Design, efficient synthesis and molecular docking of some novel thiazolyl-pyrazole derivatives as anticancer agents
Abstract Pyrazoles, thiazoles and fused thiazoles have been reported to possess many biological activities. 3-Methyl-5-oxo-4-(2-arylhydrazono)-4,5-dihydro-1H-pyrazole-1-carbothioamides 3a,b (obtained from the reaction of ethyl 3-oxo-2-(2-arylhydrazono)butanoates 1a,b with thiosemicarbazide) could be...
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| Format: | Article |
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BMC
2019-09-01
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| Series: | BMC Chemistry |
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| Online Access: | http://link.springer.com/article/10.1186/s13065-019-0632-5 |
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| author | Abdelwahed R. Sayed Sobhi M. Gomha Fathy M. Abdelrazek Mohamed S. Farghaly Shaimaa A. Hassan Peter Metz |
| author_facet | Abdelwahed R. Sayed Sobhi M. Gomha Fathy M. Abdelrazek Mohamed S. Farghaly Shaimaa A. Hassan Peter Metz |
| author_sort | Abdelwahed R. Sayed |
| collection | DOAJ |
| description | Abstract Pyrazoles, thiazoles and fused thiazoles have been reported to possess many biological activities. 3-Methyl-5-oxo-4-(2-arylhydrazono)-4,5-dihydro-1H-pyrazole-1-carbothioamides 3a,b (obtained from the reaction of ethyl 3-oxo-2-(2-arylhydrazono)butanoates 1a,b with thiosemicarbazide) could be transformed into a variety of thiazolyl-pyrazole derivatives 6a–h, 10a–c, 15a–c, 17, 19 and 21 via their reaction with a diversity hydrazonoyl chlorides as well as bromoacetyl derivatives. Moreover, the computational studies were carried out for all new compounds. The results indicated that five compounds showed promising binding affinities (10a: − 3.4 kcal/mol, 6d: − 3.0 kcal/mol, 15a: − 2.2 kcal/mol, 3a: − 1.6 kcal/mol, and 21: − 1.3 kcal/mol) against the active site of the epidermal growth factor receptor kinase (EGFR). The cytotoxicity of the potent products 3a, 6d, 10a, 15a, and 21 was examined against human liver carcinoma cell line (HepG-2) and revealed activities close to Doxorubicin standard drug. There was an understanding between the benefits of restricting affinities and the data obtained from the practical anticancer screening of the tested compounds. |
| first_indexed | 2024-12-23T04:34:18Z |
| format | Article |
| id | doaj.art-1534488b78d7424f91dd6ef64650e0bd |
| institution | Directory Open Access Journal |
| issn | 2661-801X |
| language | English |
| last_indexed | 2024-12-23T04:34:18Z |
| publishDate | 2019-09-01 |
| publisher | BMC |
| record_format | Article |
| series | BMC Chemistry |
| spelling | doaj.art-1534488b78d7424f91dd6ef64650e0bd2022-12-21T17:59:56ZengBMCBMC Chemistry2661-801X2019-09-0113111310.1186/s13065-019-0632-5Design, efficient synthesis and molecular docking of some novel thiazolyl-pyrazole derivatives as anticancer agentsAbdelwahed R. Sayed0Sobhi M. Gomha1Fathy M. Abdelrazek2Mohamed S. Farghaly3Shaimaa A. Hassan4Peter Metz5Department of Chemistry, Faculty of Science, King Faisal UniversityChemistry Department, Faculty of Science, Cairo UniversityChemistry Department, Faculty of Science, Cairo UniversityChemistry Department, Faculty of Science, Cairo UniversityChemistry Department, Faculty of Science, Cairo UniversityFakultat Chemie und Lebensmittelchemie, TU-DresdenAbstract Pyrazoles, thiazoles and fused thiazoles have been reported to possess many biological activities. 3-Methyl-5-oxo-4-(2-arylhydrazono)-4,5-dihydro-1H-pyrazole-1-carbothioamides 3a,b (obtained from the reaction of ethyl 3-oxo-2-(2-arylhydrazono)butanoates 1a,b with thiosemicarbazide) could be transformed into a variety of thiazolyl-pyrazole derivatives 6a–h, 10a–c, 15a–c, 17, 19 and 21 via their reaction with a diversity hydrazonoyl chlorides as well as bromoacetyl derivatives. Moreover, the computational studies were carried out for all new compounds. The results indicated that five compounds showed promising binding affinities (10a: − 3.4 kcal/mol, 6d: − 3.0 kcal/mol, 15a: − 2.2 kcal/mol, 3a: − 1.6 kcal/mol, and 21: − 1.3 kcal/mol) against the active site of the epidermal growth factor receptor kinase (EGFR). The cytotoxicity of the potent products 3a, 6d, 10a, 15a, and 21 was examined against human liver carcinoma cell line (HepG-2) and revealed activities close to Doxorubicin standard drug. There was an understanding between the benefits of restricting affinities and the data obtained from the practical anticancer screening of the tested compounds.http://link.springer.com/article/10.1186/s13065-019-0632-5Coupling reactionCyclocondensationHydrazonoyl halidesPyrazolonesAnticancer activityMolecular docking |
| spellingShingle | Abdelwahed R. Sayed Sobhi M. Gomha Fathy M. Abdelrazek Mohamed S. Farghaly Shaimaa A. Hassan Peter Metz Design, efficient synthesis and molecular docking of some novel thiazolyl-pyrazole derivatives as anticancer agents BMC Chemistry Coupling reaction Cyclocondensation Hydrazonoyl halides Pyrazolones Anticancer activity Molecular docking |
| title | Design, efficient synthesis and molecular docking of some novel thiazolyl-pyrazole derivatives as anticancer agents |
| title_full | Design, efficient synthesis and molecular docking of some novel thiazolyl-pyrazole derivatives as anticancer agents |
| title_fullStr | Design, efficient synthesis and molecular docking of some novel thiazolyl-pyrazole derivatives as anticancer agents |
| title_full_unstemmed | Design, efficient synthesis and molecular docking of some novel thiazolyl-pyrazole derivatives as anticancer agents |
| title_short | Design, efficient synthesis and molecular docking of some novel thiazolyl-pyrazole derivatives as anticancer agents |
| title_sort | design efficient synthesis and molecular docking of some novel thiazolyl pyrazole derivatives as anticancer agents |
| topic | Coupling reaction Cyclocondensation Hydrazonoyl halides Pyrazolones Anticancer activity Molecular docking |
| url | http://link.springer.com/article/10.1186/s13065-019-0632-5 |
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