Document Report Card

ID: ALA3272110

Journal: J Med Chem

Title: Synthesis and biological properties of 4-amino- and 4-bromo-4-norpyridoxol. New approaches for the modification of the 4 position of vitamin B6.

Authors: Korytnyk W, Ghosh AC, Potti PG, Srivastava SC.

Abstract: 4-Amino-4-norpyridoxol, a new key intermediate for the modification of the 4 position of vitamin B6, has been obtained by an unusual photochemical rearrangement of pyridoxal oxime. It has also been synthesized starting from 3,-alpha5-O-dibenzylpyridoxal, which was converted to 3,alpha5-O-dibenzylpyridoxamide. The latter, on Hoffman reaction, gave the desired 3,5-blocked 4-amino derivative. Several derivatives of this analogue have been prepared, and its existence in the amino tautomeric form has been established by NMR spectroscopy. A modified Sandmeyer reaction on 4-amino-4-norpyridoxol gave the 4-bromo analogue, which was found to be moderately active as an inhibitor of mouse mammary adenocarcinoma cells grown in cell culture, whereas the 4-amino analogue was not active at 10(-4)M. Other analogues containing electron-withdrawing and electron-donating substituents in the 4 position of pyridoxine were also tested.

CiteXplore: 966255

DOI: 10.1021/jm00230a003