Next Article in Journal
The Chemical Composition and Biological Properties of Coconut (Cocos nucifera L.) Water
Previous Article in Journal
Calpain Inhibition Reduces Axolemmal Leakage in Traumatic Axonal Injury
Article Menu

Article Versions

Export Article

Open AccessArticle
Molecules 2009, 14(12), 5124-5143; doi:10.3390/molecules14125124

Synthesis of Chiral 1,4-Disubstituted-1,2,3-Triazole Derivatives from Amino Acids

Department of Chemistry, Medicinal Chemistry, University of Gothenburg, SE-412 96 Göteborg, Sweden
*
Author to whom correspondence should be addressed.
Received: 13 November 2009 / Revised: 26 November 2009 / Accepted: 7 December 2009 / Published: 9 December 2009
Download PDF [240 KB, uploaded 18 June 2014]

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.
Keywords: [3+2] cycloaddition; azido alcohols; 1,4-disubstituted-1,2,3-triazoles [3+2] cycloaddition; azido alcohols; 1,4-disubstituted-1,2,3-triazoles
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Klein, M.; Krainz, K.; Redwan, I.N.; Dinér, P.; Grøtli, M. Synthesis of Chiral 1,4-Disubstituted-1,2,3-Triazole Derivatives from Amino Acids. Molecules 2009, 14, 5124-5143.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top