Issue 16, 2016
From the journal:

RSC Advances

Aglycone mimics for tuning of glycosidase inhibition: design, synthesis and biological evaluation of bicyclic pyrrolidotriazole iminosugars†

Inderpreet Arora,a   Sandeep K. Sharmab  and  Arun K. Shaw*a  

* Corresponding authors

a Division of Medicinal and Process Chemistry, CSIR-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, India
E-mail: akshaw55@yahoo.com

b Microbiology Division, CSIR-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, India

Abstract

Various fuco-configured bicyclic pyrrolidotriazole aglycone mimics were synthesised using copper-catalysed coupling of allyl bromides with terminal alkynes and Sonogashira–Hagihara reaction followed by intramolecular azide-alkyne ‘click’ reaction. The mimicry of the aglycone segment tends to bring about switching of activity amongst α-glucosidases and a 10 to 14-fold enhancement in potency for α-fucosidase inhibition.

Graphical abstract: Aglycone mimics for tuning of glycosidase inhibition: design, synthesis and biological evaluation of bicyclic pyrrolidotriazole iminosugars

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Article information

DOI
https://doi.org/10.1039/C5RA26005A
Article type
Paper
Submitted
06 Dec 2015
Accepted
12 Jan 2016
First published
15 Jan 2016

RSC Adv., 2016,6, 13014-13026

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Aglycone mimics for tuning of glycosidase inhibition: design, synthesis and biological evaluation of bicyclic pyrrolidotriazole iminosugars

I. Arora, S. K. Sharma and A. K. Shaw, RSC Adv., 2016, 6, 13014 DOI: 10.1039/C5RA26005A

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