| Journal: | Anais da Academia Brasileira de Ciencias |
| Database: | PERIÓDICA |
| System number: | 000419764 |
| ISSN: | 0001-3765 |
| Authors: | Chipoline, Ingrid C1 Albes, Evelyne2 Branco, Paola2 Costa-Lotufo, Leticia V2 Ferreira, Vitor F3 Silva, Fernando C. da1 |
| Institutions: | 1Universidade Federal Fluminense, Instituto de Quimica Organica, Niteroi, Rio de Janeiro. Brasil 2Universidade de Sao Paulo, Departamento de Farmacologia, Sao Paulo. Brasil 3Universidade Federal Fluminense, Faculdade de Farmacia, Niteroi, Rio de Janeiro. Brasil |
| Year: | 2018 |
| Season: | May |
| Volumen: | 90 |
| Number: | 1 |
| Pages: | 1027-1034 |
| Country: | Brasil |
| Language: | Inglés |
| Document type: | Artículo |
| Approach: | Experimental, aplicado |
| English abstract | The 1,2-naphthoquinone compound was previously considered active against solid tumors. Moreover, glycosidase inhibitors such as 1,2,3-1H triazoles has been pointed out as efficient compounds in anticancer activity studies. Thus, a series of eleven 1,2-naphthoquinones tethered in C2 to 1,2,3-1H-triazoles 9a-k were designed, synthesized and their cytotoxic activity evaluated using HCT-116 (colon adenocarcinoma), MCF-7 (breast adenocarcinoma) and RPE (human nontumor cell line from retinal epithelium). The chemical synthesis was performed from C-3 allylation of lawsone followed by iodocyclization with subsequent nucleophilic displacement with sodium azide and, finally, the 1,3-dipolar cycloaddition catalyzed by Cu(I) with terminal alkynes led to the formation of 1H-1,2,3-Triazol-1-ylmethyl-2,3-dihydronaphtho[1,2-b]furan-4,5-diones in good yields. Compounds containing aromatic group linked to 1,2,3-triazole ring (9c, 9d, 9e, 9i) presented superior cytotoxic activity against cancer cell lines with IC50 in the range of 0.74 to 4.4 µM indicating that the presence of aromatic rings substituents in the 1,2,3-1H-triazole moiety is probably responsible for the improved cytotoxic activity |
| Disciplines: | Medicina, Química |
| Keyword: | Química farmacéutica, Oncología, Antitumorales, Naftoquinonas, 1,2,3-triazoles, Actividad citotóxica, Adenocarcinoma, Colon, Mama |
| Keyword: | Medicinal chemistry, Oncology, Antitumoral agents, Naphtoquinones, 1,2,3-triazoles, Cytotoxic activity, Adenocarcinoma, Colon, Breast |
| Full text: | Texto completo (Ver HTML) |
