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Croatica Chemica Acta, Vol. 89 No. 3, 2016.

Original scientific paper

https://doi.org/10.5562/cca2912

One-Pot Microwave Synthesis of Pyrimido[4,5-b]quinoline and its C- and S-Glycosides with Anti-Inflammatory and Anticancer Activities

Hend N. Hafez ; Al-Imam Mohammad Ibn Saud Islamic University (IMSIU), Faculty of Science, Department of Chemistry, P.O.Box 90950 Riyadh 11623, Kingdom of Saudi Arabia
Sami A. Al-Hussain ; Al-Imam Mohammad Ibn Saud Islamic University (IMSIU), Faculty of Science, Department of Chemistry, P.O.Box 90950 Riyadh 11623, Kingdom of Saudi Arabia
Abdel-Rhman B. A. El-Gazzar ; Al-Imam Mohammad Ibn Saud Islamic University (IMSIU), Faculty of Science, Department of Chemistry, P.O.Box 90950 Riyadh 11623, Kingdom of Saudi Arabia

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Abstract

An efficient one-pot synthesis of 2-thioxopyrimido[4,5-b]quinoline 3a,b has been accomplished from a three-component reaction of 6-aminothiouracil, cyclohexanone and aromatic aldehyde under microwave irradiation. Compound 3a,b was used as a key intermediate for the synthesis of S- and C-nucleoside analogs of types, 5-(4-fluorophenyl / 4-anisyl)-2-S-(β-D-ribofuranosyl / arabinofuranosyl)-6,7,8,9-tetrahydro-3H-pyrimido[4,5-b]quinolin-4-one (6a–d) and 5-(4-fluorophenyl / 4-anisyl)-2-S-(β-D-gluco / galactopyranosyl)-6,7,8,9-tetrahydro-3H-pyrimido[4,5-b]quinolin-4-one (8a–d). Also. the 2-hydrazino compounds 9a,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-(1H)-one (11a–d and 13a–d). The title compounds were investigated for anti-inflammatory and anticancer activities. Compounds 11a exhibited the comparable anti-inflammatory activity (83.4 %) to the standard drug Indomethacin (85.2 %). 5-(4-Fluorophenyl)-2-S-(β-D-ribofuranosyl)-6,7,8,9-tetrahydro-3H-pyrimido[4,5-b]quinolin-4-one 6a 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 (13a) exhibited the maximum cytotoxic effect against the three human cancer cell lines with inhibitory effects higher than the reference doxorubicin.

This work is licensed under a Creative Commons Attribution 4.0 International License.

Keywords

<i>C</i>-glycoside; <i>S</i>-glycoside of pyrimido[4,5-b]qinoline; anti-inflammatory and anticancer activities

Hrčak ID:

166959

URI

https://hrcak.srce.hr/166959

Publication date:

28.9.2016.

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