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Synthesis of chiral 1,4-disubstituted-1,2,3-triazole derivatives from amino acids.

ABSTRACT: 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.

SUBMITTER: Klein M

PROVIDER: S-EPMC6255254 | biostudies-literature | 2009

REPOSITORIES: biostudies-literature

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Synthesis of chiral 1,4-disubstituted-1,2,3-triazole derivatives from amino acids.

Klein Michael M Krainz Karin K Redwan Itedale Namro IN Dinér Peter P Grøtli Morten M

Molecules (Basel, Switzerland) 20091209 12

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 n ...[more]

PMID: 20032880

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