First noscapine glycoconjugates inspired by click chemistryElectronic supplementary information (ESI) available: Copies of 1H and 13C NMR spectra of all the new compounds and single crystal X-ray data of 3 have been provided. CCDC 1022189. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5ra07321a

• Main Authors: Mishra, Kunj B, Mishra, Ram C, Tiwari, Vinod K
• Format: Journal Article
• Language: English
• Published: 10.06.2015
• ISSN: 2046-2069
• DOI: 10.1039/c5ra07321a

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. The first click chemistry-inspired noscapine glycoconjugates have been developed in good to excellent yields to increase the therapeutic efficacy of noscapine.