The evaluation of the cytotoxic properties in vitro of three synthetic tripods containing pyrazole: N,N-bis[(3,5-dimethylpyrazol-1-yl)methyl]aniline (1); N,N-tetrakis[(3,5-dimethylpyrazol-1-yl)methyl]-para-phenylenediamine (2); and N,N-tetrakis-[(1,5-dimethylpyrazol-3-yl)methyl]-para-phenylenediamine (3), was examined for their cytotoxic activity on two tumor cell lines: P815 (murin mastocytoma) and Hep (human laryngeal carcinome). While the compound 2 shows a small cytotoxic activity, compounds 1 and 3 are more cytotoxic against both cell lines. However, this cytotoxicity is more pronounced against Hep cell line (IC50: 3.25 microg mL(-1) for compound 1 and 6.92 microg mL(-1) for compound 3) than P815 cell line (IC50: 17.82 microg mL(-1) for compound 1 and 37.21 microg mL(-1) for compound 3). Statistical analysis shows that the compound 1 is two- to threefold more cytotoxic than compound 3 (P < 0.05). Interestingly, the cytotoxicity induced by compound 1 against Hep cell line is more important than that induced by adriamycin used as a positive control.

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A mixture of 5,5'-diphenyl-3,3'-bipyrazole 1 (143 mg, 0.5 mmol) [1] and potassium tert-butoxide (112 mg, 1 mmol) in 20 mL of dry THF was stirred under reflux for 30 min [2]. After cooling the mixture to 0°C, the benzylbromide (171 mg, 1 mmol) in THF (5 mL) was then added drop by drop. After stirring under reflux for 3 h, the mixture was filtered and evaporated. The residue was purified on silica column (CH 2 Cl 2 ) and recrystallized from ethanol, to give product 2 (0.17g, 73 % yield) as a white solid. References and otes:Molbank 2006