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Paper | Regular issue | Vol 53, No. 8, 2000, pp.1713-1724
Published online, 1st January, 1970
DOI: 10.3987/COM-00-8919
The Synthesis of an Aminohexyl-containing Analog of the Chromanol Leukotriene B4 Receptor Antagonist CP-195543: A Scaffold for the Preparation of Derivatized Analogs

Brian P. Jones, Klaas Schildknegt, Kathyrn F. Wright, Henry J. Showell, James P. Dittami, Keith E. McCarthy, and Lawrence A. Reiter*

*Pfizer Inc., Central Research Division, Eastern Point Road, Groton, Connecticut 06340, U.S.A.


In order to allow the preparation of labeled derivatives of the leukotriene B4 (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)benzoic acid (12), prepared from 2 by methanesulfonylation and saponification, is a potent LTB4 receptor antagonist but displays a high degree of non-specific binding.