| Summary: | The syntheses of novel 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinazolines <b>12</b> and 2,4-bis[(substituted-aminomethyl)phenyl]phenylquinolines <b>13</b> are reported here in six steps starting from various halogeno-quinazoline-2,4-(1<i>H</i>,3<i>H</i>)-diones or substituted anilines. The antiproliferative activities of the products were determined in vitro against a panel of breast (MCF-7 and MDA-MB-231), human adherent cervical (HeLa and SiHa), and ovarian (A2780) cell lines. Disubstituted 6- and 7-phenyl-bis(3-dimethylaminopropyl)aminomethylphenyl-quinazolines <b>12b</b>, <b>12f</b>, and <b>12i</b> displayed the most interesting antiproliferative activities against six human cancer cell lines. In the series of quinoline derivatives, 6-phenyl-bis(3-dimethylaminopropyl)aminomethylphenylquinoline <b>13a</b> proved to be the most active. G-quadruplexes (G4) stacked non-canonical nucleic acid structures found in specific G-rich DNA, or RNA sequences in the human genome are considered as potential targets for the development of anticancer agents. Then, as small aza-organic heterocyclic derivatives are well known to target and stabilize G4 structures, their ability to bind G4 structures have been determined through FRET melting, circular dichroism, and native mass spectrometry assays. Finally, telomerase inhibition ability has been also assessed using the MCF-7 cell line.
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