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具有双环[2.2.1]庚烷、双环[3.1.1]庚烷和双环[2.2.2]辛烷环系的前列腺素的合成。15-羟基差向异构体对人血小板的活性。

Synthesis of prostanoids with bicyclo[2.2.1]heptane, bicyclo[3.1.1]heptane, and bicyclo[2.2.2]octane ring systems. Activities of 15-hydroxy epimers on human platelets.

作者信息

Wilson N H, Peesapati V, Jones R L, Hamilton K

出版信息

J Med Chem. 1982 May;25(5):495-500. doi: 10.1021/jm00347a004.

DOI:10.1021/jm00347a004
PMID:7086834
Abstract

A number of prostanoids with bicyclo[2.2.1]heptane, bicyclo[3.1.1]heptane, and bicyclo[2.2.2]octane ring systems have been prepared by routes which allow the introduction of the omega chain after the alpha chain. The introduction of a 16-p-halophenoxy substituent confers platelet aggregation activity on both 15 alpha- and 15 beta-hydroxy epimers. In the case of the pinane thromboxane ring system, the natural omega-chain compound is an inhibitor of aggregation, whereas the 16-p-fluorophenoxy analogue is a potent aggregation agent.

摘要

通过一些能在引入α链后再引入ω链的方法,已制备出了多种具有双环[2.2.1]庚烷、双环[3.1.1]庚烷和双环[2.2.2]辛烷环系的前列腺素类化合物。引入一个16 - 对 - 卤代苯氧基取代基会使15α - 和15β - 羟基差向异构体都具有血小板聚集活性。就蒎烷血栓素环系而言,天然的ω链化合物是聚集抑制剂,而16 - 对 - 氟苯氧基类似物则是强效聚集剂。

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Biochem J. 1984 May 1;219(3):833-42. doi: 10.1042/bj2190833.
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Increased platelet thromboxane receptor sensitivity in diabetic patients with proliferative retinopathy.
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Diabetologia. 1986 Aug;29(8):471-4. doi: 10.1007/BF00453495.
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Biochem J. 1986 Feb 1;233(3):707-18. doi: 10.1042/bj2330707.
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