Artículo
Avanzo, R.E.; Padrón, J.M.; D'Accorso, N.B.; Fascio, M.L. "Synthesis and in vitro antiproliferative activities of (5-aryl-1,2,4-oxadiazole-3-yl) methyl D-ribofuranosides" (2017) Bioorganic and Medicinal Chemistry Letters. 27(16):3674-3677
Estamos trabajando para incorporar este artículo al repositorio
Consulte la política de Acceso Abierto del editor
Abstract:
The emergence of multidrug resistance cell lines is one of the major obstacles in the success of cancer chemotherapeutic treatment. Therefore, it remains a big challenge the development of new and effective drugs to defeat cancer. The presence of nitrogen heterocycles in the architectural design of drugs has led to the discovery of new leading compounds. Herein, we report the synthesis, characterization and in vitro antiproliferative activity against six cancer cell lines of D-ribofuranoside derivatives bearing a 1,2,4-oxadiazolic ring, with the aim of developing new active compounds. Most of these derivatives exhibit significant antiproliferative activities in the micromolar range. Noteworthy, the most potent compound of the series showed better selectivity towards the more resistant colon cancer cell line WiDr. © 2017 Elsevier Ltd
Registro:
| Documento: | Artículo |
| Título: | Synthesis and in vitro antiproliferative activities of (5-aryl-1,2,4-oxadiazole-3-yl) methyl D-ribofuranosides |
| Autor: | Avanzo, R.E.; Padrón, J.M.; D'Accorso, N.B.; Fascio, M.L. |
| Filiación: | Universidad de Buenos Aires, Facultad de Ciencias Exactas y Naturales, Departamento de Química Orgánica, Buenos Aires, Argentina BioLab, Instituto Universitario de Bio-Orgánica “Antonio González” (IUBO-AG), Centro de Investigaciones Biomédicas de Canarias (CIBICAN), Universidad de La Laguna, La Laguna, 38206, Spain CONICET – Universidad de Buenos Aires, Centro de Investigaciones en Hidratos de Carbono (CIHIDECAR), Buenos Aires, Argentina |
| Palabras clave: | 1,2,4-Oxadiazole; 1,2,4-Triazole; 5-Amino-1,3,4-thiadiazole; Antiproliferative activity; D-Ribose; (5 aryl oxadiazole 3 yl) methyl dextro ribofuranoside derivative; antineoplastic agent; unclassified drug; antineoplastic agent; oxadiazole derivative; ribose; A-549 cell line; antineoplastic activity; antiproliferative activity; apoptosis; Article; cell proliferation; colon cancer cell line; controlled study; drug synthesis; G1 phase cell cycle checkpoint; HeLa cell line; human; human cell; in vitro study; lymphoma cell line; prostate cancer cell line; renal cancer cell line; structure activity relation; analogs and derivatives; chemistry; drug effects; drug screening; synthesis; tumor cell line; Antineoplastic Agents; Cell Line, Tumor; Cell Proliferation; Drug Screening Assays, Antitumor; Humans; Oxadiazoles; Ribose; Structure-Activity Relationship |
| Año: | 2017 |
| Volumen: | 27 |
| Número: | 16 |
| Página de inicio: | 3674 |
| Página de fin: | 3677 |
| DOI: | http://dx.doi.org/10.1016/j.bmcl.2017.07.015 |
| Título revista: | Bioorganic and Medicinal Chemistry Letters |
| Título revista abreviado: | Bioorg. Med. Chem. Lett. |
| ISSN: | 0960894X |
| CODEN: | BMCLE |
| CAS: | ribose, 34466-20-1, 50-69-1, 93781-19-2; Antineoplastic Agents; Oxadiazoles; Ribose |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0960894X_v27_n16_p3674_Avanzo |
Referencias:
- Vander Heiden, M.G., Cantley, L.C., Thompson, C.B., (2009) Science, 324, p. 1029
- Flaveny, C.A., Griffett, K., El-Gendy, B.E.-D.M., (2015) Cancer Cell, 28, p. 1
- Jordheim, L.P., Durantel, D., Zoulim, F., Dumontet, C., (2013) Nat Rev Drug Disc, 12, p. 447
- Moeker, J., Mahon, B.P., Bornaghi, L.F., (2014) J Med Chem, 57, p. 8635
- Avanzo, R.E., Anesini, C., Fascio, M.L., Errea, M.I., D'Accorso, N.B., (2012) Eur J Med Chem, 47, p. 104
- Gueron, G., Avanzo, R.E., Schuster, F., Carabelos, M.N., Vazquez, E., Fascio, M.L., D'Accorso, N.B., (2014) Biomed Pharmacother, 68, p. 847
- Akhtar, J., Khan, A.A., Ali, Z., Haider, R., Yar, M.S., (2017) Eur J Med Chem, 125, p. 143
- McBriar, M.D., Clader, J.W., Chu, I., (2008) Bioorg Med Chem Lett, 18, p. 215
- Gilmore, J.L., Sheppeck, J.E., Watterson, S.H., (2016) J Med Chem, 59, p. 6248
- Rosenberg, A.J., Liu, H., Jin, H., Yue, X., Riley, S., Brown, S.J., Tu, Z., (2016) J Med Chem, 59, p. 6201
- Maftei, C.V., Fodor, E., Jones, P.G., (2016) Tetrahedron, 72, p. 1185
- Han, M., Li, S., Ai, J., (2016) Bioorg Med Chem Lett, 26, p. 5679
- Jain, A.K., Sharma, S., Vaidya, A., Ravichandran, V., Agrawal, R.K., (2013) Chem Biol Drug Des, 81, p. 557
- Shi, W., Hu, J., Bao, N., Li, D., Chen, L., Sun, J., (2017) Bioorg Med Chem Lett, 27, p. 147
- Nieto, D., Bruña, S., González-Vadillo, A.M., (2015) Organometallics, 34, p. 5407
Citas:
---------- APA ----------
Avanzo, R.E., Padrón, J.M., D'Accorso, N.B. & Fascio, M.L. (2017) . Synthesis and in vitro antiproliferative activities of (5-aryl-1,2,4-oxadiazole-3-yl) methyl D-ribofuranosides. Bioorganic and Medicinal Chemistry Letters, 27(16), 3674-3677.http://dx.doi.org/10.1016/j.bmcl.2017.07.015
---------- CHICAGO ----------
Avanzo, R.E., Padrón, J.M., D'Accorso, N.B., Fascio, M.L. "Synthesis and in vitro antiproliferative activities of (5-aryl-1,2,4-oxadiazole-3-yl) methyl D-ribofuranosides" . Bioorganic and Medicinal Chemistry Letters 27, no. 16 (2017) : 3674-3677.http://dx.doi.org/10.1016/j.bmcl.2017.07.015
---------- MLA ----------
Avanzo, R.E., Padrón, J.M., D'Accorso, N.B., Fascio, M.L. "Synthesis and in vitro antiproliferative activities of (5-aryl-1,2,4-oxadiazole-3-yl) methyl D-ribofuranosides" . Bioorganic and Medicinal Chemistry Letters, vol. 27, no. 16, 2017, pp. 3674-3677.http://dx.doi.org/10.1016/j.bmcl.2017.07.015
---------- VANCOUVER ----------
Avanzo, R.E., Padrón, J.M., D'Accorso, N.B., Fascio, M.L. Synthesis and in vitro antiproliferative activities of (5-aryl-1,2,4-oxadiazole-3-yl) methyl D-ribofuranosides. Bioorg. Med. Chem. Lett. 2017;27(16):3674-3677.http://dx.doi.org/10.1016/j.bmcl.2017.07.015
