Development of certain novel N-(2-(2-(2-oxoindolin-3-ylidene)hydrazinecarbonyl)phenyl)-benzamides and 3-(2-oxoindolin-3-ylideneamino)-2-substituted quinazolin-4(3H)-ones as CFM-1 analogs: design, synthesis, QSAR analysis and anticancer activity.
The reaction of N-(2-(hydrazinecarbonyl)aryl)benzamides 2a, b with indoline-2,3-diones 4ae in acidified ethanolic solution furnished the corresponding N-(2-(2-(2-oxoindolin-3-ylidene)hydrazinecarbonyl)phenyl)benzamides 5aj, respectively. Furthermore, 3-(2-oxoindolin-3-ylideneamino)-2-substituted qui...
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| Format: | Article |
| Language: | English English |
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Elsevier
2015
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| Online Access: | http://irep.iium.edu.my/66942/ http://irep.iium.edu.my/66942/1/Development%20of%20certain%20novel%20N-%282-%282-%282-oxoindolin-3-ylidene%29hydrazinecarbonyl%29phenyl%29-benzamides%20and%203-%282-oxoindolin-3-ylideneamino%29-2-substituted%20quinazolin-4%283H%29-ones%20as%20CFM-1%20analogs.pdf http://irep.iium.edu.my/66942/7/66942_Scopus%20-%20Document%20details.pdf |
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| author | Alafeefy, Ahmed M. Ashour, Abdelkader Elbadawy Abbas Prasad, Onkar Sinha, Leena Pathak, Shilendra Alasmari, Fatimah A. Rishi, Arun K. Abdel-Aziz, Hatem A. |
| author_facet | Alafeefy, Ahmed M. Ashour, Abdelkader Elbadawy Abbas Prasad, Onkar Sinha, Leena Pathak, Shilendra Alasmari, Fatimah A. Rishi, Arun K. Abdel-Aziz, Hatem A. |
| author_sort | Alafeefy, Ahmed M. |
| building | IIUM Repository |
| collection | Online Access |
| description | The reaction of N-(2-(hydrazinecarbonyl)aryl)benzamides 2a, b with indoline-2,3-diones 4ae in acidified ethanolic solution furnished the corresponding N-(2-(2-(2-oxoindolin-3-ylidene)hydrazinecarbonyl)phenyl)benzamides 5aj, respectively. Furthermore, 3-(2-oxoindolin-3-ylideneamino)-2-substituted quinazolin-4(3H)-ones 6aj were prepared by the reaction of 3-amino-2-arylquinazolin-4(3H)-one 3a, b with 4ae. Six derivatives of the twenty newly synthesized compounds showed remarkable antitumor activity against most of the tested cell lines, Daoy, UW228-2, Huh-7, Hela and MDA-MB231. Although these six compounds were more potent than the standard drug (CFM-1), indeed compounds 5b, 5d and 6b were the best candidates with IC50 values in the range 1.866.87, 4.4210.89 and 1.468.60 μg/ml and percentage inhibition in the range 77.188.7, 59.4184.8 and 75.488.0%, respectively. QSAR analyses on the current series of derivatives also have been performed for all five cancer cell lines and thus 10 statistically significant models were developed and internally cross validated. |
| first_indexed | 2025-11-14T17:12:43Z |
| format | Article |
| id | iium-66942 |
| institution | International Islamic University Malaysia |
| institution_category | Local University |
| language | English English |
| last_indexed | 2025-11-14T17:12:43Z |
| publishDate | 2015 |
| publisher | Elsevier |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | iium-669422019-01-04T08:54:32Z http://irep.iium.edu.my/66942/ Development of certain novel N-(2-(2-(2-oxoindolin-3-ylidene)hydrazinecarbonyl)phenyl)-benzamides and 3-(2-oxoindolin-3-ylideneamino)-2-substituted quinazolin-4(3H)-ones as CFM-1 analogs: design, synthesis, QSAR analysis and anticancer activity. Alafeefy, Ahmed M. Ashour, Abdelkader Elbadawy Abbas Prasad, Onkar Sinha, Leena Pathak, Shilendra Alasmari, Fatimah A. Rishi, Arun K. Abdel-Aziz, Hatem A. RM300 Drugs and their action The reaction of N-(2-(hydrazinecarbonyl)aryl)benzamides 2a, b with indoline-2,3-diones 4ae in acidified ethanolic solution furnished the corresponding N-(2-(2-(2-oxoindolin-3-ylidene)hydrazinecarbonyl)phenyl)benzamides 5aj, respectively. Furthermore, 3-(2-oxoindolin-3-ylideneamino)-2-substituted quinazolin-4(3H)-ones 6aj were prepared by the reaction of 3-amino-2-arylquinazolin-4(3H)-one 3a, b with 4ae. Six derivatives of the twenty newly synthesized compounds showed remarkable antitumor activity against most of the tested cell lines, Daoy, UW228-2, Huh-7, Hela and MDA-MB231. Although these six compounds were more potent than the standard drug (CFM-1), indeed compounds 5b, 5d and 6b were the best candidates with IC50 values in the range 1.866.87, 4.4210.89 and 1.468.60 μg/ml and percentage inhibition in the range 77.188.7, 59.4184.8 and 75.488.0%, respectively. QSAR analyses on the current series of derivatives also have been performed for all five cancer cell lines and thus 10 statistically significant models were developed and internally cross validated. Elsevier 2015-03-06 Article PeerReviewed application/pdf en http://irep.iium.edu.my/66942/1/Development%20of%20certain%20novel%20N-%282-%282-%282-oxoindolin-3-ylidene%29hydrazinecarbonyl%29phenyl%29-benzamides%20and%203-%282-oxoindolin-3-ylideneamino%29-2-substituted%20quinazolin-4%283H%29-ones%20as%20CFM-1%20analogs.pdf application/pdf en http://irep.iium.edu.my/66942/7/66942_Scopus%20-%20Document%20details.pdf Alafeefy, Ahmed M. and Ashour, Abdelkader Elbadawy Abbas and Prasad, Onkar and Sinha, Leena and Pathak, Shilendra and Alasmari, Fatimah A. and Rishi, Arun K. and Abdel-Aziz, Hatem A. (2015) Development of certain novel N-(2-(2-(2-oxoindolin-3-ylidene)hydrazinecarbonyl)phenyl)-benzamides and 3-(2-oxoindolin-3-ylideneamino)-2-substituted quinazolin-4(3H)-ones as CFM-1 analogs: design, synthesis, QSAR analysis and anticancer activity. European Journal of Medicinal Chemistry, 92. pp. 192-201. ISSN 0009-4374 E-ISSN 0223-5234 https://www.sciencedirect.com/journal/european-journal-of-medicinal-chemistry 10.1016/j.ejmech.2014.12.048 |
| spellingShingle | RM300 Drugs and their action Alafeefy, Ahmed M. Ashour, Abdelkader Elbadawy Abbas Prasad, Onkar Sinha, Leena Pathak, Shilendra Alasmari, Fatimah A. Rishi, Arun K. Abdel-Aziz, Hatem A. Development of certain novel N-(2-(2-(2-oxoindolin-3-ylidene)hydrazinecarbonyl)phenyl)-benzamides and 3-(2-oxoindolin-3-ylideneamino)-2-substituted quinazolin-4(3H)-ones as CFM-1 analogs: design, synthesis, QSAR analysis and anticancer activity. |
| title | Development of certain novel N-(2-(2-(2-oxoindolin-3-ylidene)hydrazinecarbonyl)phenyl)-benzamides and 3-(2-oxoindolin-3-ylideneamino)-2-substituted quinazolin-4(3H)-ones as CFM-1 analogs: design, synthesis, QSAR analysis and anticancer activity. |
| title_full | Development of certain novel N-(2-(2-(2-oxoindolin-3-ylidene)hydrazinecarbonyl)phenyl)-benzamides and 3-(2-oxoindolin-3-ylideneamino)-2-substituted quinazolin-4(3H)-ones as CFM-1 analogs: design, synthesis, QSAR analysis and anticancer activity. |
| title_fullStr | Development of certain novel N-(2-(2-(2-oxoindolin-3-ylidene)hydrazinecarbonyl)phenyl)-benzamides and 3-(2-oxoindolin-3-ylideneamino)-2-substituted quinazolin-4(3H)-ones as CFM-1 analogs: design, synthesis, QSAR analysis and anticancer activity. |
| title_full_unstemmed | Development of certain novel N-(2-(2-(2-oxoindolin-3-ylidene)hydrazinecarbonyl)phenyl)-benzamides and 3-(2-oxoindolin-3-ylideneamino)-2-substituted quinazolin-4(3H)-ones as CFM-1 analogs: design, synthesis, QSAR analysis and anticancer activity. |
| title_short | Development of certain novel N-(2-(2-(2-oxoindolin-3-ylidene)hydrazinecarbonyl)phenyl)-benzamides and 3-(2-oxoindolin-3-ylideneamino)-2-substituted quinazolin-4(3H)-ones as CFM-1 analogs: design, synthesis, QSAR analysis and anticancer activity. |
| title_sort | development of certain novel n-(2-(2-(2-oxoindolin-3-ylidene)hydrazinecarbonyl)phenyl)-benzamides and 3-(2-oxoindolin-3-ylideneamino)-2-substituted quinazolin-4(3h)-ones as cfm-1 analogs: design, synthesis, qsar analysis and anticancer activity. |
| topic | RM300 Drugs and their action |
| url | http://irep.iium.edu.my/66942/ http://irep.iium.edu.my/66942/ http://irep.iium.edu.my/66942/ http://irep.iium.edu.my/66942/1/Development%20of%20certain%20novel%20N-%282-%282-%282-oxoindolin-3-ylidene%29hydrazinecarbonyl%29phenyl%29-benzamides%20and%203-%282-oxoindolin-3-ylideneamino%29-2-substituted%20quinazolin-4%283H%29-ones%20as%20CFM-1%20analogs.pdf http://irep.iium.edu.my/66942/7/66942_Scopus%20-%20Document%20details.pdf |