1,2,4-Triazole d-ribose derivatives: Design, synthesis and antitumoral evaluation
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...
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| Otros Autores: | , , , |
| Formato: | Capítulo de libro |
| Lenguaje: | Inglés |
| Publicado: |
2012
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
| Aporte de: | Registro referencial: Solicitar el recurso aquí |
| LEADER | 09619caa a22011537a 4500 | ||
|---|---|---|---|
| 001 | PAPER-9938 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203955.0 | ||
| 008 | 190411s2012 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-84855776626 | |
| 024 | 7 | |2 cas |a 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 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a EJMCA | ||
| 100 | 1 | |a Avanzo, R.E. | |
| 245 | 1 | 0 | |a 1,2,4-Triazole d-ribose derivatives: Design, synthesis and antitumoral evaluation |
| 260 | |c 2012 | ||
| 270 | 1 | 0 | |m D'Accorso, N.B.; CIHIDECAR-CONICET, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, 1428 Buenos Aires, Argentina; email: norma@qo.fcen.uba.ar |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Kumar, D., Kumar Narayanam, M., Chang, K.-H., Shah, K., Synthesis of novel indolyl-1,2,4-triazoles as potent and selective anticancer agents (2011) Chem. Biol. Drug Des., 77, pp. 182-188 | ||
| 504 | |a Holla, B.S., Veerendra, B., Shivananda, M.K., Poojary, B., Synthesis characterization and anticancer activity studies on some Mannich bases derived from 1,2,4-triazoles (2003) Eur. J. Med. Chem., 38, pp. 759-767 | ||
| 504 | |a Bekircan, O., Bektas, H., Synthesis of new bis-1,2,4-triazole derivatives (2006) Molecules, 11, pp. 469-477 | ||
| 504 | |a Liu, Y., Xia, Y., Fan, Y., Maggiani, A., Rocchi, P., Qu, F., Iovanna, J.L., Peng, L., N-aryltriazole ribonucleosides with potent antiproliferative activity against drug-resistant pancreatic cancer (2010) Bioorg. Med. Chem. Lett., 20, pp. 2503-2507 | ||
| 504 | |a Wan, J., Xia, Y., Liu, Y., Wang, M., Rocchi, P., Yao, J., Qu, F., Peng, L., Discovery of novel arylethynyltriazole ribonucleosides with selective and effective antiviral and antiproliferative activity (2009) J. Med. Chem., 52, pp. 1144-1155 | ||
| 504 | |a Whiting, M., Muldoon, J., Lin, Y.C., Silverman, S.M., Lindstrom, W., Olson, A.J., Kolb, H.C., Fokin, V.V., Inhibitors of HIV-1 protease by using in situ click chemistry (2006) Angew. Chem. Int. Ed., 45, pp. 1435-1439 | ||
| 504 | |a Lee, Y.-S., Park, S.M., Kim, H.M., Park, S.-K., Lee, K., Lee, C.W., Kim, B.H., C5-Modified nucleosides exhibiting anticancer activity (2009) Bioorg. Med. Chem. Lett., 19, pp. 4688-4691 | ||
| 504 | |a Kamal, A., Vijaya Bharathi, E., Surendranadha Reddy, J., Janaki Ramaiah, M., Dastagiri, D., Kashi Reddy, M., Viswanath, A., Bhadra, M.P., Synthesis and biological evaluation of 3,5-diaryl isoxazoline/isoxazole linked 2,3-dihydroquinazolinone hybrids as anticancer agents (2011) Eur. J. Med. Chem., 46, pp. 691-703 | ||
| 504 | |a Soural, M., Bouillon, I., Krchňák, V., Combinatorial libraries of bis-heterocyclic compounds with skeletal diversity (2008) J. Comb. Chem., 10, pp. 923-933 | ||
| 504 | |a Liu, Z., Yang, G., Qin, X., Syntheses and biological activities of novel diheterocyclic compounds containing 1,2,4-triazolo[1,5-a]pyrimidine and 1,3,4-oxadiazole (2001) J. Chem. Technol. Biotechnol., 76, pp. 1154-1158 | ||
| 504 | |a Edwards, P.J., The design and synthesis of libraries for the discovery of antibacterial and antifungal substances (2011) Drug Discov. Today, 16, pp. 278-279 | ||
| 504 | |a Verschueren, H., Van Der Taelen, I., Dewit, J., De Braekeleer, J., De Baetselier, P., Metastatic competence of BW5147 T-lymphoma cell lines is correlated with in vitro invasiveness, motility and F-actin content (1994) J. Leukoc. Biol., 55, pp. 552-556 | ||
| 504 | |a Busscher, G.F., Van Den Broek, S.A.M.W., Rutjes, F.P.J.T., Van Delft, F.L., Carbohydrate mimic of 2-deoxystreptamine for the preparation of conformationally constrained aminoglycosides (2007) Tetrahedron, 63, pp. 3183-3188 | ||
| 504 | |a Barradas, J.S., Errea, M.I., D'Accorso, N.B., Sepúlveda, C.S., Talarico, L.B., Damonte, E.B., Synthesis and antiviral activity of azoles obtained from carbohydrates (2008) Carbohydr. Res., 343, pp. 2468-2474 | ||
| 504 | |a Anesini, C., Genaro, A., Cremaschi, G., Sterin Borda, L., Cazux, C., Borda, E., Immunomodulatory activity of Larrea divaricata Cav. (1996) Fitoterapia, 67, pp. 329-333 | ||
| 504 | |a Cremaschi, G., Fisher, P., Boege, F., ß adrenoceptor distribution in murine lymphoid cell line (1991) Immunopharmacology, 22, pp. 195-206 | ||
| 520 | 3 | |a 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. |l eng | |
| 536 | |a Detalles de la financiación: Agencia Nacional de Promoción Científica y Tecnológica | ||
| 536 | |a Detalles de la financiación: Universidad de Buenos Aires | ||
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas | ||
| 536 | |a Detalles de la financiación: Research was supported by Agencia Nacional de Promoción Científica y Tecnológica , Consejo Nacional de Investigaciones Científicas y Técnicas (CONICET) and Universidad de Buenos Aires (UBA) , Argentina. C.A. and N.B.D. are members of Research Career from CONICET. | ||
| 593 | |a CIHIDECAR-CONICET, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, 1428 Buenos Aires, Argentina | ||
| 593 | |a 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 | ||
| 593 | |a Instituto Tecnológico de Buenos Aires, Madero 399, Ciudad de Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a 1,2,4-TRIAZOLE |
| 690 | 1 | 0 | |a ANTITUMORAL ACTIVITY |
| 690 | 1 | 0 | |a D-RIBOSE |
| 690 | 1 | 0 | |a ISOXAZOLINE |
| 690 | 1 | 0 | |a 1,2,4 TRIAZOLE DEXTRO RIBOSE DERIVATIVE |
| 690 | 1 | 0 | |a [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 |
| 690 | 1 | 0 | |a [3 (3,4,5 TRIMETHOXYPHENYL) ISOXAZOLIN 5 YL]METHYL 5 DEOXY 5 (1,2,4 TRIAZOL 3 YL)BETA DEXTRO RIBOFURANOSIDE |
| 690 | 1 | 0 | |a [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 |
| 690 | 1 | 0 | |a [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 |
| 690 | 1 | 0 | |a ALLYL 2,3 O CYCLOPENTYLIDENE 5 DEOXY 5 (1,2,4 TRIAZOL 3 YL)BETA DEXTRO RIBOFURANOSIDE |
| 690 | 1 | 0 | |a ALLYL 5 DEOXY 5 (1,2,4 TRIAZOL 3 YL)BETA DEXTRO RIBOFURANOSIDE |
| 690 | 1 | 0 | |a ALLYL 5 DEOXY 5 [(5 4 CHLOROPHENYL 3 THIOBENZYL) 1,2,4 TRIAZOL 4 YL] 2,3 O CYCLOPENTYLIDENE BETA DEXTRO RIBOFURANOSIDE |
| 690 | 1 | 0 | |a ALLYL 5 DEOXY 5 [(5 4 CHLOROPHENYL 3 THIONYL) 1,2,4 TRIAZOLIN 4 YL]BETA DEXTRO RIBOFURANOSIDE |
| 690 | 1 | 0 | |a ANTINEOPLASTIC AGENT |
| 690 | 1 | 0 | |a ISOXAZOLINE DERIVATIVE |
| 690 | 1 | 0 | |a NITROGEN |
| 690 | 1 | 0 | |a RIBOSE |
| 690 | 1 | 0 | |a SULFUR |
| 690 | 1 | 0 | |a TRIAZOLE DERIVATIVE |
| 690 | 1 | 0 | |a UNCLASSIFIED DRUG |
| 690 | 1 | 0 | |a ANTINEOPLASTIC ACTIVITY |
| 690 | 1 | 0 | |a ANTIPROLIFERATIVE ACTIVITY |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CANCER CELL CULTURE |
| 690 | 1 | 0 | |a CARBOHYDRATE ANALYSIS |
| 690 | 1 | 0 | |a CELL POLARITY |
| 690 | 1 | 0 | |a CELL PROLIFERATION |
| 690 | 1 | 0 | |a DRUG ACTIVITY |
| 690 | 1 | 0 | |a DRUG DESIGN |
| 690 | 1 | 0 | |a DRUG STRUCTURE |
| 690 | 1 | 0 | |a DRUG SYNTHESIS |
| 690 | 1 | 0 | |a HUMAN |
| 690 | 1 | 0 | |a HUMAN CELL |
| 690 | 1 | 0 | |a METASTASIS |
| 690 | 1 | 0 | |a PHARMACOPHORE |
| 690 | 1 | 0 | |a T CELL LYMPHOMA |
| 690 | 1 | 0 | |a ANTINEOPLASTIC AGENTS |
| 690 | 1 | 0 | |a CELL LINE, TUMOR |
| 690 | 1 | 0 | |a CELL PROLIFERATION |
| 690 | 1 | 0 | |a DRUG DESIGN |
| 690 | 1 | 0 | |a HUMANS |
| 690 | 1 | 0 | |a NEOPLASM INVASIVENESS |
| 690 | 1 | 0 | |a NEOPLASM METASTASIS |
| 690 | 1 | 0 | |a RIBOSE |
| 690 | 1 | 0 | |a TRIAZOLES |
| 700 | 1 | |a Anesini, C. | |
| 700 | 1 | |a Fascio, M.L. | |
| 700 | 1 | |a Errea, M.I. | |
| 700 | 1 | |a D'Accorso, N.B. | |
| 773 | 0 | |d 2012 |g v. 47 |h pp. 104-110 |k n. 1 |p Eur. J. Med. Chem. |x 02235234 |w (AR-BaUEN)CENRE-4668 |t European Journal of Medicinal Chemistry | |
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