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)...

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Detalles Bibliográficos
Autores principales: Barradas, José Sebastián, Errea, María Inés, D'Accorso, Norma Beatriz, Sepúlveda, Claudia Soledad, Talarico, Laura Beatriz, Damonte, Elsa Beatriz
Publicado: 2008
Materias:
1,2,4-Triazolyl-3-thione
1,3,4-Oxadiazole
Antiviral activity
Carbohydrates
Imidazo[2,1-b]thiazole
Arsenic compounds
Biomolecules
Chlorine compounds
Concentration (process)
Organic compounds
Viruses
Antiviral activities
Etiological agents
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
nonhuman
priority journal
proton nuclear magnetic resonance
structure activity relation
Vero cell
Animals
Antiviral Agents
Azoles
Cercopithecus aethiops
Dengue Virus
Inhibitory Concentration 50
Toxicity Tests
Vero Cells
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:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
Descripción
Sumario: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.

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