Synthesis and antiviral activity of azoles obtained from carbohydrates
Herein we describe the synthesis of 1,2,4-triazolyl-3-thione;1,3,4-oxadiazole, and imidazo[2,1-b]thiazole derivatives from carbohydrates. The antiviral activity of these compounds was tested against Dengue and Junin virus (the etiological agent of Argentine hemorrhagic fever). The 3-(p-bromobenzoyl)...
Guardado en:
| Autores principales: | , , , , , |
|---|---|
| Formato: | JOUR |
| Materias: | |
| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00086215_v343_n14_p2468_Barradas |
| Aporte de: |
| id |
todo:paper_00086215_v343_n14_p2468_Barradas |
|---|---|
| record_format |
dspace |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
1,2,4-Triazolyl-3-thione 1,3,4-Oxadiazole Antiviral activity Carbohydrates Imidazo[2,1-b]thiazole Arsenic compounds Biomolecules Carbohydrates Chlorine compounds Concentration (process) Organic compounds Viruses 1,2,4-Triazolyl-3-thione 1,3,4-Oxadiazole Antiviral activities Antiviral activity Etiological agents Imidazo[2,1-b]thiazole Isopropylidene Junin virus Thiazole derivatives Vero cells Complexation 1,2 o isopropylidene alpha dextro xylopentadialdo 1,4 furanose(2 bromobenzoyl)hydrazone 1,2 o isopropylidene alpha dextro xylopentadialdo 1,4 furanose(2 chlorobenzoyl)hydrazone 1,2 o isopropylidene alpha dextro xylopentadialdo 1,4 furanose(3 bromobenzoyl)hydrazone 1,2 o isopropylidene alpha dextro xylopentadialdo 1,4 furanose(3 chlorobenzoyl)hydrazone 1,2 o isopropylidene alpha dextro xylopentadialdo 1,4 furanose(4 bromobenzoyl)hydrazone 1,2 o isopropylidene alpha dextro xylopentadialdo 1,4 furanose(4 chlorobenzoyl)hydrazone 1,2,4 triazolyl 3 thione 1,3,4 oxadiazole derivative 2 (1,2 o isopropylidene alpha dextro xylo tetrafuranos 4 yl) 5 (2 bromophenyl) 1,3,4 oxadiazole 2 (1,2 o isopropylidene alpha dextro xylo tetrafuranos 4 yl) 5 (2 chlorophenyl) 1,3,4 oxadiazole 2 (1,2 o isopropylidene alpha dextro xylo tetrafuranos 4 yl) 5 (3 bromophenyl) 1,3,4 oxadiazole 2 (1,2 o isopropylidene alpha dextro xylo tetrafuranos 4 yl) 5 (3 chlorophenyl) 1,3,4 oxadiazole 2 (1,2 o isopropylidene alpha dextro xylo tetrafuranos 4 yl) 5 (4 bromophenyl) 1,3,4 oxadiazole 2 (1,2 o isopropylidene alpha dextro xylo tetrafuranos 4 yl) 5 (4 chlorophenyl) 1,3,4 oxadiazole 3 (4 bromobenzoyl) 5 (1,2 o isopropylidene 3 o methyl alpha dextro xylofuranos 5 ulo 5 yl)imidazo[2,1 b]thiazole 3 (4 bromobenzoyl) 5 (1,2 o isopropylidene 3 o methyl alpha dextro xylofuranos 5 ulos 5 yl)imidazo[2,1 b]thiazole 3 benzoyl 5 (1,2 o isopropylidene 3 o methyl alpha dextro xylofuranos 5 ulo 5 yl)imidazo[2,1-b]thiazole 3,5 di o acetyl 6 deoxy 1,2 isopropylidene 6 [(4 bromobenzohydrazinecarbothionyl)amino]alpha dextro glucofuranose 5 (4 clorophenyl) 4 (1,2 o isopropylidene alpha dextro glucofuranos 6 yl) 1,2,4 triazoline 3 thione 6 bromo 5 deoxy 1,2 o isopropylidene 3 o methyl alpha dextro xylo hexofuranos 5 ulose 6 bromo 6 deoxy 1,2 o isopropylidene 3 o methyl alpha dextro glucofuranose antivirus agent imidazo[2,1 b]thiazole derivative n (5 benzoylthiazol 2 yl) n,n dimethylformamidine n' (5 4 bromobenzoylthiazol 2 yl) n,n dimethylformamidine unclassified drug animal cell antiviral activity article carbon nuclear magnetic resonance Dengue virus drug structure drug synthesis Junin virus nonhuman priority journal proton nuclear magnetic resonance structure activity relation Vero cell Animals Antiviral Agents Azoles Carbohydrates Cercopithecus aethiops Dengue Virus Inhibitory Concentration 50 Junin virus Toxicity Tests Vero Cells Junin virus |
| spellingShingle |
1,2,4-Triazolyl-3-thione 1,3,4-Oxadiazole Antiviral activity Carbohydrates Imidazo[2,1-b]thiazole Arsenic compounds Biomolecules Carbohydrates Chlorine compounds Concentration (process) Organic compounds Viruses 1,2,4-Triazolyl-3-thione 1,3,4-Oxadiazole Antiviral activities Antiviral activity Etiological agents Imidazo[2,1-b]thiazole Isopropylidene Junin virus Thiazole derivatives Vero cells Complexation 1,2 o isopropylidene alpha dextro xylopentadialdo 1,4 furanose(2 bromobenzoyl)hydrazone 1,2 o isopropylidene alpha dextro xylopentadialdo 1,4 furanose(2 chlorobenzoyl)hydrazone 1,2 o isopropylidene alpha dextro xylopentadialdo 1,4 furanose(3 bromobenzoyl)hydrazone 1,2 o isopropylidene alpha dextro xylopentadialdo 1,4 furanose(3 chlorobenzoyl)hydrazone 1,2 o isopropylidene alpha dextro xylopentadialdo 1,4 furanose(4 bromobenzoyl)hydrazone 1,2 o isopropylidene alpha dextro xylopentadialdo 1,4 furanose(4 chlorobenzoyl)hydrazone 1,2,4 triazolyl 3 thione 1,3,4 oxadiazole derivative 2 (1,2 o isopropylidene alpha dextro xylo tetrafuranos 4 yl) 5 (2 bromophenyl) 1,3,4 oxadiazole 2 (1,2 o isopropylidene alpha dextro xylo tetrafuranos 4 yl) 5 (2 chlorophenyl) 1,3,4 oxadiazole 2 (1,2 o isopropylidene alpha dextro xylo tetrafuranos 4 yl) 5 (3 bromophenyl) 1,3,4 oxadiazole 2 (1,2 o isopropylidene alpha dextro xylo tetrafuranos 4 yl) 5 (3 chlorophenyl) 1,3,4 oxadiazole 2 (1,2 o isopropylidene alpha dextro xylo tetrafuranos 4 yl) 5 (4 bromophenyl) 1,3,4 oxadiazole 2 (1,2 o isopropylidene alpha dextro xylo tetrafuranos 4 yl) 5 (4 chlorophenyl) 1,3,4 oxadiazole 3 (4 bromobenzoyl) 5 (1,2 o isopropylidene 3 o methyl alpha dextro xylofuranos 5 ulo 5 yl)imidazo[2,1 b]thiazole 3 (4 bromobenzoyl) 5 (1,2 o isopropylidene 3 o methyl alpha dextro xylofuranos 5 ulos 5 yl)imidazo[2,1 b]thiazole 3 benzoyl 5 (1,2 o isopropylidene 3 o methyl alpha dextro xylofuranos 5 ulo 5 yl)imidazo[2,1-b]thiazole 3,5 di o acetyl 6 deoxy 1,2 isopropylidene 6 [(4 bromobenzohydrazinecarbothionyl)amino]alpha dextro glucofuranose 5 (4 clorophenyl) 4 (1,2 o isopropylidene alpha dextro glucofuranos 6 yl) 1,2,4 triazoline 3 thione 6 bromo 5 deoxy 1,2 o isopropylidene 3 o methyl alpha dextro xylo hexofuranos 5 ulose 6 bromo 6 deoxy 1,2 o isopropylidene 3 o methyl alpha dextro glucofuranose antivirus agent imidazo[2,1 b]thiazole derivative n (5 benzoylthiazol 2 yl) n,n dimethylformamidine n' (5 4 bromobenzoylthiazol 2 yl) n,n dimethylformamidine unclassified drug animal cell antiviral activity article carbon nuclear magnetic resonance Dengue virus drug structure drug synthesis Junin virus nonhuman priority journal proton nuclear magnetic resonance structure activity relation Vero cell Animals Antiviral Agents Azoles Carbohydrates Cercopithecus aethiops Dengue Virus Inhibitory Concentration 50 Junin virus Toxicity Tests Vero Cells Junin virus 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 |
| topic_facet |
1,2,4-Triazolyl-3-thione 1,3,4-Oxadiazole Antiviral activity Carbohydrates Imidazo[2,1-b]thiazole Arsenic compounds Biomolecules Carbohydrates Chlorine compounds Concentration (process) Organic compounds Viruses 1,2,4-Triazolyl-3-thione 1,3,4-Oxadiazole Antiviral activities Antiviral activity Etiological agents Imidazo[2,1-b]thiazole Isopropylidene Junin virus Thiazole derivatives Vero cells Complexation 1,2 o isopropylidene alpha dextro xylopentadialdo 1,4 furanose(2 bromobenzoyl)hydrazone 1,2 o isopropylidene alpha dextro xylopentadialdo 1,4 furanose(2 chlorobenzoyl)hydrazone 1,2 o isopropylidene alpha dextro xylopentadialdo 1,4 furanose(3 bromobenzoyl)hydrazone 1,2 o isopropylidene alpha dextro xylopentadialdo 1,4 furanose(3 chlorobenzoyl)hydrazone 1,2 o isopropylidene alpha dextro xylopentadialdo 1,4 furanose(4 bromobenzoyl)hydrazone 1,2 o isopropylidene alpha dextro xylopentadialdo 1,4 furanose(4 chlorobenzoyl)hydrazone 1,2,4 triazolyl 3 thione 1,3,4 oxadiazole derivative 2 (1,2 o isopropylidene alpha dextro xylo tetrafuranos 4 yl) 5 (2 bromophenyl) 1,3,4 oxadiazole 2 (1,2 o isopropylidene alpha dextro xylo tetrafuranos 4 yl) 5 (2 chlorophenyl) 1,3,4 oxadiazole 2 (1,2 o isopropylidene alpha dextro xylo tetrafuranos 4 yl) 5 (3 bromophenyl) 1,3,4 oxadiazole 2 (1,2 o isopropylidene alpha dextro xylo tetrafuranos 4 yl) 5 (3 chlorophenyl) 1,3,4 oxadiazole 2 (1,2 o isopropylidene alpha dextro xylo tetrafuranos 4 yl) 5 (4 bromophenyl) 1,3,4 oxadiazole 2 (1,2 o isopropylidene alpha dextro xylo tetrafuranos 4 yl) 5 (4 chlorophenyl) 1,3,4 oxadiazole 3 (4 bromobenzoyl) 5 (1,2 o isopropylidene 3 o methyl alpha dextro xylofuranos 5 ulo 5 yl)imidazo[2,1 b]thiazole 3 (4 bromobenzoyl) 5 (1,2 o isopropylidene 3 o methyl alpha dextro xylofuranos 5 ulos 5 yl)imidazo[2,1 b]thiazole 3 benzoyl 5 (1,2 o isopropylidene 3 o methyl alpha dextro xylofuranos 5 ulo 5 yl)imidazo[2,1-b]thiazole 3,5 di o acetyl 6 deoxy 1,2 isopropylidene 6 [(4 bromobenzohydrazinecarbothionyl)amino]alpha dextro glucofuranose 5 (4 clorophenyl) 4 (1,2 o isopropylidene alpha dextro glucofuranos 6 yl) 1,2,4 triazoline 3 thione 6 bromo 5 deoxy 1,2 o isopropylidene 3 o methyl alpha dextro xylo hexofuranos 5 ulose 6 bromo 6 deoxy 1,2 o isopropylidene 3 o methyl alpha dextro glucofuranose antivirus agent imidazo[2,1 b]thiazole derivative n (5 benzoylthiazol 2 yl) n,n dimethylformamidine n' (5 4 bromobenzoylthiazol 2 yl) n,n dimethylformamidine unclassified drug animal cell antiviral activity article carbon nuclear magnetic resonance Dengue virus drug structure drug synthesis Junin virus nonhuman priority journal proton nuclear magnetic resonance structure activity relation Vero cell Animals Antiviral Agents Azoles Carbohydrates Cercopithecus aethiops Dengue Virus Inhibitory Concentration 50 Junin virus Toxicity Tests Vero Cells Junin virus |
| description |
Herein we describe the synthesis of 1,2,4-triazolyl-3-thione;1,3,4-oxadiazole, and imidazo[2,1-b]thiazole derivatives from carbohydrates. The antiviral activity of these compounds was tested against Dengue and Junin virus (the etiological agent of Argentine hemorrhagic fever). The 3-(p-bromobenzoyl)-5-(1,2-O-isopropylidene-3-O-methyl-α-d-xylofuranos-5-ulos-5-yl)imidazo[2,1-b]thiazole was able to inhibit the replication of both viruses in Vero cells at concentration significantly lower than the CC50. © 2008 Elsevier Ltd. All rights reserved. |
| format |
JOUR |
| author |
Barradas, J.S. Errea, M.I. D'Accorso, N.B. Sepúlveda, C.S. Talarico, L.B. Damonte, E.B. |
| author_facet |
Barradas, J.S. Errea, M.I. D'Accorso, N.B. Sepúlveda, C.S. Talarico, L.B. Damonte, E.B. |
| author_sort |
Barradas, J.S. |
| title |
Synthesis and antiviral activity of azoles obtained from carbohydrates |
| title_short |
Synthesis and antiviral activity of azoles obtained from carbohydrates |
| title_full |
Synthesis and antiviral activity of azoles obtained from carbohydrates |
| title_fullStr |
Synthesis and antiviral activity of azoles obtained from carbohydrates |
| title_full_unstemmed |
Synthesis and antiviral activity of azoles obtained from carbohydrates |
| title_sort |
synthesis and antiviral activity of azoles obtained from carbohydrates |
| url |
http://hdl.handle.net/20.500.12110/paper_00086215_v343_n14_p2468_Barradas |
| work_keys_str_mv |
AT barradasjs synthesisandantiviralactivityofazolesobtainedfromcarbohydrates AT erreami synthesisandantiviralactivityofazolesobtainedfromcarbohydrates AT daccorsonb synthesisandantiviralactivityofazolesobtainedfromcarbohydrates AT sepulvedacs synthesisandantiviralactivityofazolesobtainedfromcarbohydrates AT talaricolb synthesisandantiviralactivityofazolesobtainedfromcarbohydrates AT damonteeb synthesisandantiviralactivityofazolesobtainedfromcarbohydrates |
| _version_ |
1807319357742645248 |
| spelling |
todo:paper_00086215_v343_n14_p2468_Barradas2023-10-03T14:07:18Z Synthesis and antiviral activity of azoles obtained from carbohydrates Barradas, J.S. Errea, M.I. D'Accorso, N.B. Sepúlveda, C.S. Talarico, L.B. Damonte, E.B. 1,2,4-Triazolyl-3-thione 1,3,4-Oxadiazole Antiviral activity Carbohydrates Imidazo[2,1-b]thiazole Arsenic compounds Biomolecules Carbohydrates Chlorine compounds Concentration (process) Organic compounds Viruses 1,2,4-Triazolyl-3-thione 1,3,4-Oxadiazole Antiviral activities Antiviral activity Etiological agents Imidazo[2,1-b]thiazole Isopropylidene Junin virus Thiazole derivatives Vero cells Complexation 1,2 o isopropylidene alpha dextro xylopentadialdo 1,4 furanose(2 bromobenzoyl)hydrazone 1,2 o isopropylidene alpha dextro xylopentadialdo 1,4 furanose(2 chlorobenzoyl)hydrazone 1,2 o isopropylidene alpha dextro xylopentadialdo 1,4 furanose(3 bromobenzoyl)hydrazone 1,2 o isopropylidene alpha dextro xylopentadialdo 1,4 furanose(3 chlorobenzoyl)hydrazone 1,2 o isopropylidene alpha dextro xylopentadialdo 1,4 furanose(4 bromobenzoyl)hydrazone 1,2 o isopropylidene alpha dextro xylopentadialdo 1,4 furanose(4 chlorobenzoyl)hydrazone 1,2,4 triazolyl 3 thione 1,3,4 oxadiazole derivative 2 (1,2 o isopropylidene alpha dextro xylo tetrafuranos 4 yl) 5 (2 bromophenyl) 1,3,4 oxadiazole 2 (1,2 o isopropylidene alpha dextro xylo tetrafuranos 4 yl) 5 (2 chlorophenyl) 1,3,4 oxadiazole 2 (1,2 o isopropylidene alpha dextro xylo tetrafuranos 4 yl) 5 (3 bromophenyl) 1,3,4 oxadiazole 2 (1,2 o isopropylidene alpha dextro xylo tetrafuranos 4 yl) 5 (3 chlorophenyl) 1,3,4 oxadiazole 2 (1,2 o isopropylidene alpha dextro xylo tetrafuranos 4 yl) 5 (4 bromophenyl) 1,3,4 oxadiazole 2 (1,2 o isopropylidene alpha dextro xylo tetrafuranos 4 yl) 5 (4 chlorophenyl) 1,3,4 oxadiazole 3 (4 bromobenzoyl) 5 (1,2 o isopropylidene 3 o methyl alpha dextro xylofuranos 5 ulo 5 yl)imidazo[2,1 b]thiazole 3 (4 bromobenzoyl) 5 (1,2 o isopropylidene 3 o methyl alpha dextro xylofuranos 5 ulos 5 yl)imidazo[2,1 b]thiazole 3 benzoyl 5 (1,2 o isopropylidene 3 o methyl alpha dextro xylofuranos 5 ulo 5 yl)imidazo[2,1-b]thiazole 3,5 di o acetyl 6 deoxy 1,2 isopropylidene 6 [(4 bromobenzohydrazinecarbothionyl)amino]alpha dextro glucofuranose 5 (4 clorophenyl) 4 (1,2 o isopropylidene alpha dextro glucofuranos 6 yl) 1,2,4 triazoline 3 thione 6 bromo 5 deoxy 1,2 o isopropylidene 3 o methyl alpha dextro xylo hexofuranos 5 ulose 6 bromo 6 deoxy 1,2 o isopropylidene 3 o methyl alpha dextro glucofuranose antivirus agent imidazo[2,1 b]thiazole derivative n (5 benzoylthiazol 2 yl) n,n dimethylformamidine n' (5 4 bromobenzoylthiazol 2 yl) n,n dimethylformamidine unclassified drug animal cell antiviral activity article carbon nuclear magnetic resonance Dengue virus drug structure drug synthesis Junin virus nonhuman priority journal proton nuclear magnetic resonance structure activity relation Vero cell Animals Antiviral Agents Azoles Carbohydrates Cercopithecus aethiops Dengue Virus Inhibitory Concentration 50 Junin virus Toxicity Tests Vero Cells Junin virus Herein we describe the synthesis of 1,2,4-triazolyl-3-thione;1,3,4-oxadiazole, and imidazo[2,1-b]thiazole derivatives from carbohydrates. The antiviral activity of these compounds was tested against Dengue and Junin virus (the etiological agent of Argentine hemorrhagic fever). The 3-(p-bromobenzoyl)-5-(1,2-O-isopropylidene-3-O-methyl-α-d-xylofuranos-5-ulos-5-yl)imidazo[2,1-b]thiazole was able to inhibit the replication of both viruses in Vero cells at concentration significantly lower than the CC50. © 2008 Elsevier Ltd. All rights reserved. Fil:Barradas, J.S. 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. Fil:Sepúlveda, C.S. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Talarico, L.B. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Damonte, E.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_00086215_v343_n14_p2468_Barradas |