Issue 64, 2015

First noscapine glycoconjugates inspired by click chemistry


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

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Article information

Article type
22 Apr 2015
01 Jun 2015
First published
02 Jun 2015
This article is Open Access
Creative Commons BY license

RSC Adv., 2015,5, 51779-51789

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

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