ISSN:
0947-3440
Keywords:
Vitamin A derivatives
;
Retinoic acid derivatives
;
Tumor inhibitors
;
Koenigs-Knorr reaction
;
Glucuronides
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The toxic and teratogenic effects caused by the highly biologically active (all-E)-retinoic acid and its derivatives prompted us to synthesize a number of retinoids. We developed synthetic approaches to (all-E)-retinyl β-D-glucuronide 3, methyl (retinoyl β-D-glucopyranoside)uronate 5, (all-E)-retinoic acid β-D-glucopyranosyl ester 8 and (all-E)-retinoyl β-D-glucuronide 6 in high purity and yield. Compound 3 was synthesized under Koenigs-Knorr conditions from (all-E)-retinol and an α-halogenose. Compounds 5 and 8 were prepared by esterification of a silver salt of (all-E)-retinoic acid with an α-glycosyl halide in pyridine. (all-E)-Retinoyl β-D-glucuronide 6 was prepared by reaction of (all-E)-retinoyl fluoride with underivatized β-D-glucuronic acid. Compounds 5, 6 and 8 show biological effects similiar to those of retinoic acid.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1995199504106
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