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: | , , , , , |
|---|---|
| Publicado: |
2008
|
| Materias: | |
| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v343_n14_p2468_Barradas http://hdl.handle.net/20.500.12110/paper_00086215_v343_n14_p2468_Barradas |
| Aporte de: |
| id |
paper: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, José Sebastián Errea, María Inés D'Accorso, Norma Beatriz Sepúlveda, Claudia Soledad Talarico, Laura Beatriz Damonte, Elsa Beatriz 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. |
| author |
Barradas, José Sebastián Errea, María Inés D'Accorso, Norma Beatriz Sepúlveda, Claudia Soledad Talarico, Laura Beatriz Damonte, Elsa Beatriz |
| author_facet |
Barradas, José Sebastián Errea, María Inés D'Accorso, Norma Beatriz Sepúlveda, Claudia Soledad Talarico, Laura Beatriz Damonte, Elsa Beatriz |
| author_sort |
Barradas, José Sebastián |
| 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 |
| publishDate |
2008 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v343_n14_p2468_Barradas http://hdl.handle.net/20.500.12110/paper_00086215_v343_n14_p2468_Barradas |
| work_keys_str_mv |
AT barradasjosesebastian synthesisandantiviralactivityofazolesobtainedfromcarbohydrates AT erreamariaines synthesisandantiviralactivityofazolesobtainedfromcarbohydrates AT daccorsonormabeatriz synthesisandantiviralactivityofazolesobtainedfromcarbohydrates AT sepulvedaclaudiasoledad synthesisandantiviralactivityofazolesobtainedfromcarbohydrates AT talaricolaurabeatriz synthesisandantiviralactivityofazolesobtainedfromcarbohydrates AT damonteelsabeatriz synthesisandantiviralactivityofazolesobtainedfromcarbohydrates |
| _version_ |
1768542625705492480 |
| spelling |
paper:paper_00086215_v343_n14_p2468_Barradas2023-06-08T14:32:55Z Synthesis and antiviral activity of azoles obtained from carbohydrates Barradas, José Sebastián Errea, María Inés D'Accorso, Norma Beatriz Sepúlveda, Claudia Soledad Talarico, Laura Beatriz Damonte, Elsa Beatriz 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. 2008 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v343_n14_p2468_Barradas http://hdl.handle.net/20.500.12110/paper_00086215_v343_n14_p2468_Barradas |