Synthesis of bioactive quinazolin-4(3H)-one derivatives via microwave activation tailored by phase-transfer catalysis
A series of nine new 2,3-disubstituted 4(3H)-quinazolin-4-one derivatives was furnished starting from the 2-propyl-4(3H)-quinazo-line-4-one (2). The reinvestigation of the key starting quinazolinone 2 was performed under microwave irradiation (MW) and solvent-free conditions. Combination of MW and p...
Saved in:
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Sciendo
2020-06-01
|
| Series: | Acta Pharmaceutica |
| Subjects: | |
| Online Access: | https://doi.org/10.2478/acph-2020-0001 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1832573743484895232 |
|---|---|
| author | El-Badry Yaser A. El-Hashash Mahr A. Al-Ali Khalil |
| author_facet | El-Badry Yaser A. El-Hashash Mahr A. Al-Ali Khalil |
| author_sort | El-Badry Yaser A. |
| collection | DOAJ |
| description | A series of nine new 2,3-disubstituted 4(3H)-quinazolin-4-one derivatives was furnished starting from the 2-propyl-4(3H)-quinazo-line-4-one (2). The reinvestigation of the key starting quinazolinone 2 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 N-alkylation and condensation reactions of compound 2 as a simple, efficient and eco-friendly technique. The structure of the synthesized compounds was elucidated using different spectral and chemical analyses. In vitro 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(4H)-yl)methyl]benzoate (3c), 3-{2-[6-(pyrrolidin-1-yl-sulfonyl)-1,2,3,4-tetrahydroquinoline]-2-oxoethyl}-2-propylquinazolin--4(3H)-one (3e), N’-[(E)-(2H-1,3-benzodioxo-5-yl)methylidene]-2-(4-oxo-2-propylquinazolin-3(4H)-yl)acetohydrazide (10a), N’-[(E)-(4-hydroxyphenyl)methylidene]-2-(4-oxo-2-propylquinazo-lin-3(4H) -yl)acetohydrazide (10b) and N’-[(E)-(4-nitrophenyl)methyl idene]-2-(4-oxo-2-propylquinazolin-3(4H)-yl)acetohydrazide (10c). |
| format | Article |
| id | doaj-art-2261fc1ce54c41c4b34ed7f91261908f |
| institution | Kabale University |
| issn | 1846-9558 |
| language | English |
| publishDate | 2020-06-01 |
| publisher | Sciendo |
| record_format | Article |
| series | Acta Pharmaceutica |
| spelling | doaj-art-2261fc1ce54c41c4b34ed7f91261908f2025-02-02T02:50:42ZengSciendoActa Pharmaceutica1846-95582020-06-0170216117810.2478/acph-2020-0001acph-2020-0001Synthesis of bioactive quinazolin-4(3H)-one derivatives via microwave activation tailored by phase-transfer catalysisEl-Badry Yaser A.0El-Hashash Mahr A.1Al-Ali Khalil2Organic Chemistry Laboratory, Faculty of Specific Education, Ain Shams University, Abbasseya 11566, Cairo, EgyptOrganic Chemistry Department Faculty of Science, Ain Shams University, Abbasseya 11566Cairo, EgyptMedical Laboratory Technology, Department, College of Applied Medical Sciences, Taibah University, Madinah30001 Kingdom of Saudi ArabiaA series of nine new 2,3-disubstituted 4(3H)-quinazolin-4-one derivatives was furnished starting from the 2-propyl-4(3H)-quinazo-line-4-one (2). The reinvestigation of the key starting quinazolinone 2 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 N-alkylation and condensation reactions of compound 2 as a simple, efficient and eco-friendly technique. The structure of the synthesized compounds was elucidated using different spectral and chemical analyses. In vitro 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(4H)-yl)methyl]benzoate (3c), 3-{2-[6-(pyrrolidin-1-yl-sulfonyl)-1,2,3,4-tetrahydroquinoline]-2-oxoethyl}-2-propylquinazolin--4(3H)-one (3e), N’-[(E)-(2H-1,3-benzodioxo-5-yl)methylidene]-2-(4-oxo-2-propylquinazolin-3(4H)-yl)acetohydrazide (10a), N’-[(E)-(4-hydroxyphenyl)methylidene]-2-(4-oxo-2-propylquinazo-lin-3(4H) -yl)acetohydrazide (10b) and N’-[(E)-(4-nitrophenyl)methyl idene]-2-(4-oxo-2-propylquinazolin-3(4H)-yl)acetohydrazide (10c).https://doi.org/10.2478/acph-2020-0001solid-liquid transfer catalysismicrowave-assisted reaction2-propylquinazolinonen-alkylation2, 3-disubstituted quinazolinonesanticancer activity |
| spellingShingle | El-Badry Yaser A. El-Hashash Mahr A. Al-Ali Khalil Synthesis of bioactive quinazolin-4(3H)-one derivatives via microwave activation tailored by phase-transfer catalysis Acta Pharmaceutica solid-liquid transfer catalysis microwave-assisted reaction 2-propylquinazolinone n-alkylation 2, 3-disubstituted quinazolinones anticancer activity |
| 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 3h one derivatives via microwave activation tailored by phase transfer catalysis |
| topic | solid-liquid transfer catalysis microwave-assisted reaction 2-propylquinazolinone n-alkylation 2, 3-disubstituted quinazolinones anticancer activity |
| url | https://doi.org/10.2478/acph-2020-0001 |
| work_keys_str_mv | AT elbadryyasera synthesisofbioactivequinazolin43honederivativesviamicrowaveactivationtailoredbyphasetransfercatalysis AT elhashashmahra synthesisofbioactivequinazolin43honederivativesviamicrowaveactivationtailoredbyphasetransfercatalysis AT alalikhalil synthesisofbioactivequinazolin43honederivativesviamicrowaveactivationtailoredbyphasetransfercatalysis |