3-(2-(3-Pyridinyl)thiazolidin-4-oyl)indoles, a Novel Series of Platelet Activating Factor Antagonists
Journal of Medicinal Chemistry1994Vol. 37(13), pp. 2011–2032
Citations Over TimeTop 10% of 1994 papers
George S. Sheppard, Daisy Pireh, George M. Carrera, Mark G. Bures, H. Robin Heyman, Douglas H. Steinman, Steven K. Davidsen, James G. Phillips, Denise E. Guinn, Paul D. May, Richard Conway, David A. Rhein, William C. Calhoun, Daniel H. Albert, Terrance J. Magoc, George W. Carter, James B. Summers
Abstract
(2RS,4R)-3-(2-(3-Pyridinyl)thiazolidin-4-oyl)indoles represent a new class of potent, orally active antagonists of platelet activating factor (PAF). The compounds were prepared by acylation of the magnesium or zinc salts of substituted indoles with (2RS,4R)-2-(3-pyridinyl)-3-(tert-butoxycarbonyl)thiazolidin-4-oyl chloride. The 3-acylindole moiety functions as a hydrolytically stabilized and conformationally restricted anilide replacement, which imparts a considerable boost in potency to the series. Structure-activity relationships observed for substitution on the indole ring system are discussed. Members of the series compare favorably with other reported PAF antagonists.
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