title: A new synthesis of cytoxazone and its diastereomers provides key initial SAR information.
abstract: A short, enantioselective, and diastereoselective synthesis of cytoxazone, a Th2-selective immunomodulator from Streptomyces, is described. The route was readily adapted to the synthesis of the three other stereoisomers of natural cytoxazone. Evaluation of these compounds revealed that the stereochemical configuration of the oxazolidinone ring did not influence their biological activity.
authors.affiliation: Bristol-Myers Squibb Company, Pharmaceutical Research Institute, Princeton, NJ 08543-4000, USA. percy.carter@bms.com
authors.forename: Percy H
authors.initials: PH
authors.lastname: Carter
authors.forename: Jacob R
authors.initials: JR
authors.lastname: LaPorte
authors.forename: Peggy A
authors.initials: PA
authors.lastname: Scherle
authors.forename: Carl P
authors.initials: CP
authors.lastname: Decicco
mesh_terms: D000215:Acylation; D000276:Adjuvants, Immunologic / Q000138:chemical synthesis* / Q000494:pharmacology*; D000818:Animals; D004305:Dose-Response Relationship, Drug; D066298:In Vitro Techniques; D016753:Interleukin-10 / Q000037:antagonists & inhibitors / Q000378:metabolism; D007376:Interleukin-2 / Q000037:antagonists & inhibitors / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D010080:Oxazoles / Q000138:chemical synthesis* / Q000494:pharmacology*; D011043:Pokeweed Mitogens / Q000037:antagonists & inhibitors / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D018418:Th2 Cells / Q000187:drug effects / Q000378:metabolism
chemical_list: D000276:Adjuvants, Immunologic; D007376:Interleukin-2; D010080:Oxazoles; D011043:Pokeweed Mitogens; D016753:Interleukin-10; C117832:cytoxazone