Letters in Drug Design & Discovery

Atta-ur-Rahman  , FRS
Honorary Life Fellow
Kings College
University of Cambridge
Email: lddd@benthamscience.org


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

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

Affiliation: Department of Pharmaceutical Chemistry & Pesticides Technology, School of Chemical Engineering, Hanoi University of Science and Technology, No 1 Dai Co Viet Street, Hai Ba Trung District, Hanoi, Vietnam.

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


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.

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Article Details

Page: [297 - 303]
Pages: 7
DOI: 10.2174/157018081131000073