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Synthesis of chiral 1,4-disubstituted-1,2,3-triazole derivatives from amino acids
Department of Chemistry, Medicinal Chemistry, University of Gothenburg.
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2009 (English)In: Molecules, ISSN 1420-3049, Vol. 14, no 12, 5124-5143 p.Article in journal (Refereed) Published
Abstract [en]

A versatile method for the synthesis of chiral 1,4-disubstituted-1,2,3-triazole derivatives starting from easily accessible naturally occurring D-or L-amino acids as chiral synthons is described. The amino acids were converted into azido alcohols, followed by copper catalyzed [3+2] cycloaddition reactions between the azido alcohols and methyl propiolate and subsequent ester aminolysis with primary and secondary amines furnished the target compounds, which were obtained in excellent yields with no racemization. Docking of selected target compounds shows that the chiral 1,4-disubstituted-1,2,3-triazoles derivatives has the potential of mimicking the binding mode of known purine analogues.

Place, publisher, year, edition, pages
2009. Vol. 14, no 12, 5124-5143 p.
Keyword [en]
[3+2] cycloaddition, azido alcohols, 1, 4-disubstituted-1, 2, 3-triazoles
National Category
Chemical Sciences
URN: urn:nbn:se:uu:diva-121900DOI: 10.3390/molecules14125124ISI: 000273043200021PubMedID: 20032880OAI: oai:DiVA.org:uu-121900DiVA: diva2:306906
Available from: 2010-03-31 Created: 2010-03-31 Last updated: 2011-04-28Bibliographically approved

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Dinér, Peter
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