Design, Synthesis, and Biological Evaluations of Novel Azothiazoles Based on Thioamide
Herein we studied the preparation of different thiazoles via the reaction of 2-(3,4-dimethoxybenzylidene)hydrazine-1-carbothioamide (<b>1</b>) with hydrazonoyl halides under base-catalyzed conditions. The reactions proceed through nucleophilic substitution attack at the halogen atom of t...
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| Format: | Article |
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MDPI AG
2022-07-01
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| Series: | Current Issues in Molecular Biology |
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| Online Access: | https://www.mdpi.com/1467-3045/44/7/204 |
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| author | Abdelwahed R. Sayed Hany Elsawy Saad Shaaban Sobhi M. Gomha Yasair S. Al-Faiyz |
| author_facet | Abdelwahed R. Sayed Hany Elsawy Saad Shaaban Sobhi M. Gomha Yasair S. Al-Faiyz |
| author_sort | Abdelwahed R. Sayed |
| collection | DOAJ |
| description | Herein we studied the preparation of different thiazoles via the reaction of 2-(3,4-dimethoxybenzylidene)hydrazine-1-carbothioamide (<b>1</b>) with hydrazonoyl halides under base-catalyzed conditions. The reactions proceed through nucleophilic substitution attack at the halogen atom of the hydrazonoyl halides by the thiol nucleophile to form an <i>S</i>-alkylated intermediate. The latter intermediate undergoes cyclization by the loss of water to afford the final products. The structures of the azo compounds were confirmed by FTIR, MS, NMR, and elemental analyses. Indeed, the newly synthesized azo compounds were estimated for their potential anticancer activities by an MTT assay against different human cancer cells, such as lung adenocarcinoma (A549) and colorectal adenocarcinoma (DLD-1). The caspase-3 levels were also estimated using Western blotting and the dual staining technique to evaluate the potency of the titled compounds to promote apoptosis. |
| first_indexed | 2024-03-09T04:53:41Z |
| format | Article |
| id | doaj.art-16dd12617c19452ea15c24644cbc07d7 |
| institution | Directory Open Access Journal |
| issn | 1467-3037 1467-3045 |
| language | English |
| last_indexed | 2024-03-09T04:53:41Z |
| publishDate | 2022-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Current Issues in Molecular Biology |
| spelling | doaj.art-16dd12617c19452ea15c24644cbc07d72023-12-03T13:07:58ZengMDPI AGCurrent Issues in Molecular Biology1467-30371467-30452022-07-014472956296610.3390/cimb44070204Design, Synthesis, and Biological Evaluations of Novel Azothiazoles Based on ThioamideAbdelwahed R. Sayed0Hany Elsawy1Saad Shaaban2Sobhi M. Gomha3Yasair S. Al-Faiyz4Department of Chemistry, Faculty of Science, King Faisal University, P.O. Box 380, Hofuf 31982, Saudi ArabiaDepartment of Chemistry, Faculty of Science, King Faisal University, P.O. Box 380, Hofuf 31982, Saudi ArabiaDepartment of Chemistry, Faculty of Science, King Faisal University, P.O. Box 380, Hofuf 31982, Saudi ArabiaDepartment of Chemistry, Faculty of Science, Cairo University, Giza 12613, EgyptDepartment of Chemistry, Faculty of Science, King Faisal University, P.O. Box 380, Hofuf 31982, Saudi ArabiaHerein we studied the preparation of different thiazoles via the reaction of 2-(3,4-dimethoxybenzylidene)hydrazine-1-carbothioamide (<b>1</b>) with hydrazonoyl halides under base-catalyzed conditions. The reactions proceed through nucleophilic substitution attack at the halogen atom of the hydrazonoyl halides by the thiol nucleophile to form an <i>S</i>-alkylated intermediate. The latter intermediate undergoes cyclization by the loss of water to afford the final products. The structures of the azo compounds were confirmed by FTIR, MS, NMR, and elemental analyses. Indeed, the newly synthesized azo compounds were estimated for their potential anticancer activities by an MTT assay against different human cancer cells, such as lung adenocarcinoma (A549) and colorectal adenocarcinoma (DLD-1). The caspase-3 levels were also estimated using Western blotting and the dual staining technique to evaluate the potency of the titled compounds to promote apoptosis.https://www.mdpi.com/1467-3045/44/7/204thiazolehydrazonoylcarbothioamideanticancer activities |
| spellingShingle | Abdelwahed R. Sayed Hany Elsawy Saad Shaaban Sobhi M. Gomha Yasair S. Al-Faiyz Design, Synthesis, and Biological Evaluations of Novel Azothiazoles Based on Thioamide Current Issues in Molecular Biology thiazole hydrazonoyl carbothioamide anticancer activities |
| title | Design, Synthesis, and Biological Evaluations of Novel Azothiazoles Based on Thioamide |
| title_full | Design, Synthesis, and Biological Evaluations of Novel Azothiazoles Based on Thioamide |
| title_fullStr | Design, Synthesis, and Biological Evaluations of Novel Azothiazoles Based on Thioamide |
| title_full_unstemmed | Design, Synthesis, and Biological Evaluations of Novel Azothiazoles Based on Thioamide |
| title_short | Design, Synthesis, and Biological Evaluations of Novel Azothiazoles Based on Thioamide |
| title_sort | design synthesis and biological evaluations of novel azothiazoles based on thioamide |
| topic | thiazole hydrazonoyl carbothioamide anticancer activities |
| url | https://www.mdpi.com/1467-3045/44/7/204 |
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