Synthesis and Antimicrobial, Anticancer and Anti-Oxidant Activities of Novel 2,3-Dihydropyrido[2,3-d]pyrimidine-4-one and Pyrrolo[2,1-b][1,3]benzothiazole Derivatives via Microwave-Assisted Synthesis
In our attempt towards the synthesis and development of effective antimicrobial, anticancer and antioxidant agents, a novel series of 2,3-dihydropyrido[2,3-d]pyrimidin-4-one <b>7a</b>–<b>e</b> and pyrrolo[2,1-b][1,3]benzothiazoles <b>9a</b>–<b>e</b> we...
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MDPI AG
2022-02-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/4/1246 |
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| author | Aamal A. Al-Mutairi Hend N. Hafez Abdel-Rhaman B. A. El-Gazzar Marwa Y. A. Mohamed |
| author_facet | Aamal A. Al-Mutairi Hend N. Hafez Abdel-Rhaman B. A. El-Gazzar Marwa Y. A. Mohamed |
| author_sort | Aamal A. Al-Mutairi |
| collection | DOAJ |
| description | In our attempt towards the synthesis and development of effective antimicrobial, anticancer and antioxidant agents, a novel series of 2,3-dihydropyrido[2,3-d]pyrimidin-4-one <b>7a</b>–<b>e</b> and pyrrolo[2,1-b][1,3]benzothiazoles <b>9a</b>–<b>e</b> were synthesized. The synthesis of 2-(1,3-benzo thiazol-2-yl)-3-(aryl)prop-2-enenitrile (<b>5a</b>–<b>e</b>) as the key intermediate was accomplished by a microwave efficient method. Via a new variety oriented synthetic microwave pathway, these highly functionalized building blocks allowed access to numerous fused heteroaromatic such as 7-amino-6-(1,3-benzo thiazol-2-yl)-5-(aryl)-2-thioxo-2,3dihydropyrido [2,3-d]pyrimidin-4(1H)-one <b>7a</b>–<b>e</b> and 1-amino-2-(aryl)pyrrolo[2,1-b][1,3]benzothiazole-3-carbonitrile derivatives <b>9a</b>–<b>e</b> in order to study their antimicrobial and anticancer activity. The present investigation offers effective and rapid new procedures for the synthesis of the newly polycondensed heterocyclic ring systems. All the newly synthesized compounds were evaluated for antimicrobial, anticancer and antioxidant activity. Compounds <b>7a</b>,<b>d</b>, and <b>9a</b>,<b>d</b> showed higher antimicrobial activity than cefotaxime and fluconazole while the remaining compounds exhibited good to moderate activity against bacteria and fungi. An anticancer evaluation of the newly synthesized compounds against the three tumor cell lines (lung cell NCI-H460, liver cancer HepG2 and colon cancer HCT-116) exhibited that compounds <b>7a</b>, <b>d</b>, and <b>9a</b>,<b>d</b> have higher cytotoxicity against the three human cell lines compared to doxorubicin as a reference drug. These compounds also exhibited higher antioxidant activity and a great ability to protect DNA from damage induced by bleomycin. |
| first_indexed | 2024-03-09T21:20:30Z |
| format | Article |
| id | doaj.art-19188539452440619cf0f303abf68c42 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T21:20:30Z |
| publishDate | 2022-02-01 |
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| series | Molecules |
| spelling | doaj.art-19188539452440619cf0f303abf68c422023-11-23T21:21:02ZengMDPI AGMolecules1420-30492022-02-01274124610.3390/molecules27041246Synthesis and Antimicrobial, Anticancer and Anti-Oxidant Activities of Novel 2,3-Dihydropyrido[2,3-d]pyrimidine-4-one and Pyrrolo[2,1-b][1,3]benzothiazole Derivatives via Microwave-Assisted SynthesisAamal A. Al-Mutairi0Hend N. Hafez1Abdel-Rhaman B. A. El-Gazzar2Marwa Y. A. Mohamed3Chemistry Department, Faculty of Science, Saudi Arabia; Imam Mohammad Ibn Saud Islamic University (IMSIU), P.O. Box 90950, Riyadh 11623, Saudi ArabiaHeterocyclic & Nucleosides Unit, Photochemistry Department, National Research Centre, Dokki, Giza 12622, EgyptHeterocyclic & Nucleosides Unit, Photochemistry Department, National Research Centre, Dokki, Giza 12622, EgyptBiology Department, Faculty of Science, Saudi Arabia; Imam Mohammad Ibn Saud Islamic University (IMSIU), P.O. Box 90950, Riyadh 11623, Saudi ArabiaIn our attempt towards the synthesis and development of effective antimicrobial, anticancer and antioxidant agents, a novel series of 2,3-dihydropyrido[2,3-d]pyrimidin-4-one <b>7a</b>–<b>e</b> and pyrrolo[2,1-b][1,3]benzothiazoles <b>9a</b>–<b>e</b> were synthesized. The synthesis of 2-(1,3-benzo thiazol-2-yl)-3-(aryl)prop-2-enenitrile (<b>5a</b>–<b>e</b>) as the key intermediate was accomplished by a microwave efficient method. Via a new variety oriented synthetic microwave pathway, these highly functionalized building blocks allowed access to numerous fused heteroaromatic such as 7-amino-6-(1,3-benzo thiazol-2-yl)-5-(aryl)-2-thioxo-2,3dihydropyrido [2,3-d]pyrimidin-4(1H)-one <b>7a</b>–<b>e</b> and 1-amino-2-(aryl)pyrrolo[2,1-b][1,3]benzothiazole-3-carbonitrile derivatives <b>9a</b>–<b>e</b> in order to study their antimicrobial and anticancer activity. The present investigation offers effective and rapid new procedures for the synthesis of the newly polycondensed heterocyclic ring systems. All the newly synthesized compounds were evaluated for antimicrobial, anticancer and antioxidant activity. Compounds <b>7a</b>,<b>d</b>, and <b>9a</b>,<b>d</b> showed higher antimicrobial activity than cefotaxime and fluconazole while the remaining compounds exhibited good to moderate activity against bacteria and fungi. An anticancer evaluation of the newly synthesized compounds against the three tumor cell lines (lung cell NCI-H460, liver cancer HepG2 and colon cancer HCT-116) exhibited that compounds <b>7a</b>, <b>d</b>, and <b>9a</b>,<b>d</b> have higher cytotoxicity against the three human cell lines compared to doxorubicin as a reference drug. These compounds also exhibited higher antioxidant activity and a great ability to protect DNA from damage induced by bleomycin.https://www.mdpi.com/1420-3049/27/4/1246pyrido[2,3-d]pyrimidinepyrrolo[2,1-b][1,3]benzothiazolearylidenesmicrowaveantimicrobialanticancer |
| spellingShingle | Aamal A. Al-Mutairi Hend N. Hafez Abdel-Rhaman B. A. El-Gazzar Marwa Y. A. Mohamed Synthesis and Antimicrobial, Anticancer and Anti-Oxidant Activities of Novel 2,3-Dihydropyrido[2,3-d]pyrimidine-4-one and Pyrrolo[2,1-b][1,3]benzothiazole Derivatives via Microwave-Assisted Synthesis Molecules pyrido[2,3-d]pyrimidine pyrrolo[2,1-b][1,3]benzothiazole arylidenes microwave antimicrobial anticancer |
| title | Synthesis and Antimicrobial, Anticancer and Anti-Oxidant Activities of Novel 2,3-Dihydropyrido[2,3-d]pyrimidine-4-one and Pyrrolo[2,1-b][1,3]benzothiazole Derivatives via Microwave-Assisted Synthesis |
| title_full | Synthesis and Antimicrobial, Anticancer and Anti-Oxidant Activities of Novel 2,3-Dihydropyrido[2,3-d]pyrimidine-4-one and Pyrrolo[2,1-b][1,3]benzothiazole Derivatives via Microwave-Assisted Synthesis |
| title_fullStr | Synthesis and Antimicrobial, Anticancer and Anti-Oxidant Activities of Novel 2,3-Dihydropyrido[2,3-d]pyrimidine-4-one and Pyrrolo[2,1-b][1,3]benzothiazole Derivatives via Microwave-Assisted Synthesis |
| title_full_unstemmed | Synthesis and Antimicrobial, Anticancer and Anti-Oxidant Activities of Novel 2,3-Dihydropyrido[2,3-d]pyrimidine-4-one and Pyrrolo[2,1-b][1,3]benzothiazole Derivatives via Microwave-Assisted Synthesis |
| title_short | Synthesis and Antimicrobial, Anticancer and Anti-Oxidant Activities of Novel 2,3-Dihydropyrido[2,3-d]pyrimidine-4-one and Pyrrolo[2,1-b][1,3]benzothiazole Derivatives via Microwave-Assisted Synthesis |
| title_sort | synthesis and antimicrobial anticancer and anti oxidant activities of novel 2 3 dihydropyrido 2 3 d pyrimidine 4 one and pyrrolo 2 1 b 1 3 benzothiazole derivatives via microwave assisted synthesis |
| topic | pyrido[2,3-d]pyrimidine pyrrolo[2,1-b][1,3]benzothiazole arylidenes microwave antimicrobial anticancer |
| url | https://www.mdpi.com/1420-3049/27/4/1246 |
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