Submit Manuscript  

Article Details


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

[ Vol. 16 , Issue. 2 ]

Author(s):

Zahra Tashrifi, Maryam Mohammadi-khanaposhtani, Mehdi Shafiee Ardestani, Maliheh Safavi, Kurosh Rad-Moghadam*, Morteza Mehrdad, Bagher Larijani and Mohammad Mahdavi*   Pages 213 - 219 ( 7 )

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.

Affiliation:

Department of Chemistry, University of Guilan, Rasht, Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Department of Radiopharmacy and Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Department of Biotechnology, Iranian Research Organization for Science and Technology, Tehran, Department of Chemistry, University of Guilan, Rasht, Department of Chemistry, University of Guilan, Rasht, Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran

Graphical Abstract:



Read Full-Text article