title: Methanolysis products of disorazole A1.
abstract: Two new disorazole analogues were synthesized by acid-promoted methanolysis of disorazole A1 (1). Structural elucidation of both products (2 and 3), through 1D and 2D NMR experiments, verified that each resulted from epoxide cleavage. With antiproliferative activities in susceptible cell lines comparable to that of disorazole A1, these methanolysis products indicate that the C-9-C-10 epoxide is not an essential structural component for biological activity.
authors.affiliation: Kosan Biosciences, Inc., 3832 Bay Center Place, Hayward, California 94545, USA. hearn@kosan.com
authors.forename: Brian R
authors.initials: BR
authors.lastname: Hearn
authors.forename: Robert L
authors.initials: RL
authors.lastname: Arslanian
authors.forename: Hong
authors.initials: H
authors.lastname: Fu
authors.forename: Fenghua
authors.initials: F
authors.lastname: Liu
authors.forename: Hugo
authors.initials: H
authors.lastname: Gramajo
authors.forename: David C
authors.initials: DC
authors.lastname: Myles
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D004852:Epoxy Compounds / Q000737:chemistry; D018942:Macrolides; D000432:Methanol / Q000737:chemistry*; D015394:Molecular Structure; D009231:Myxococcales / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D004852:Epoxy Compounds; D018942:Macrolides; D010080:Oxazoles; C508682:disorazole A1; D000432:Methanol