Methanolysis products of disorazole A1.
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.
Hearn
Brian R
BR
Kosan Biosciences, Inc., 3832 Bay Center Place, Hayward, California 94545, USA. hearn@kosan.com
Arslanian
Robert L
RL
Fu
Hong
H
Liu
Fenghua
F
Gramajo
Hugo
H
Myles
David C
DC
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
D000970:Antineoplastic Agents; D004852:Epoxy Compounds; D018942:Macrolides; D010080:Oxazoles; C508682:disorazole A1; D000432:Methanol