Artículo
Avanzo, R.E.; Anesini, C.; Fascio, M.L.; Errea, M.I.; D'Accorso, N.B. "1,2,4-Triazole d-ribose derivatives: Design, synthesis and antitumoral evaluation" (2012) European Journal of Medicinal Chemistry. 47(1):104-110
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Abstract:
Herein we report the design, synthesis and characterization of novel 1,2,4-triazole d-ribose derivatives, as well as their synthetic precursors. The antitumoral activity against T cell lymphoma cell line of these products was studied. Structures containing a 1,2,4-triazolic ring linked by sulfur to the carbohydrate moiety showed a moderate antiproliferative activity. The presence of the second heterocyclic ring did not show significant changes in their biological activity. Meanwhile, structures with 3-thiobenzyl-5-substituted-1,2, 4-triazole ring linked by nitrogen leads to compounds with a biphasic behavior, stimulating cell proliferation at low concentrations and inhibiting it at higher ones. An increment in the polarity was associated with a decrease in the activity of the evaluated compounds. A preliminary antitumoral screening pointed the 1,2,4-triazolic structures linked to protected sugars as promising leaders for further studies. © 2011 Elsevier Masson SAS. All rights reserved.
Registro:
| Documento: | Artículo |
| Título: | 1,2,4-Triazole d-ribose derivatives: Design, synthesis and antitumoral evaluation |
| Autor: | Avanzo, R.E.; Anesini, C.; Fascio, M.L.; Errea, M.I.; D'Accorso, N.B. |
| Filiación: | CIHIDECAR-CONICET, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, 1428 Buenos Aires, Argentina Instituto de Química y Metabolismo Del Fármaco (IQUIMEFA-UBA-CONICET), Facultad de Farmacia y Bioquímica, UBA, Junín 956 2do piso, Ciudad Autónoma de Buenos Aires, Argentina Instituto Tecnológico de Buenos Aires, Madero 399, Ciudad de Buenos Aires, Argentina |
| Palabras clave: | 1,2,4-Triazole; Antitumoral activity; d-ribose; Isoxazoline; 1,2,4 triazole dextro ribose derivative; [3 (3,4,5 trimethoxyphenyl) isoxazolin 5 yl]methyl 5 deoxy 5 (1,2,4 triazol 3 yl) 2,3 o cyclopentylidene beta dextro ribofuranoside; [3 (3,4,5 trimethoxyphenyl) isoxazolin 5 yl]methyl 5 deoxy 5 (1,2,4 triazol 3 yl)beta dextro ribofuranoside; [3 (3,4,5 trimethoxyphenyl) isoxazolin 5 yl]methyl 5 deoxy 5 [(5 4 chlorophenyl 3 thiobenzyl) 1,2,4 triazol 4 yl] 2,3 o cyclopentylidene beta dextro ribofuranoside; [3 (3,4,5 trimethoxyphenyl) isoxazolin 5 yl]methyl 5 deoxy 5 [(5 4 chlorophenyl 3 thiobenzyl) 1,2,4 triazol 4 yl]beta dextro ribofuranoside; allyl 2,3 o cyclopentylidene 5 deoxy 5 (1,2,4 triazol 3 yl)beta dextro ribofuranoside; allyl 5 deoxy 5 (1,2,4 triazol 3 yl)beta dextro ribofuranoside; allyl 5 deoxy 5 [(5 4 chlorophenyl 3 thiobenzyl) 1,2,4 triazol 4 yl] 2,3 o cyclopentylidene beta dextro ribofuranoside; allyl 5 deoxy 5 [(5 4 chlorophenyl 3 thionyl) 1,2,4 triazolin 4 yl]beta dextro ribofuranoside; antineoplastic agent; isoxazoline derivative; nitrogen; ribose; sulfur; triazole derivative; unclassified drug; antineoplastic activity; antiproliferative activity; article; cancer cell culture; carbohydrate analysis; cell polarity; cell proliferation; drug activity; drug design; drug structure; drug synthesis; human; human cell; metastasis; pharmacophore; T cell lymphoma; Antineoplastic Agents; Cell Line, Tumor; Cell Proliferation; Drug Design; Humans; Neoplasm Invasiveness; Neoplasm Metastasis; Ribose; Triazoles |
| Año: | 2012 |
| Volumen: | 47 |
| Número: | 1 |
| Página de inicio: | 104 |
| Página de fin: | 110 |
| DOI: | http://dx.doi.org/10.1016/j.ejmech.2011.10.028 |
| Título revista: | European Journal of Medicinal Chemistry |
| Título revista abreviado: | Eur. J. Med. Chem. |
| ISSN: | 02235234 |
| CODEN: | EJMCA |
| CAS: | nitrogen, 7727-37-9; ribose, 34466-20-1, 50-69-1, 93781-19-2; sulfur, 13981-57-2, 7704-34-9; 1,2,4-triazole, 288-88-0; Antineoplastic Agents; Ribose, 50-69-1; Triazoles |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_02235234_v47_n1_p104_Avanzo |
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Citas:
---------- APA ----------
Avanzo, R.E., Anesini, C., Fascio, M.L., Errea, M.I. & D'Accorso, N.B. (2012) . 1,2,4-Triazole d-ribose derivatives: Design, synthesis and antitumoral evaluation. European Journal of Medicinal Chemistry, 47(1), 104-110.http://dx.doi.org/10.1016/j.ejmech.2011.10.028
---------- CHICAGO ----------
Avanzo, R.E., Anesini, C., Fascio, M.L., Errea, M.I., D'Accorso, N.B. "1,2,4-Triazole d-ribose derivatives: Design, synthesis and antitumoral evaluation" . European Journal of Medicinal Chemistry 47, no. 1 (2012) : 104-110.http://dx.doi.org/10.1016/j.ejmech.2011.10.028
---------- MLA ----------
Avanzo, R.E., Anesini, C., Fascio, M.L., Errea, M.I., D'Accorso, N.B. "1,2,4-Triazole d-ribose derivatives: Design, synthesis and antitumoral evaluation" . European Journal of Medicinal Chemistry, vol. 47, no. 1, 2012, pp. 104-110.http://dx.doi.org/10.1016/j.ejmech.2011.10.028
---------- VANCOUVER ----------
Avanzo, R.E., Anesini, C., Fascio, M.L., Errea, M.I., D'Accorso, N.B. 1,2,4-Triazole d-ribose derivatives: Design, synthesis and antitumoral evaluation. Eur. J. Med. Chem. 2012;47(1):104-110.http://dx.doi.org/10.1016/j.ejmech.2011.10.028
