Synthesis and antiproliferative activity of triazenoindazoles and triazenopyrazoles: a comparative study.
Several triazenoindazoles and triazenopyrazoles were prepared transforming the appropriate aminoindazoles and aminopyrazoles in the corresponding diazonium salts which were reacted with dimethylamine, diethylamine and pyrrolidine. All the triazenes were tested for their antiproliferative activity against K562, HL60, L1210 and MCF7 cell lines. The biological data showed that the benzocondensation plays a positive role on the antiproliferative activity. The (1)H-NMR spectra showed that the rotational barrier around the N(2)-N(3) bond in the triazene group can be influenced both by the position of this group in the indazole nucleus and by the substitution pattern in the benzene moiety.
Daidone
Giuseppe
G
Dipartimento di Chimica e Tecnologie Farmaceutiche, Università degli Studi di Palermo, via Archirafi 32, 90123 Palermo, Italy. gdaidone@unipa.it
Raffa
Demetrio
D
Maggio
Benedetta
B
Valeria Raimondi
Maria
M
Plescia
Fabiana
F
Schillaci
Domenico
D
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002455:Cell Division / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007191:Indazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011720:Pyrazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014226:Triazenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D007191:Indazoles; D011720:Pyrazoles; D014226:Triazenes