Akbarzadeh T, Noushini S, Taban S, Mahdavi M, Khoshneviszadeh M, Saeedi M, Emami S, Eghtedari M, Sarrafi Y, Khoshneviszadeh M, Safavi M, Divsalar K, Moshafi MH, Asadipour A, Sabourian R, Edraki N, Firouzi O, Miri R, Shafiee A, Foroumadi A
Mol Divers. 2015;19(2):273-81 (ISI: 2.544)

A novel series of 3,4-diphenyl-7-(hetero)arylimidazo[2,1-cc][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=9.8−20.4μIC50s=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 (IC50IC50 values 12.1 and 13.0 μμM, respectively). Also, the acridine orange/ethidium bromide staining assay in MCF-7 cells suggested that the cytotoxic activity of compound 6r occurs via apoptosis.

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