Find in Library

The appropriate 1-arylhydrazinecarbonitriles <b>1a–c</b> are subjected to the reaction with 2-chloro-4,5-dihydro-1<i>H</i>-imidazole (<b>2</b>), yielding 7-(4,5-dihydro-1<i>H</i>-imidazol-2-yl)-2-aryl-6,7-dihydro-2<i>H</i>-imidazo[2,1-<i>c</i>][1,2,4]triazol-3(5<i>H</i>)-imines <b>3a–c</b>, which are subsequently converted into the corresponding amides <b>4a–e</b>, <b>8a–c</b>, sulfonamides <b>5a–n</b>, <b>9</b>, ureas <b>6a–I</b>, and thioureas <b>7a–d</b>. The structures of the newly prepared derivatives <b>3a–c</b>, <b>4a–e</b>, <b>5a–n</b>, <b>6a–i</b>, <b>7a–d</b>, <b>8a–c</b>, and <b>9</b> are confirmed by IR, NMR spectroscopic data, as well as single-crystal X-ray analyses of <b>5e</b> and <b>8c</b>. The in vitro cytotoxic potency of these compounds is determined on a panel of human cancer cell lines, and the relationships between structure and antitumor activity are discussed. The most active 4-chloro-<i>N</i>-(2-(4-chlorophenyl)-7-(4,5-dihydro-1<i>H</i>-imidazol-2-yl)-6,7-dihydro-2<i>H</i>-imidazo[2,1-<i>c</i>][1,2,4]triazol-3(5<i>H</i>)-ylidene)benzamide (<b>4e</b>) and <i>N</i>-(7-(4,5-dihydro-1<i>H</i>-imidazol-2-yl)-2-(<i>p</i>-tolyl)-6,7-dihydro-2<i>H</i>-imidazo[2,1-<i>c</i>][1,2,4]triazol-3(5<i>H</i>)-ylidene)-[1,1′-biphenyl]-4-sulfonamide (<b>5l</b>) inhibits the growth of the cervical cancer SISO and bladder cancer RT-112 cell lines with IC₅₀ values in the range of 2.38–3.77 μM. Moreover, <i>N</i>-(7-(4,5-dihydro-1<i>H</i>-imidazol-2-yl)-2-phenyl-6,7-dihydro-2<i>H</i>-imidazo[2,1-<i>c</i>][1,2,4]triazol-3(5<i>H</i>)-ylidene)-4-phenoxybenzenesulfonamide (<b>5m</b>) has the best selectivity towards the SISO cell line and induces apoptosis in this cell line.