Efficient synthesis of ethisterone glycoconjugate via bis-triazole linkage.

Carbohydr Res

Department of Chemistry, Centre of Advanced Study, Faculty of Science, Banaras Hindu University, Varanasi 5, India. Electronic address:

Published: November 2014

AI Article Synopsis

  • The research focused on creating sugar-based triazolyl azido-alcohols using a one-pot click reaction of glycosyl alkynes and epichlorohydrin in water.
  • These newly developed compounds were then used to synthesize bis-triazolyl ethisterone glycoconjugates through a CuAAC reaction.
  • The resulting glycoconjugates have potential applications in studying androgen receptor pharmacology and chemical biology.

Article Abstract

Synthesis of sugar based triazolyl azido-alcohols was accomplished via one pot click reaction of glycosyl alkynes with epichlorohydrin in aqueous medium. All the developed triazolyl azido-alcohols were further utilized for the synthesis of bis-triazolyl ethisterone glycoconjugates using CuAAC reaction. The developed triazole-linked ethisterone glycoconjugates would be crucial in androgen receptor pharmacology and chemical biology.

Download full-text PDF

Source
http://dx.doi.org/10.1016/j.carres.2014.09.001DOI Listing

Publication Analysis

Top Keywords

triazolyl azido-alcohols
8
ethisterone glycoconjugates
8
efficient synthesis
4
synthesis ethisterone
4
ethisterone glycoconjugate
4
glycoconjugate bis-triazole
4
bis-triazole linkage
4
linkage synthesis
4
synthesis sugar
4
sugar based
4

Similar Publications

The design, synthesis and biological study of several novel 1,2,3-triazolyl [Formula: see text]-hydroxy alkyl/carbazole hybrid molecules as a new type of antifungal agent has been described. In this synthesis, the N-alkylation reaction of carbazol-9-ide potassium salt with 3-bromoprop-1-yne afforded 9-(prop-2-ynyl)-9H-carbazole. The 'Click' Huisgen cycloaddition reaction of 9-(prop-2-ynyl)-9H-carbazole with diverse [Formula: see text]-azido alcohols in the presence of copper-doped silica cuprous sulphate led to target molecules in excellent yields.

View Article and Find Full Text PDF

A simple and efficient synthesis of novel, D-ring substituted estrone derivatives containing a 16α-triazolyl moiety is described. Two epimeric azido alcohols (16α-azido-17α-hydroxy and 16α-azido-17β-hydroxy) of estra-1,3,5(10)-triene-3-methyl ether were prepared, followed by copper(I)-catalyzed azide-alkyne cycloaddition with various terminal alkynes. The steroidal triazoles were obtained in high yields and their activities against three human cancer cell lines (HeLa, MCF7 and A431) were screened.

View Article and Find Full Text PDF

Efficient synthesis of ethisterone glycoconjugate via bis-triazole linkage.

Carbohydr Res

November 2014

Department of Chemistry, Centre of Advanced Study, Faculty of Science, Banaras Hindu University, Varanasi 5, India. Electronic address:

Article Synopsis
  • The research focused on creating sugar-based triazolyl azido-alcohols using a one-pot click reaction of glycosyl alkynes and epichlorohydrin in water.
  • These newly developed compounds were then used to synthesize bis-triazolyl ethisterone glycoconjugates through a CuAAC reaction.
  • The resulting glycoconjugates have potential applications in studying androgen receptor pharmacology and chemical biology.
View Article and Find Full Text PDF

Click chemistry inspired synthesis of morpholine-fused triazoles.

J Org Chem

June 2014

Department of Chemistry, Centre of Advanced Study, Faculty of Science, Banaras Hindu University, Varanasi-221005, India.

Article Synopsis
  • The synthesis of triazolyl azido alcohols involves a one-pot methodology using terminal alkyne and epichlorohydrin, followed by a click reaction with alkyne and azidation of chlorohydroxy triazoles.
  • These triazolyl azido alcohols are then used to create various morpholine-fused triazoles that have potential chemotherapeutic benefits.
  • The structures of the newly developed compounds were characterized using techniques like IR, NMR, MS, and elemental analysis, with four specifically analyzed through single-crystal X-ray analysis.
View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!