Use of acetylacetone to prepare a prodrug of cycloserine.
Several derivatives of cycloserine (1) were prepared and it was found that (R)-4-[(1-methyl-3-oxo-1-butenyl)-amino]-3-isoxazolidinone (11), the condensation product of acetylacetone and cycloserine (1), was an efficacious prodrug of increased stability under aqueous conditions.
D000818:Animals; D003523:Cycloserine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology / Q000652:urine; D004355:Drug Stability; D004926:Escherichia coli / Q000187:drug effects; D005260:Female; D007659:Ketones; D051379:Mice; D010422:Pentanones; D013211:Staphylococcus aureus / Q000187:drug effects
D007659:Ketones; D010422:Pentanones; C008790:acetylacetone; D003523:Cycloserine