„Synthesis and prediction biological activity of some derivatives of N-(4-carboxyphenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine“

Author: Mariam Archvadze
Keywords: The condensation reactions ofof N-β-(p-carboxyphenyl)-D-glucopyranosylamine
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A n n o t a t i o n Mariam Archvadze „Synthesis and prediction biological activity of some derivatives of N-(4-carboxyphenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine“ Department of Chemistry, Iv. Javakhishvili Tbilisi State University Ilia Chavchavadze Ave. 3 The N-β-glycosidic bond is widely represented in a large number of natural compounds, primarily in nucleic acids and glycoproteins, some coenzymes, as well as synthetic analogues of nucleotides, the antimetabolites, which are used in the treatment of tumor diseases and viral infections. The development of efficient synthetic methodologies for various N-glycosides and their derivatives will be useful in designing and preparing synthetic natural product analogues. The goal of our work was to synthesize of glucoconjugates of N-(4-carboxyphenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine (III) and prediction of their biological activity. N-(4-carboxyphenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine has been synthesized from D-glucose and 4-aminobenzoic acid by refluxing in 95% methanol in the presence of a NH4Cl catalyst andby the further acetilation of synthesizedN-(4-carboxyphenyl)-β-D-glucopyranosylamine.By condensation of N-(4-carboxyphenyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine with H-L-Gly ethyl ester hydrochloride end H-L-His methyl ester dihydrochloride in the presence of dicyclohexylcarbodiimide and triethylamine at 0C temperature, the corresponding derivatives heve been obtained for the first time. The structures of obtainedcompounds were established by physical-chemical methods ofanalysis. With the help of computer program PASSO nline basedon the analysis of structure activity- relationships wide range of the prediction data of possible biological activity and toxic/side effectsfor synthesized compounds has been predicted.

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