Cyclic platelet-activating factor analogues derived from 2-deoxy-d-erythro-pentose

✍ Scribed by Michael L. Phillips; Rosanne Bonjouklian

• Book ID: 102641451
• Publisher: Elsevier Science
• Year: 1986
• Tongue: English
• Weight: 404 KB
• Volume: 146
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(86)85026-1

✦ Synopsis

A method for the synthesis of chiral cyclic analogues of platelet-activating factor (PAF) is reported. Treatment of suitably substituted derivatives of 2-deoxy-D-erythro-pentose with phosphorus oxychloride, followed by choline p-toluenesulfonate generates cyclic phospholipids in good yield. Further chemical modification produces other compounds including optically active gamma-butyrolactones such as 2-deoxy-5-O-hexadecyl-3-O-phosphocholyl-D-erythro-pentono-1, 4-lactone and 2-deoxy-3-O-hexadecyl-5-O-phosphocholyl-D-erythro-pentono-1, 4-lactone. All phospholipids were poor antagonists of PAF-induced aggregation of human platelets, and two analogs were poor agonists. The chemistry presented should be useful for the syntheses of other conformationally restricted analogues of PAF.