Synthesis and cytotoxicity evaluation of thiazole conjugated amino acid derivatives
This paper presents the three-step synthesis and cytotoxicity evaluation of the thiazole-conjugated amino acid derivatives. Starting from the commercially available benzophenone and thiourea, the thiazole structure was successfully constructed bearing the free amino groups at the C-2 position, whic...
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| Main Authors: | , , , , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Can Tho University Publisher
2025-06-01
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| Series: | CTU Journal of Innovation and Sustainable Development |
| Subjects: | |
| Online Access: | https://ctujs.ctu.edu.vn/index.php/ctujs/article/view/1054 |
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| Summary: | This paper presents the three-step synthesis and cytotoxicity evaluation of the thiazole-conjugated amino acid derivatives. Starting from the commercially available benzophenone and thiourea, the thiazole structure was successfully constructed bearing the free amino groups at the C-2 position, which was then coupled with the carboxyl functionality of N-Boc L-phenylalanine, N-Boc L-proline and N-Boc L-tryptophane using CDI as the coupling reagent under mild basic conditions to provide the hybrid thiazole/N-Boc amino acid derivatives 5a-c. Finally, the acidic promoted deprotection of the Boc groups afforded the desired hybrid thiazole/amino acid derivatives 6a-c in reasonable total yields. Cytotoxicity assays indicated that the hybrids thiazole/L-proline (6a) and thiazole/L-tryptophan (6c) exhibited rather good cytotoxicity on the cervical cancer cell line (IC50 =18.86 and 18.25 µM, respectively). Notably, compound 5a having the thiazole conjugated with unprotected N-Boc L-phenylalanine showed very good activity towards the lung cancer (IC50 = 15.72 µM), the cervical cancer (IC50 = 8.98 µM) and the breast cancer cell lines (IC50 = 8.07 µM), which were 1.3-, 1.2- and 2.5-fold, respectively, stronger activity than 5-FU (IC50 = 20.73, 10.67 and 20.43 µM, respectively).
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| ISSN: | 2588-1418 2815-6412 |