Design, Synthesis and Pharmacological Evaluation of Noscapine Glycoconjugates

Abstract

The present work is directed to design a series of molecules which are hybrids of two non-toxic biocompatible chemical architectures, noscapine and carbohydrates. Fourteen, 7-O-noscapine analogues have been synthesized out of which one of the analogue is 7-O-propargylated derivative and others are in its glycoconjugate form with triazole bridging achieved via Click reaction, where dinuclear copper(I) thiodiacetate complex [(PPh 3 ) 2 Cu(μ-tda)Cu(PPh 3 ) 2 ].6H 2 O has been emerged as an excellent catalyst for the noscapine-glyco Click-coupling. All the developed noscapine glycoconjugates have been investigated for anticancer activity using HeLa cell line and anti-leishmanial activity against Leishmania donovani. Result indicates that five of the developed noscapine glycoconjugates (5 a, 5 b, 5 c, 5 e and 5 l) showed significant anti-proliferative activity. On the other hand, four of them (5 b, 5 c, 5 e, and 5 l) showed significant anti-leishmanial activity. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim