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Issue 64, 2015

First noscapine glycoconjugates inspired by click chemistry

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Abstract

A number of novel 7-O-noscapine glycoconjugates have been synthesized starting from noscapine, an alkaloid found in the opium plant, via two successive steps. The first step is a selective 7-O-demethylation of noscapine and the next is a subsequent propargylation which affords 7-O-propargyl noscapine (3) in good yield. The structure was confirmed by extensive spectroscopic data including single crystal X-ray data. The 1,3-dipolar cycloaddition of the developed noscapine derivative 3 with glycosyl azides 6a–m was investigated to give the triazole-linked second-generation noscapine analogs in their glycoconjugate forms (8a–m) to augment the therapeutic efficacy of noscapine.

Graphical abstract: First noscapine glycoconjugates inspired by click chemistry

Supplementary files

Article information


Submitted
22 Apr 2015
Accepted
01 Jun 2015
First published
02 Jun 2015

This article is Open Access

RSC Adv., 2015,5, 51779-51789
Article type
Communication
Author version available

First noscapine glycoconjugates inspired by click chemistry

K. B. Mishra, R. C. Mishra and V. K. Tiwari, RSC Adv., 2015, 5, 51779 DOI: 10.1039/C5RA07321A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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