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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todo:paper_02235234_v47_n1_p104_Avanzo2023-10-03T15:11:14Z 1,2,4-Triazole d-ribose derivatives: Design, synthesis and antitumoral evaluation Avanzo, R.E. Anesini, C. Fascio, M.L. Errea, M.I. D'Accorso, N.B. 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 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. Fil:Fascio, M.L. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Errea, M.I. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:D'Accorso, N.B. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_02235234_v47_n1_p104_Avanzo |
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Universidad de Buenos Aires |
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I-28 |
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R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
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 |
| spellingShingle |
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 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 |
| topic_facet |
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 |
| description |
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. |
| format |
JOUR |
| author |
Avanzo, R.E. Anesini, C. Fascio, M.L. Errea, M.I. D'Accorso, N.B. |
| author_facet |
Avanzo, R.E. Anesini, C. Fascio, M.L. Errea, M.I. D'Accorso, N.B. |
| author_sort |
Avanzo, R.E. |
| title |
1,2,4-Triazole d-ribose derivatives: Design, synthesis and antitumoral evaluation |
| title_short |
1,2,4-Triazole d-ribose derivatives: Design, synthesis and antitumoral evaluation |
| title_full |
1,2,4-Triazole d-ribose derivatives: Design, synthesis and antitumoral evaluation |
| title_fullStr |
1,2,4-Triazole d-ribose derivatives: Design, synthesis and antitumoral evaluation |
| title_full_unstemmed |
1,2,4-Triazole d-ribose derivatives: Design, synthesis and antitumoral evaluation |
| title_sort |
1,2,4-triazole d-ribose derivatives: design, synthesis and antitumoral evaluation |
| url |
http://hdl.handle.net/20.500.12110/paper_02235234_v47_n1_p104_Avanzo |
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