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Synthesis of bioactive quinazolin-4(3H)-one derivatives via microwave activation tailored by phase-transfer catalysis
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| Zeitschriftentitel: | Acta Pharmaceutica |
|---|---|
| Personen und Körperschaften: | , , |
| In: | Acta Pharmaceutica, 70, 2020, 2, S. 161-178 |
| Format: | E-Article |
| Sprache: | Englisch |
| veröffentlicht: |
Walter de Gruyter GmbH
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| Schlagwörter: |
| author_facet |
El-Badry, Yaser A. El-Hashash, Mahr A. Al-Ali, Khalil El-Badry, Yaser A. El-Hashash, Mahr A. Al-Ali, Khalil |
|---|---|
| author |
El-Badry, Yaser A. El-Hashash, Mahr A. Al-Ali, Khalil |
| spellingShingle |
El-Badry, Yaser A. El-Hashash, Mahr A. Al-Ali, Khalil Acta Pharmaceutica Synthesis of bioactive quinazolin-4(3H)-one derivatives via microwave activation tailored by phase-transfer catalysis Pharmaceutical Science Pharmacology General Medicine |
| author_sort |
el-badry, yaser a. |
| spelling |
El-Badry, Yaser A. El-Hashash, Mahr A. Al-Ali, Khalil 1846-9558 Walter de Gruyter GmbH Pharmaceutical Science Pharmacology General Medicine http://dx.doi.org/10.2478/acph-2020-0001 <jats:title>Abstract</jats:title> <jats:p>A series of nine new 2,3-disubstituted 4(3<jats:italic>H</jats:italic>)-quinazolin-4-one derivatives was furnished starting from the 2-propyl-4(3<jats:italic>H</jats:italic>)-quinazo-line-4-one (<jats:bold>2</jats:bold>). The reinvestigation of the key starting quinazolinone <jats:bold>2</jats:bold> was performed under microwave irradiation (MW) and solvent-free conditions. Combination of MW and phase-transfer catalysis using tetrabutylammonium benzoate (TBAB) as a novel neutral ionic catalyst was used for carrying out <jats:italic>N</jats:italic>-alkylation and condensation reactions of compound <jats:bold>2</jats:bold> as a simple, efficient and eco-friendly technique. The structure of the synthesized compounds was elucidated using different spectral and chemical analyses. <jats:italic>In vitro</jats:italic> antimicrobial activity of the compounds was investigated against four bacterial and two fungal strains; very modest activity was achieved. Some of the synthesized compounds were screened for their antitumor activity against different human tumor cell lines. The screened compounds exhibited a significant antitumor activity on some of the cancer cell lines, melanoma (SK-MEL-2), ovarian cancer (IGROV1), renal cancer (TK-10), prostate cancer (PC-3), breast cancer (MCF7) and colon cancer (HT29). The most active, even more active than the reference 5-fluorouracil, were found to be ethyl 4-[(4-oxo-2-propylquinazolin-3(4<jats:italic>H</jats:italic>)-yl)methyl]benzoate (<jats:bold>3c</jats:bold>), 3-{2-[6-(pyrrolidin-1-yl-sulfonyl)-1,2,3,4-tetrahydroquinoline]-2-oxoethyl}-2-propylquinazolin--4(3<jats:italic>H</jats:italic>)-one (<jats:bold>3e</jats:bold>), <jats:italic>N’</jats:italic>-[(<jats:italic>E</jats:italic>)-(2<jats:italic>H</jats:italic>-1,3-benzodioxo-5-yl)methylidene]-2-(4-oxo-2-propylquinazolin-3(4<jats:italic>H</jats:italic>)-yl)acetohydrazide (<jats:bold>10a</jats:bold>), <jats:italic>N’</jats:italic>-[(<jats:italic>E</jats:italic>)-(4-hydroxyphenyl)methylidene]-2-(4-oxo-2-propylquinazo-lin-3(4<jats:italic>H</jats:italic>) -yl)acetohydrazide (<jats:bold>10b</jats:bold>) and <jats:italic>N’</jats:italic>-[(<jats:italic>E</jats:italic>)-(4-nitrophenyl)methyl idene]-2-(4-oxo-2-propylquinazolin-3(4<jats:italic>H</jats:italic>)-yl)acetohydrazide (<jats:bold>10c</jats:bold>).</jats:p> Synthesis of bioactive quinazolin-4(3<i>H</i>)-one derivatives <i>via</i> microwave activation tailored by phase-transfer catalysis Acta Pharmaceutica |
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Chemie und Pharmazie |
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| title |
Synthesis of bioactive quinazolin-4(3H)-one derivatives via microwave activation tailored by phase-transfer catalysis |
| title_unstemmed |
Synthesis of bioactive quinazolin-4(3H)-one derivatives via microwave activation tailored by phase-transfer catalysis |
| title_full |
Synthesis of bioactive quinazolin-4(3H)-one derivatives via microwave activation tailored by phase-transfer catalysis |
| title_fullStr |
Synthesis of bioactive quinazolin-4(3H)-one derivatives via microwave activation tailored by phase-transfer catalysis |
| title_full_unstemmed |
Synthesis of bioactive quinazolin-4(3H)-one derivatives via microwave activation tailored by phase-transfer catalysis |
| title_short |
Synthesis of bioactive quinazolin-4(3H)-one derivatives via microwave activation tailored by phase-transfer catalysis |
| title_sort |
synthesis of bioactive quinazolin-4(3<i>h</i>)-one derivatives <i>via</i> microwave activation tailored by phase-transfer catalysis |
| topic |
Pharmaceutical Science Pharmacology General Medicine |
| url |
http://dx.doi.org/10.2478/acph-2020-0001 |
| publishDate |
2020 |
| physical |
161-178 |
| description |
<jats:title>Abstract</jats:title>
<jats:p>A series of nine new 2,3-disubstituted 4(3<jats:italic>H</jats:italic>)-quinazolin-4-one derivatives was furnished starting from the 2-propyl-4(3<jats:italic>H</jats:italic>)-quinazo-line-4-one (<jats:bold>2</jats:bold>). The reinvestigation of the key starting quinazolinone <jats:bold>2</jats:bold> was performed under microwave irradiation (MW) and solvent-free conditions. Combination of MW and phase-transfer catalysis using tetrabutylammonium benzoate (TBAB) as a novel neutral ionic catalyst was used for carrying out <jats:italic>N</jats:italic>-alkylation and condensation reactions of compound <jats:bold>2</jats:bold> as a simple, efficient and eco-friendly technique. The structure of the synthesized compounds was elucidated using different spectral and chemical analyses. <jats:italic>In vitro</jats:italic> antimicrobial activity of the compounds was investigated against four bacterial and two fungal strains; very modest activity was achieved. Some of the synthesized compounds were screened for their antitumor activity against different human tumor cell lines. The screened compounds exhibited a significant antitumor activity on some of the cancer cell lines, melanoma (SK-MEL-2), ovarian cancer (IGROV1), renal cancer (TK-10), prostate cancer (PC-3), breast cancer (MCF7) and colon cancer (HT29). The most active, even more active than the reference 5-fluorouracil, were found to be ethyl 4-[(4-oxo-2-propylquinazolin-3(4<jats:italic>H</jats:italic>)-yl)methyl]benzoate (<jats:bold>3c</jats:bold>), 3-{2-[6-(pyrrolidin-1-yl-sulfonyl)-1,2,3,4-tetrahydroquinoline]-2-oxoethyl}-2-propylquinazolin--4(3<jats:italic>H</jats:italic>)-one (<jats:bold>3e</jats:bold>), <jats:italic>N’</jats:italic>-[(<jats:italic>E</jats:italic>)-(2<jats:italic>H</jats:italic>-1,3-benzodioxo-5-yl)methylidene]-2-(4-oxo-2-propylquinazolin-3(4<jats:italic>H</jats:italic>)-yl)acetohydrazide (<jats:bold>10a</jats:bold>), <jats:italic>N’</jats:italic>-[(<jats:italic>E</jats:italic>)-(4-hydroxyphenyl)methylidene]-2-(4-oxo-2-propylquinazo-lin-3(4<jats:italic>H</jats:italic>) -yl)acetohydrazide (<jats:bold>10b</jats:bold>) and <jats:italic>N’</jats:italic>-[(<jats:italic>E</jats:italic>)-(4-nitrophenyl)methyl idene]-2-(4-oxo-2-propylquinazolin-3(4<jats:italic>H</jats:italic>)-yl)acetohydrazide (<jats:bold>10c</jats:bold>).</jats:p> |
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| author | El-Badry, Yaser A., El-Hashash, Mahr A., Al-Ali, Khalil |
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| description | <jats:title>Abstract</jats:title> <jats:p>A series of nine new 2,3-disubstituted 4(3<jats:italic>H</jats:italic>)-quinazolin-4-one derivatives was furnished starting from the 2-propyl-4(3<jats:italic>H</jats:italic>)-quinazo-line-4-one (<jats:bold>2</jats:bold>). The reinvestigation of the key starting quinazolinone <jats:bold>2</jats:bold> was performed under microwave irradiation (MW) and solvent-free conditions. Combination of MW and phase-transfer catalysis using tetrabutylammonium benzoate (TBAB) as a novel neutral ionic catalyst was used for carrying out <jats:italic>N</jats:italic>-alkylation and condensation reactions of compound <jats:bold>2</jats:bold> as a simple, efficient and eco-friendly technique. The structure of the synthesized compounds was elucidated using different spectral and chemical analyses. <jats:italic>In vitro</jats:italic> antimicrobial activity of the compounds was investigated against four bacterial and two fungal strains; very modest activity was achieved. Some of the synthesized compounds were screened for their antitumor activity against different human tumor cell lines. The screened compounds exhibited a significant antitumor activity on some of the cancer cell lines, melanoma (SK-MEL-2), ovarian cancer (IGROV1), renal cancer (TK-10), prostate cancer (PC-3), breast cancer (MCF7) and colon cancer (HT29). The most active, even more active than the reference 5-fluorouracil, were found to be ethyl 4-[(4-oxo-2-propylquinazolin-3(4<jats:italic>H</jats:italic>)-yl)methyl]benzoate (<jats:bold>3c</jats:bold>), 3-{2-[6-(pyrrolidin-1-yl-sulfonyl)-1,2,3,4-tetrahydroquinoline]-2-oxoethyl}-2-propylquinazolin--4(3<jats:italic>H</jats:italic>)-one (<jats:bold>3e</jats:bold>), <jats:italic>N’</jats:italic>-[(<jats:italic>E</jats:italic>)-(2<jats:italic>H</jats:italic>-1,3-benzodioxo-5-yl)methylidene]-2-(4-oxo-2-propylquinazolin-3(4<jats:italic>H</jats:italic>)-yl)acetohydrazide (<jats:bold>10a</jats:bold>), <jats:italic>N’</jats:italic>-[(<jats:italic>E</jats:italic>)-(4-hydroxyphenyl)methylidene]-2-(4-oxo-2-propylquinazo-lin-3(4<jats:italic>H</jats:italic>) -yl)acetohydrazide (<jats:bold>10b</jats:bold>) and <jats:italic>N’</jats:italic>-[(<jats:italic>E</jats:italic>)-(4-nitrophenyl)methyl idene]-2-(4-oxo-2-propylquinazolin-3(4<jats:italic>H</jats:italic>)-yl)acetohydrazide (<jats:bold>10c</jats:bold>).</jats:p> |
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| spelling | El-Badry, Yaser A. El-Hashash, Mahr A. Al-Ali, Khalil 1846-9558 Walter de Gruyter GmbH Pharmaceutical Science Pharmacology General Medicine http://dx.doi.org/10.2478/acph-2020-0001 <jats:title>Abstract</jats:title> <jats:p>A series of nine new 2,3-disubstituted 4(3<jats:italic>H</jats:italic>)-quinazolin-4-one derivatives was furnished starting from the 2-propyl-4(3<jats:italic>H</jats:italic>)-quinazo-line-4-one (<jats:bold>2</jats:bold>). The reinvestigation of the key starting quinazolinone <jats:bold>2</jats:bold> was performed under microwave irradiation (MW) and solvent-free conditions. Combination of MW and phase-transfer catalysis using tetrabutylammonium benzoate (TBAB) as a novel neutral ionic catalyst was used for carrying out <jats:italic>N</jats:italic>-alkylation and condensation reactions of compound <jats:bold>2</jats:bold> as a simple, efficient and eco-friendly technique. The structure of the synthesized compounds was elucidated using different spectral and chemical analyses. <jats:italic>In vitro</jats:italic> antimicrobial activity of the compounds was investigated against four bacterial and two fungal strains; very modest activity was achieved. Some of the synthesized compounds were screened for their antitumor activity against different human tumor cell lines. The screened compounds exhibited a significant antitumor activity on some of the cancer cell lines, melanoma (SK-MEL-2), ovarian cancer (IGROV1), renal cancer (TK-10), prostate cancer (PC-3), breast cancer (MCF7) and colon cancer (HT29). The most active, even more active than the reference 5-fluorouracil, were found to be ethyl 4-[(4-oxo-2-propylquinazolin-3(4<jats:italic>H</jats:italic>)-yl)methyl]benzoate (<jats:bold>3c</jats:bold>), 3-{2-[6-(pyrrolidin-1-yl-sulfonyl)-1,2,3,4-tetrahydroquinoline]-2-oxoethyl}-2-propylquinazolin--4(3<jats:italic>H</jats:italic>)-one (<jats:bold>3e</jats:bold>), <jats:italic>N’</jats:italic>-[(<jats:italic>E</jats:italic>)-(2<jats:italic>H</jats:italic>-1,3-benzodioxo-5-yl)methylidene]-2-(4-oxo-2-propylquinazolin-3(4<jats:italic>H</jats:italic>)-yl)acetohydrazide (<jats:bold>10a</jats:bold>), <jats:italic>N’</jats:italic>-[(<jats:italic>E</jats:italic>)-(4-hydroxyphenyl)methylidene]-2-(4-oxo-2-propylquinazo-lin-3(4<jats:italic>H</jats:italic>) -yl)acetohydrazide (<jats:bold>10b</jats:bold>) and <jats:italic>N’</jats:italic>-[(<jats:italic>E</jats:italic>)-(4-nitrophenyl)methyl idene]-2-(4-oxo-2-propylquinazolin-3(4<jats:italic>H</jats:italic>)-yl)acetohydrazide (<jats:bold>10c</jats:bold>).</jats:p> Synthesis of bioactive quinazolin-4(3<i>H</i>)-one derivatives <i>via</i> microwave activation tailored by phase-transfer catalysis Acta Pharmaceutica |
| spellingShingle | El-Badry, Yaser A., El-Hashash, Mahr A., Al-Ali, Khalil, Acta Pharmaceutica, Synthesis of bioactive quinazolin-4(3H)-one derivatives via microwave activation tailored by phase-transfer catalysis, Pharmaceutical Science, Pharmacology, General Medicine |
| title | Synthesis of bioactive quinazolin-4(3H)-one derivatives via microwave activation tailored by phase-transfer catalysis |
| title_full | Synthesis of bioactive quinazolin-4(3H)-one derivatives via microwave activation tailored by phase-transfer catalysis |
| title_fullStr | Synthesis of bioactive quinazolin-4(3H)-one derivatives via microwave activation tailored by phase-transfer catalysis |
| title_full_unstemmed | Synthesis of bioactive quinazolin-4(3H)-one derivatives via microwave activation tailored by phase-transfer catalysis |
| title_short | Synthesis of bioactive quinazolin-4(3H)-one derivatives via microwave activation tailored by phase-transfer catalysis |
| title_sort | synthesis of bioactive quinazolin-4(3<i>h</i>)-one derivatives <i>via</i> microwave activation tailored by phase-transfer catalysis |
| title_unstemmed | Synthesis of bioactive quinazolin-4(3H)-one derivatives via microwave activation tailored by phase-transfer catalysis |
| topic | Pharmaceutical Science, Pharmacology, General Medicine |
| url | http://dx.doi.org/10.2478/acph-2020-0001 |