Abstract
A series of 24 novel triazole-linked flavonol glycoconjugates 1~24 were synthesized using flavonols (Kaempferol, Rhamnocitrin or 7,5,4’-trimethoxy flavonol) and carbohydrates (glucose, galactose, lactose or maltose) as starting materials by a “Click chemistry” approach. Intermolecular Cu (I) catalyzed 1,3-dipolar cycloaddition of propargyl ethers of flavonols and glycosyl azides is the key step. Their cytotoxic potential against four human cancer cell lines (HL- 60, SMMC-7721, A-549 and MCF-7) was evaluated by standard MTT method. The results showed that 1, 3, 5, 6, 12 and 13 exhibit moderate to potent cytotoxicity against these cancer cell lines comparable with the positive control, cis- Platinum (DDP).
Keywords: Cytotoxic activity, Click chemistry, Flavonol, Glycoconjugates.
Letters in Organic Chemistry
Title:A Facile “Click Chemistry” Approach to Novel Flavonol Glycoconjugates and Their Cytotoxic Activity
Volume: 10 Issue: 9
Author(s): Wu Zheng, Nguyen Van-son, Liu Zhang-kun and Wang Qiu-an
Affiliation:
Keywords: Cytotoxic activity, Click chemistry, Flavonol, Glycoconjugates.
Abstract: A series of 24 novel triazole-linked flavonol glycoconjugates 1~24 were synthesized using flavonols (Kaempferol, Rhamnocitrin or 7,5,4’-trimethoxy flavonol) and carbohydrates (glucose, galactose, lactose or maltose) as starting materials by a “Click chemistry” approach. Intermolecular Cu (I) catalyzed 1,3-dipolar cycloaddition of propargyl ethers of flavonols and glycosyl azides is the key step. Their cytotoxic potential against four human cancer cell lines (HL- 60, SMMC-7721, A-549 and MCF-7) was evaluated by standard MTT method. The results showed that 1, 3, 5, 6, 12 and 13 exhibit moderate to potent cytotoxicity against these cancer cell lines comparable with the positive control, cis- Platinum (DDP).
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Cite this article as:
Zheng Wu, Van-son Nguyen, Zhang-kun Liu and Qiu-an Wang, A Facile “Click Chemistry” Approach to Novel Flavonol Glycoconjugates and Their Cytotoxic Activity, Letters in Organic Chemistry 2013; 10 (9) . https://dx.doi.org/10.2174/15701786113109990039
DOI https://dx.doi.org/10.2174/15701786113109990039 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
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