The synthesis of an aminohexyl-containing analog of the chromanol leukotriene B-4 receptor antagonist CP-195543: A scaffold for the preparation of derivatized analogs
Heterocycles(2000)
摘要
In order to allow the preparation of labeled derivatives of the leukotriene B-4 (LTB4) antagonist CP-195543 for the study and/or "visualization" of LTB4 receptors in in vitro and in vivo settings, we have synthesized an aminohexyl-containing analog (2) as a scaffold from which the requisite compounds can be prepared. The key reactions in the preparation of 2 include the DAST-mediated introduction of a difluoromethylene group in the presence of an azide and a Suzuki coupling between this highly functionalized benzoate and a chromanol-derived boronic acid. 2-(3S,4R)-(3-Benzyl-4-hydroxychroman-7-yl)-4(1,1 -difluoro-7-methanesulfonamidoheptyl)benz acid (12), prepared from 2 by methanesulfonylation and saponification, is a potent LTB4 receptor antagonist but displays a high degree of non-specific binding.
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关键词
radiolabeling,Suzuki coupling reaction,DAST
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