Copper(I) mediated facile synthesis of potent tubulin polymerization inhibitor, 9-amino-伪-noscapine from natural 伪-noscapine

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• 作者：Naresh K. Manchukonda^a ; Balasubramanian Sridhar^b ; Pradeep K. Naik^c ; Harish C. Joshi^d ; Srinivas Kantevari^a ; ^{kantevari@gmail.com} ; ^{kantevari@yahoo.com}
• 关键词：Noscapine ; Amino-noscapine ; Copper iodide ; Tubulin polymerization ; Isoquinoline alkaloid
• 刊名：Bioorganic and Medicinal Chemistry Letters
• 出版年：2012
• 期刊代码：10_0960894x
• 类别：ch
• 出版时间：15 April, 2012
• 卷：22
• 期：8
• 页码：2983-2987
• 文件大小：652 K

摘要

Facile synthesis of natural 伪-noscapine analogue, 9-amino-伪-noscapine, a potent inhibitor of tubulin polymerization for cancer therapy, is achieved via copper(I) iodide mediated in situ aromatic azidation and reduction of 9-bromo-伪-noscapine (obtained by bromination of natural 伪-noscapine) with NaN₃ in DMSO at 130 掳C in the presence of l-proline as an amino acid promoter. The protocol developed here avoided isolation of 9-azido-伪-noscapine and did not cleave the sensitive C-C bond between two heterocyclic phthalide and isoquinoline units.