Design, Synthesis and In vitro Cytotoxicity of New 1,2,3-triazol- and Nitrostyrene Hybrids as Potent Anticancer Agents

Author(s): Zahra Tashrifi, Maryam Mohammadi-khanaposhtani, Mehdi Shafiee Ardestani, Maliheh Safavi, Kurosh Rad-Moghadam*, Morteza Mehrdad, Bagher Larijani, Mohammad Mahdavi*

Journal Name: Letters in Drug Design & Discovery

Volume 16 , Issue 2 , 2019

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Graphical Abstract:


Background: A new series of 1,2,3-triazol-nitrostyrene derivatives was designed, synthesized, and evaluated for cytotoxic activity against Hep-2 and L929 cell lines.

Methods: The synthetic procedure started from the functionalization of 4-hydroxybenzaldehyde with propargyl bromide and a subsequent click reaction to give 1,2,3-triazole derivatives. Then, the reaction of the mentioned derivatives with nitromethane led to the formation of the title compounds in excellent yields.

Results: Most of the compounds exhibited better cytotoxic activity with respect to the standard drug 5-fluorouracil. Among them, (E)-1-(3,4-dichlorobenzyl)-4-((4-(2-nitrovinyl)phenoxy)methyl)-1H- 1,2,3-triazole 6i (IC50 = 4.66 ± 1.3 µM) against the Hep-2 cell line and (E)-1-(2,3-dichlorobenzoyl)- 4-((4-(2-nitrovinyl)phenoxy)methyl)-1H-1,2,3-triazole 6g (IC50 = 5.18 ± 0.8 µM) against the L929 cell line exhibited the best cytotoxic effects.

Conclusion: Moreover, the acridine orange/ethidium bromide double staining technique showed that the most potent compounds 6i and 6g could induce apoptosis in studied cancer cell lines.

Keywords: 1, 2, 3-triazol, nitrostyrene, anticancer, apoptosis, cytotoxic, hybrid.

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Year: 2019
Page: [213 - 219]
Pages: 7
DOI: 10.2174/1570180815666180427151830
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