New cyanomorpholinyl byproduct of doxorubicin reductive alkylation

EM Acton, GL Tong, DL Taylor, JA Filppi…

Index: Acton, Edward M.; Tong, George L.; Taylor, Dorris L.; Filppi, Joyce A.; Wolgemuth, Richard L. Journal of Medicinal Chemistry, 1986 , vol. 29, # 7 p. 1225 - 1230

Full Text: HTML

Citation Number: 12

Abstract

Previously we reported that reductive alkylation of doxorubicin with 2, 2'-oxybis [acetaldehyde] and NaBH, CN to form the 4”-morpholinyl derivative also gave the intensely potent 3”-cyano-4”-morpholiiylas a byproduct, by addition of CN-to an iminium intermediate in place of hydride. We now find that sugar 4'-OH is a third nucleophile that can add to the iminium intermediate in this reaction. Bridging of the 4'-OH to the morpholine ring at C. 5” ...