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In this article, we showed the synthesis of new polycyclic aromatic compounds, such as thienotriazolopyrimidinones, <i>N</i>-(thienotriazolopyrimidine) acetamide, 2-mercapto-thienotriazolo-pyrimidinones, 2-(((thieno-triazolopyrimidine) methyl) thio) thieno-triazolopyrimidines, thieno-pyrimidotriazolo-thiazines, pyrrolo-triazolo-thienopyrimidines, thienopyrimido-triazolopyrrolo-quinoxalines, thienopyrimido-triazolo-pyrrolo-oxathiino-quinoxalinones, 1,4-oxathiino-pyrrolo- triazolothienopyrimidinones, imidazopyrrolotriazolothienopyrimidines and 1,2,4-triazoloimidazo- pyrrolotriazolothienopyrimidindiones, based on the starting material 2,3-diamino-6-benzoyl-5- methylthieno[2,3-d]pyrimidin-4(3<i>H</i>)-one (<b>3</b>). The chemical structures were confirmed using many spectroscopic ways (IR, ¹H, ¹³C, −NMR and MS) and elemental analyses. A series of thiazine, imidazole, pyrrole, thienotriazolopyrimidine derivatives were synthesized and evaluated for their antiproliferative activity against four human cancer cell lines, i.e., <b>CNE2</b> (nasopharyngeal), <b>KB</b> (oral), <b>MCF-7</b> (breast) and <b>MGC-803</b> (gastric) carcinoma cells. The compounds <b>20</b>, <b>19</b>, <b>17</b>, <b>16</b> and <b>11</b> showed significant cytotoxicity against types of human cancer cell lines.