Design and synthesis of new chacones substituted with azide/triazole groups and analysis of their cytotoxicity towards HeLa cells

Graziele D da Silva; Marina G da Silva; Estrela M P V E Souza; Andersson Barison; Sarah C Simões; Fernando P Varotti; Leandro A Barbosa; Gustavo H R Viana; José A F P Villar

doi:10.3390/molecules170910331

Design and synthesis of new chacones substituted with azide/triazole groups and analysis of their cytotoxicity towards HeLa cells

Molecules. 2012 Aug 29;17(9):10331-43. doi: 10.3390/molecules170910331.

Authors

Graziele D da Silva¹, Marina G da Silva, Estrela M P V E Souza, Andersson Barison, Sarah C Simões, Fernando P Varotti, Leandro A Barbosa, Gustavo H R Viana, José A F P Villar

Affiliation

¹ Laboratório de Síntese Orgânica, Universidade Federal de São João Del Rei, Campus Centro Oeste Dona Lindu, 35.501-296 Divinópolis/MG, Brazil.

Abstract

A series of new chalcones substituted with azide/triazole groups were designed and synthesized, and their cytotoxic activity was evaluated in vitro against the HeLa cell line. O-Alkylation, Claisen-Schmidt condensation and Cu(I)-catalyzed cycloaddition of azides with terminal alkynes were applied in key steps. Fifteen compounds were tested against HeLa cells. Compound 8c was the most active molecule, with an IC₅₀ value of 13.03 μM, similar to the value of cisplatin (7.37 μM).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkylation / drug effects
Azides / chemistry*
Catalysis
Cell Death / drug effects*
Cell Line, Tumor
Cell Survival / drug effects*
Chalcones / chemical synthesis*
Chalcones / chemistry
Chalcones / pharmacology*
Cycloaddition Reaction
Drug Design
Female
HeLa Cells
Humans
Inhibitory Concentration 50
Molecular Structure
Triazoles / chemistry*

Substances

Azides
Chalcones
Triazoles