Triazole-linked Chalcone and Flavone Hybrid Compounds Based on AZT Exhibiting In Vitro Anti-Cancer Activity

Title:Triazole-linked Chalcone and Flavone Hybrid Compounds Based on AZT Exhibiting In Vitro Anti-Cancer Activity

Volume: 11 Issue: 3

Author(s): Nguyen Van Minh, Nguyen Le Anh, Do Thi Thao and Tran Khac Vu

Affiliation:

Keywords: AZT, anti-cancer, Click chemistry, Chalcone, Flavone, Triazole.

Abstract: The paper presents a novel synthesis of AZT modified derivatives via click chemistry. Firstly, the reaction of 2,4-dihydroxyacetophenone (1) with propargyl bromide in acetone gave intermediates 2 in 75% yield. Next, new chalcones 3a-g were obtained in 55-65% yields through the Claisen-Schmidt reaction of 2 with different aromatic aldehydes. These chalcones were then oxidatively cyclized in DMSO in the presence of I₂ to furnish new flavones 4a-g in 45-59% yields. Finally, title compounds 5a-g and 6a-g were obtained via click reaction of 3a-h and 4a-h with 3’-Azido-2’- deoxythymidine (AZT). Novel AZT derivatives 5a-g, 6a-g were evaluated for in vitro cytotoxic activity against five cell lines: MCF-7, SK-LU-1, SW480, HepG2 and P388. The result showed that most of AZT derivatives are active to five cell lines, in which compounds 5g and 5e are found to be the most potent cytotoxic activity against SK-LU-1 and P388 cell lines with IC₅₀ value of 8.63 and 9.05 µg/mL, respectively.

Cite this article as:

Minh Van Nguyen, Anh Le Nguyen, Thao Thi Do and Vu Khac Tran, Triazole-linked Chalcone and Flavone Hybrid Compounds Based on AZT Exhibiting In Vitro Anti-Cancer Activity, Letters in Drug Design & Discovery 2014; 11 (3) . https://dx.doi.org/10.2174/157018081131000073