic agents are also studied. The results show that introduction of severe steric hindrance and/or electron-withdrawing group at C-16 site are not propitious to improving the yields of the coupling reaction, and the SAR information collected so far suggests that small alkyl groups substituted at C-16 of vindoline are conductive to maintaining the cytotoxicity.