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.
MeSH terms
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Acylation
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Adjuvants, Immunologic / chemical synthesis*
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Adjuvants, Immunologic / pharmacology*
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Animals
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Dose-Response Relationship, Drug
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In Vitro Techniques
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Interleukin-10 / antagonists & inhibitors
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Interleukin-10 / metabolism
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Interleukin-2 / antagonists & inhibitors
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Interleukin-2 / metabolism
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Magnetic Resonance Spectroscopy
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Mice
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Oxazoles / chemical synthesis*
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Oxazoles / pharmacology*
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Pokeweed Mitogens / antagonists & inhibitors
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Pokeweed Mitogens / pharmacology
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Stereoisomerism
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Structure-Activity Relationship
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Th2 Cells / drug effects
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Th2 Cells / metabolism
Substances
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Adjuvants, Immunologic
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Interleukin-2
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Oxazoles
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Pokeweed Mitogens
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Interleukin-10
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cytoxazone