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Design, Synthesis and in Vitro Cytotoxicity of New 1,2,3-Triazol-And Nitrostyrene Hybrids As Potent Anticancer Agents Publisher



Tashrifi Z1 ; Mohammadikhanaposhtani M2 ; Ardestani MS3 ; Safavi M4 ; Radmoghadam K1 ; Mehrdad M1 ; Larijani B5 ; Mahdavi M5
Authors
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Authors Affiliations
  1. 1. Department of Chemistry, University of Guilan, Rasht, Iran
  2. 2. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Iran
  3. 3. Department of Radiopharmacy and Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  4. 4. Department of Biotechnology, Iranian Research Organization for Science and Technology, Tehran, Iran
  5. 5. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran

Source: Letters in Drug Design and Discovery Published:2018


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 (IC 50 = 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 (IC 50 = 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. © 2019 Bentham Science Publishers.
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