Synthesis and biological properties of 4-amino- and 4-bromo-4-norpyridoxol. New approaches for the modification of the 4 position of vitamin B6
- 1 August 1976
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 19 (8) , 999-1002
- https://doi.org/10.1021/jm00230a003
Abstract
4-Amino-4-norpyridoxol, a new key intermediate for the modification of the 4 position of vitamin B6, was obtained by an unusual photochemical rearrangement of pyridoxal oxime. It was also synthesized starting from 3,.alpha.5-O-dibenzylpyridoxal, which was converted to 3,.alpha.5-O-dibenzylpyridoxamide. The latter, on Hoffman reaction, gave the desired 3,5-blocked 4-amino derivative. Several derivatives of this analog were prepared, and its existence in the amino tautomeric form were established by NMR spectroscopy. A modified Sandmeyer reaction on 4-amino-4-norpyridoxol gave the 4-bromo analog, which was moderately active as an inhibitor of mouse mammary adenocarcinoma cells grown in cell culture, whereas the 4-amino analog was not active at 10-4 M. Other analogs containing electron withdrawing and electron donating substituents in the 4 position of pyridoxine were also tested.This publication has 1 reference indexed in Scilit:
- Vitamin B6 Analogs. I. 5-Hydroxy-6-methyl-4-trifluoromethyl-3-pyridinemethanol Hydrochloride1Journal of Medicinal Chemistry, 1963