title: Synthesis and antifungal selectivity of new derivatives of amphotericin B modified at the C-13 position.
abstract: The syntheses of the first amphotericin B derivatives to be modified solely at the C-13 hemiketal position are described. Selective functionalisation at this position is facilitated by use of the allyl ester as a C-16 carboxylate protecting group on the amphotericin B nucleus. In in vitro tests all compounds showed markedly reduced haemolytic activity against mammalian erythrocytes while two of the novel 13-alkoxy derivatives retained good antifungal activity.
authors: SmithKline Beecham Pharmaceuticals, Great Burgh, Epsom, Surrey, UK.
authors: A W
authors: AW
authors: Taylor
authors: B J
authors: BJ
authors: Costello
authors: P A
authors: PA
authors: Hunter
authors: W S
authors: WS
authors: MacLachlan
authors: C T
authors: CT
authors: Shanks
mesh_terms: D000666:Amphotericin B / Q000031:analogs & derivatives*; D000818:Animals; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004912:Erythrocytes / Q000187:drug effects; D006736:Horses; D008826:Microbial Sensitivity Tests; D013329:Structure-Activity Relationship
chemical_list: D000935:Antifungal Agents; D000666:Amphotericin B