Hybrid Molecules Composed of 2,4-Diamino-1,3,5-triazines and 2-Imino-Coumarins and Coumarins. Synthesis and Cytotoxic Properties

Abstract

A series of 2-imino-2<i>H</i>-chromen-3-yl-1,3,5-triazine compounds <b>5</b>⁻<b>12</b>, which are namely hybrids of 2,4-diamino-1,3,5-triazines and 2-imino-coumarins, was synthesized by reacting 2-(4,6-diamine-1,3,5-triazin-2-yl)acetonitriles <b>1</b>⁻<b>4</b> with 2-hydroxybenzaldehydes. After this, upon heating in aqueous DMF, 2-imino-2<i>H</i>-chromen-3-yl-1,3,5-triazines <b>10</b> and <b>12</b> were converted into the corresponding 2<i>H</i>-chromen-3-yl-1,3,5-triazines <b>13</b> and <b>14</b>, which are essentially hybrids of 2,4-diamino-1,3,5-triazines and coumarins. The in vitro anticancer activity of the newly prepared compounds was evaluated against five human cancer cell lines: DAN-G, A-427, LCLC-103H, SISO and RT-4. The greatest cytotoxic activity displayed 4-[7-(diethylamino)-2-imino-2<i>H</i>-chromen-3-yl]-6-(4-phenylpiperazin-1-yl)-1,3,5-triazin-2-amine (11, IC₅₀ in the range of 1.51⁻2.60 μM).