Synthesis of novel thiazole, pyranothiazole, thiazolo[4,5-b]pyridines and thiazolo[5′,4′:5,6]pyrano[2,3-d]pyrimidine derivatives and incorporating isoindoline-1,3-dione group
Abstract Background Thiazole is a core structural motif presents in a wide range of natural products. Thiazole derivatives also have a wide range of medicinal and biological properties. Results The reaction of hydrazonoyl halides with 2-(1-(4-(1,3-dioxoisoindolin-2-yl)phenyl)ethylidene)hydrazinecarb...
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| Format: | Article |
| Language: | English |
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BMC
2019-03-01
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| Series: | BMC Chemistry |
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| Online Access: | http://link.springer.com/article/10.1186/s13065-019-0559-x |
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| author | Mona A. Hosny Yasser H. Zaki Wafaa A. Mokbel Abdou O. Abdelhamid |
| author_facet | Mona A. Hosny Yasser H. Zaki Wafaa A. Mokbel Abdou O. Abdelhamid |
| author_sort | Mona A. Hosny |
| collection | DOAJ |
| description | Abstract Background Thiazole is a core structural motif presents in a wide range of natural products. Thiazole derivatives also have a wide range of medicinal and biological properties. Results The reaction of hydrazonoyl halides with 2-(1-(4-(1,3-dioxoisoindolin-2-yl)phenyl)ethylidene)hydrazinecarbothioamidein ethanol and triethylamine yielded 2-(4-(1-(2-(4-(2-Arylhydrazono)-5-s-4,5-dihydrothiazol-2-yl)hydrazono)-ethyl)phenyl)isoindoline-1,3-dione and 2-(4-(1-(2-(5-(2-Arylhydrazono)-4-oxo-4,5-dihydrothiazol-2-yl)hydrazono)ethyl)-phenyl)isoindoline-1,3-dione.The reaction of 2-(4-(1-(2-(4-oxo-4,5-dihydrothiazol-2-yl)hydrazono)ethyl)phenyl)isoindoline-1,3-dione with arylidenemalononitrile also yielded 5-amino-2-(2-(1-(4-(1,3-dioxoisoindolin-2-yl)phenyl)ethylidene)hydrazinyl)-7-substituted-7H-pyrano[2,3-d]thiazole-6-carbonitrile. The structures of the newly synthesized compound were elucidated whenever possible on the basis of elemental analysis, spectral data, and alternative synthetic routes. Three of them were evaluated against a breast cancer cell line for their antitumor activity. Conclusions Compound (1) has been shown to be useful in the synthesis of a new series of 1,3-thiazole, pyrano[2,3-d]thiazole and 4,5-dihydrothiazolo[4,5-b]pyridine derivatives using hydrazonoyl halides as precursors. The anticancer efficacy of compounds (9b), (9e), and (9f) against MCF-7, a breast cancer cell line, was also compared to the standard anticancer drug doxorubicin. |
| first_indexed | 2024-12-19T10:08:05Z |
| format | Article |
| id | doaj.art-32e8712f52244798a1a64f4965897482 |
| institution | Directory Open Access Journal |
| issn | 2661-801X |
| language | English |
| last_indexed | 2024-12-19T10:08:05Z |
| publishDate | 2019-03-01 |
| publisher | BMC |
| record_format | Article |
| series | BMC Chemistry |
| spelling | doaj.art-32e8712f52244798a1a64f49658974822022-12-21T20:26:26ZengBMCBMC Chemistry2661-801X2019-03-0113111010.1186/s13065-019-0559-xSynthesis of novel thiazole, pyranothiazole, thiazolo[4,5-b]pyridines and thiazolo[5′,4′:5,6]pyrano[2,3-d]pyrimidine derivatives and incorporating isoindoline-1,3-dione groupMona A. Hosny0Yasser H. Zaki1Wafaa A. Mokbel2Abdou O. Abdelhamid3Department of Chemistry, Faculty of Women for Arts, Science and Education, Ain Shams UniversityDepartment of Chemistry, Faculty of Science, Beni-Suef UniversityDepartment of Chemistry, Faculty of Women for Arts, Science and Education, Ain Shams UniversityDepartment of Chemistry, Faculty of Science, Cairo UniversityAbstract Background Thiazole is a core structural motif presents in a wide range of natural products. Thiazole derivatives also have a wide range of medicinal and biological properties. Results The reaction of hydrazonoyl halides with 2-(1-(4-(1,3-dioxoisoindolin-2-yl)phenyl)ethylidene)hydrazinecarbothioamidein ethanol and triethylamine yielded 2-(4-(1-(2-(4-(2-Arylhydrazono)-5-s-4,5-dihydrothiazol-2-yl)hydrazono)-ethyl)phenyl)isoindoline-1,3-dione and 2-(4-(1-(2-(5-(2-Arylhydrazono)-4-oxo-4,5-dihydrothiazol-2-yl)hydrazono)ethyl)-phenyl)isoindoline-1,3-dione.The reaction of 2-(4-(1-(2-(4-oxo-4,5-dihydrothiazol-2-yl)hydrazono)ethyl)phenyl)isoindoline-1,3-dione with arylidenemalononitrile also yielded 5-amino-2-(2-(1-(4-(1,3-dioxoisoindolin-2-yl)phenyl)ethylidene)hydrazinyl)-7-substituted-7H-pyrano[2,3-d]thiazole-6-carbonitrile. The structures of the newly synthesized compound were elucidated whenever possible on the basis of elemental analysis, spectral data, and alternative synthetic routes. Three of them were evaluated against a breast cancer cell line for their antitumor activity. Conclusions Compound (1) has been shown to be useful in the synthesis of a new series of 1,3-thiazole, pyrano[2,3-d]thiazole and 4,5-dihydrothiazolo[4,5-b]pyridine derivatives using hydrazonoyl halides as precursors. The anticancer efficacy of compounds (9b), (9e), and (9f) against MCF-7, a breast cancer cell line, was also compared to the standard anticancer drug doxorubicin.http://link.springer.com/article/10.1186/s13065-019-0559-xAminoacetophenoneIsobenzofuran-13-dioneThiazoleHydrazonoyl halideThiazolo[4 |
| spellingShingle | Mona A. Hosny Yasser H. Zaki Wafaa A. Mokbel Abdou O. Abdelhamid Synthesis of novel thiazole, pyranothiazole, thiazolo[4,5-b]pyridines and thiazolo[5′,4′:5,6]pyrano[2,3-d]pyrimidine derivatives and incorporating isoindoline-1,3-dione group BMC Chemistry Aminoacetophenone Isobenzofuran-1 3-dione Thiazole Hydrazonoyl halide Thiazolo[4 |
| title | Synthesis of novel thiazole, pyranothiazole, thiazolo[4,5-b]pyridines and thiazolo[5′,4′:5,6]pyrano[2,3-d]pyrimidine derivatives and incorporating isoindoline-1,3-dione group |
| title_full | Synthesis of novel thiazole, pyranothiazole, thiazolo[4,5-b]pyridines and thiazolo[5′,4′:5,6]pyrano[2,3-d]pyrimidine derivatives and incorporating isoindoline-1,3-dione group |
| title_fullStr | Synthesis of novel thiazole, pyranothiazole, thiazolo[4,5-b]pyridines and thiazolo[5′,4′:5,6]pyrano[2,3-d]pyrimidine derivatives and incorporating isoindoline-1,3-dione group |
| title_full_unstemmed | Synthesis of novel thiazole, pyranothiazole, thiazolo[4,5-b]pyridines and thiazolo[5′,4′:5,6]pyrano[2,3-d]pyrimidine derivatives and incorporating isoindoline-1,3-dione group |
| title_short | Synthesis of novel thiazole, pyranothiazole, thiazolo[4,5-b]pyridines and thiazolo[5′,4′:5,6]pyrano[2,3-d]pyrimidine derivatives and incorporating isoindoline-1,3-dione group |
| title_sort | synthesis of novel thiazole pyranothiazole thiazolo 4 5 b pyridines and thiazolo 5 4 5 6 pyrano 2 3 d pyrimidine derivatives and incorporating isoindoline 1 3 dione group |
| topic | Aminoacetophenone Isobenzofuran-1 3-dione Thiazole Hydrazonoyl halide Thiazolo[4 |
| url | http://link.springer.com/article/10.1186/s13065-019-0559-x |
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