抗肿瘤药。565. 考布他汀 D-2 磷酸酯和二氢考布他汀 D-2 的合成。
Antineoplastic agents. 565. Synthesis of combretastatin D-2 phosphate and dihydro-combretastatin D-2.
机构信息
Department of Chemistry and Biochemistry, Cancer Research Institute, Arizona State University, PO Box 871604, Tempe, Arizona 85287-1604, USA.
出版信息
J Nat Prod. 2009 May 22;72(5):876-83. doi: 10.1021/np800635h.
Abstract
A modified synthetic route to combretastatin D-2 (5) was devised in order to further evaluate its biological activity, for its conversion to phosphate prodrugs (25-28), and as a route to obtaining dihydro-combretastatin D-2 (42). A parallel first total synthesis of dihydro-combretastatin D-2 was completed, proceeding from a saturated 3-phenylpropionic ester intermediate via the Ullmann biaryl ether reaction (39-41). In contrast to the cancer cell growth inhibitory activity exhibited by combretastatin D-2, relatively minor structural modifications (41, 42) caused elimination of those properties.
摘要
为了进一步评估其生物活性、将其转化为磷酸盐前药（25-28）以及作为获得二氢康普瑞汀 D-2（42）的途径，设计了一种改良的康普瑞汀 D-2（5）的合成路线。通过 Ullmann 联苯醚反应（39-41），从饱和 3-苯基丙酸酯中间体出发，平行地完成了二氢康普瑞汀 D-2 的首次全合成。与康普瑞汀 D-2 表现出的癌细胞生长抑制活性相反，相对较小的结构修饰（41、42）导致这些性质的消除。
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