Cholesterol surrogates incorporating a benzophenone as part of the sterol tetracycle.
Cholesterol surrogates incorporating a benzophenone as part of the sterol tetracycle.
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DOI：
10.1021/jo060480y
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发表时间：
2006-07
期刊：
影响因子：
--
通讯作者：
Yonghong Gan;T. A. Spencer
中科院分区：
文献类型：
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作者：
Yonghong Gan;T. A. Spencer
胆固醇 (1) 的光活化类似物 4-6 的交联位点位于环 D 甾醇区域，从溴四氢酮 14 开始，通过对映选择性 Robinson 成环形成烯酮 13，并通过 Suzuki 羰基化偶联至适当的苯基硼酸。在 apo A-I 诱导的细胞胆固醇流出测定中，4-6 中的每一个都被证明可以成功替代 1，这表明这些类似物在所有主要细胞池中与 1 达到平衡。
Photoactivatable analogues 4-6 of cholesterol (1), having their cross-linking site in the ring D sterol region, have been synthesized starting from bromotetralone 14 via enantioselective Robinson annulation to enone 13 and Suzuki carbonylative coupling to the appropriate phenylboronic acid. Each of 4-6 was shown to substitute successfully for 1 in an assay of apo A-I-induced cellular cholesterol efflux, indicating that these analogues equilibrated with 1 in all major cellular pools.