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An efficient one-pot synthesis of 2-thioxopyrimido[4,5-<i>b</i>]quinoline <b>3a,b</b> has been accomplished from a three-component reaction of 6-aminothiouracil, cyclohexanone and aromatic aldehyde under microwave irradiation. Compound <b>3a,b</b> was used as a key intermediate for the synthesis of <i>S</i>- and <i>C</i>-nucleoside analogs of types, 5-(4-fluorophenyl / 4-anisyl)-2-<i>S</i>-(β-D-ribofuranosyl / arabinofuranosyl)-6,7,8,9-tetrahydro-3<i>H</i>-pyrimido[4,5-b]quinolin-4-one (<b>6a–d</b>) and 5-(4-fluorophenyl / 4-anisyl)-2-<i>S</i>-(β-D-gluco / galactopyranosyl)-6,7,8,9-tetrahydro-3H-pyrimido[4,5-b]quinolin-4-one (<b>8a–d</b>). Also. the 2-hydrazino compounds <b>9a,b</b> were used for the synthesis of 3-(glycosyl)-6-(4-substituted phenyl)-7,8,9,10-tetrahydro[1,2,4]triazolo[4',3':1,2]pyrimido[4,5-b]quinoline-5-(1<i>H</i>)-one (<b>11a–d</b> and <b>13a–d</b>). The title compounds were investigated for anti-inflammatory and anticancer activities. Compounds <b>11a</b> exhibited the comparable anti-inflammatory activity (83.4 %) to the standard drug Indomethacin (85.2 %). 5-(4-Fluorophenyl)-2-<i>S</i>-(β-D-ribofuranosyl)-6,7,8,9-tetrahydro-3<i>H</i>-pyrimido[4,5-b]quinolin-4-one <b>6a</b> and 3-(ribosyl)-5-(4-fluorophenyl)-7,8,9,10-tetrahydro[1,2,4]triazolo[4',3':1,2]pyrimido[4,5-b]quinolin-5-one (<b>13a</b>) exhibited the maximum cytotoxic effect against the three human cancer cell lines with inhibitory effects higher than the reference doxorubicin. <br><a rel="license" href="http://creativecommons.org/licenses/by/4.0/"><img alt="Creative Commons License" style="border-width:0" src="https://i.creativecommons.org/l/by/4.0/80x15.png" /></a> This work is licensed under a <a rel="license" href="http://creativecommons.org/licenses/by/4.0/">Creative Commons Attribution 4.0 International License</a>.