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Synthesis and Cytotoxic Activity of Novel Poly-Substituted Imidazo[2,1-C][1,2,4]Triazin-6-Amines Publisher Pubmed



Akbarzadeh T1, 2 ; Noushini S1 ; Taban S1 ; Mahdavi M1 ; Khoshneviszadeh M3 ; Saeedi M2 ; Emami S4 ; Eghtedari M5 ; Sarrafi Y5 ; Safavi M6 ; Divsalar K7 ; Moshafi MH7 ; Asadipour A7 ; Sabourian R2 Show All Authors
Authors
  1. Akbarzadeh T1, 2
  2. Noushini S1
  3. Taban S1
  4. Mahdavi M1
  5. Khoshneviszadeh M3
  6. Saeedi M2
  7. Emami S4
  8. Eghtedari M5
  9. Sarrafi Y5
  10. Safavi M6
  11. Divsalar K7
  12. Moshafi MH7
  13. Asadipour A7
  14. Sabourian R2
  15. Edraki N3
  16. Firouzi O3
  17. Miri R3
  18. Shafiee A1
  19. Foroumadi A1, 7

Source: Molecular Diversity Published:2015


Abstract

A novel series of 3,4-diphenyl-7-(hetero)arylimidazo[2,1-$$c$$c][1,2,4]triazin-6-amine derivatives were synthesized via three-component reaction of 5,6-diphenyl-1,2,4-triazin-3-amine, various aromatic aldehydes, and cyclohexyl isocyanide. All synthesized compounds were tested against HL60 (human promyelocytic leukemia), MOLT-4 (human T lymphoblastic leukemia), and MCF-7 (human breast adenocarcinoma) cell lines, as cytotoxic agents. The structure–activity relationships study revealed that the introduction of hydroxyl and methoxy groups on the 7-phenyl ring can modulate the cytotoxic activity of these compounds. Among the 7-aryl derivatives, 3-hydroxyphenyl and 3-hydroxy-4-methoxyphenyl derivatives (6h and 6o) were the most potent compounds against HL60 and MCF-7 cells (IC50s = 9.8-20.4μM). However, the replacement of the 7-aryl moiety with pyridyl or furan-2-yl resulted in compounds 6p or 6r with more promising cytotoxicity against MOLT-4 cell line (IC50 values 12.1 and 13.0 μM, respectively). Also, the acridine orange/ethidium bromide staining assay in MCF-7 cells suggested that the cytotoxic activity of compound 6r occurs via apoptosis. © 2015, Springer International Publishing Switzerland.
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