Antineoplastic Agents. 579. Synthesis and Cancer Cell Growth Evaluation of E-Stilstatin 3: A Resveratrol Structural Modification

作者:Pettit George R*; Melody Noeleen; Thornhill Andrew; Knight John C; Groy Thomas L; Herald Cherry L
来源:Journal of Natural Products, 2009, 72(9): 1637-1642.
DOI:10.1021/np9002146

摘要

As an extension of our earlier structure/activity investigation of resveratrol (1a) cancer cell growth inhibitory activity compared to the structurally related stilbene combretastatin series (e.g., 2a), an efficient synthesis of E-stilstatin 3 (3a) and its phosphate prodrug 3b was completed. The trans-stilbene 3a was obtained using a convergent synthesis employing a Wittig reaction with phosphonium bromide 9 as the key reaction step. Deprotection of the Z-silyl ether 13 gave E-stilstatin 3 (3a) as the exclusive product. The structure and stereochemistry of 3a was confirmed by X-ray crystal structure determination.

  • 出版日期2009-9