The Condensation Reaction of Carbohydrates with Phisioligical Activity Heterocyclic Compounds

Author: Ramaz Gakhokidze
Co-authors: N. Sidamonidze, R.Vardiashvili, M.Nutsubidze, M.Tatarishvili
Keywords: Heterocyclic, Nitrozocompounds
Annotation:

Modification of carbohydrates by various types of organic compounds has recently played a significant role in the synthesis of new of biological and pharmacologically active compounds. Little has been published about carbohydrates containing heterocyclic compounds and nitrozo group. The application of glycosides for the modification of biologically active organic compounds of sulfo and nitrogen may, on the one hand, change their biological and physiological action, and on the other, may reduce their toxicity. The goal of present investigation consist in in synthesis of O- and N-glycosides containing in a molecule thiazolyl- and nitrosogroup. The condensation reaction of 1-chloro-2,3,4,6-tetra-O-acetyl- -Dgluco( galacto)pyranose with 4,4,8,8-tetramethyl-2,3,6,7-dibenzo-9-oxabicyclo-(3,3,1)- nonan-1-N-(4-methyltiazolylethylamino)-5-ol in the presence of the silver carbonate catalyst has been studied аt the first time. As the experimental result have been obtained corresponding dibenzooxabicyclothiazolylaminocontaining O-glycosides. The reaction condensation of N-p-carboxyphenyl--D-gluco(galacto)pyranozilamine with N,N'-Dicyclohexylcarbodiimide in the prezenc of tetrahydrofuran and triethylamine was studied for the ferst time. By interaction of obtained N-acylureas with sodium nitrite corresponding nitrosoderivatives have been received The structures of obtained compounds were established by physical-chemical methods of analysis. In order to justify theoretical direction of the reactions a quantum-chemical calculations have been perfomed.