Conjugates of 1,2,3-triazoles and acyclic pyrimidine nucleoside analogues: syntheses and X-ray crystallographic studies
| Autor: | Silvija Korunda, Svjetlana Krištafor, Mario Cetina, Silvana Raić-Malić |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2013 |
| Předmět: |
chemistry.chemical_classification
Pyrimidine Stereochemistry Organic Chemistry Alkyne Regioselectivity Cycloaddition chemistry.chemical_compound chemistry Penciclovir medicine Side chain Click chemistry Nucleoside medicine.drug acyclic pyrimidine nucleoside azide-alkyne cycloaddition click chemistry 1 4-disubstituted 1 2 3-triazoles X-ray diffraction supramolecular assembling |
| Popis: | The synthesis of novel acyclic pyrimidine nucleoside analogues with 1, 2, 3-triazole ring bound via ethylene spacer or directly to C-5 of pyrimidine ring has been reported. 1, 4- Disubstituted 1, 2, 3-triazoles were synthesized by click chemistry approach using regioselective copper(I)-catalyzed 1, 3-dipolar cycloaddition reaction between terminal alkyne and azido pyrimidines under both conventional (method A) and microwave (method B) conditions. N-Alkylation of triazolyl pyrimidines afforded 5-[2-(1, 2, 3- triazolyl)ethyl]pyrimidine derivatives with penciclovir-, ganciclovir-like and 2, 3- dihydroxypropyl side chain, as well as 5-(1, 2, 3- triazolyl)pyrimidine derivatives with penciclovir- and ganciclovir-like side chain. The stereostructures of 2-hydroxyethyl, 2- tosyloxyethyl, 2-azidoethyl and 4-acetoxymethyl- 1, 2, 3-triazolyl C-5 substituted pyrimidine derivatives were unambiguously confirmed by their X-ray crystal structure analysis. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|