Imidazo[2,1-b]thiazole carbohydrate derivatives: Synthesis and antiviral activity against Junin virus, agent of Argentine hemorrhagic fever

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Herein, we describe the syntheses of 3,5-disubstituted imidazo[2,1-b] thiazole. The cyclization step was performed in two different conditions by using either thermal or microwave heating. Comparing the results of both methodologies, we found that the microwave assistance is an improved alternative...

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Autores principales:	Barradas, José Sebastián, Errea, María Inés, D'Accorso, Norma Beatriz, Sepúlveda, Claudia Soledad, Damonte, Elsa Beatriz
Publicado:	2011
Materias:	Antiviral activity Carbohydrates Imidazo[2,1-b]thiazole Junin virus (JUNV) Microwave irradiation 3 (2 bromobenzoyl) 5 (3 o acetyl 1,2 o isopropylidene 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 ulo 5 yl)imidazo[2,1 b]thiazole 3 (4 chlorobenzoyl) 5 (1,2 o isopropylidene 3 o methyl alpha dextro xylofuranos 5 ulo 5 yl)imidazo[2,1 b]thiazole 3 (4 fluorobenzoyl) 5 (1,2 o isopropylidene 3 o methyl alpha dextro xylofuranos 5 ulo 5 yl)imidazo[2,1 b]thiazole 3 (benzoyl) 5 (3 o acetyl 1,2 o isopropylidene alpha dextro xylofuranos 5 ulo 5 yl)imidazo[2,1 b]thiazole antivirus agent carbohydrate derivative heterocyclic compound imidazo[2,1 b]thiazole carbohydrate derivative ribavirin thiazole derivative unclassified drug animal cell antiviral activity Argentine hemorrhagic fever article cyclization cytotoxicity drug structure drug synthesis human human cell Junin virus microwave radiation nonhuman thermal analysis virus strain Animals Antiviral Agents Cercopithecus aethiops Hemorrhagic Fever, American Inhibitory Concentration 50 Thiazoles Vero Cells
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_02235234_v46_n1_p259_Barradas http://hdl.handle.net/20.500.12110/paper_02235234_v46_n1_p259_Barradas
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

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spelling	paper:paper_02235234_v46_n1_p259_Barradas2023-06-08T15:21:43Z Imidazo[2,1-b]thiazole carbohydrate derivatives: Synthesis and antiviral activity against Junin virus, agent of Argentine hemorrhagic fever Barradas, José Sebastián Errea, María Inés D'Accorso, Norma Beatriz Sepúlveda, Claudia Soledad Damonte, Elsa Beatriz Antiviral activity Carbohydrates Imidazo[2,1-b]thiazole Junin virus (JUNV) Microwave irradiation 3 (2 bromobenzoyl) 5 (3 o acetyl 1,2 o isopropylidene 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 ulo 5 yl)imidazo[2,1 b]thiazole 3 (4 chlorobenzoyl) 5 (1,2 o isopropylidene 3 o methyl alpha dextro xylofuranos 5 ulo 5 yl)imidazo[2,1 b]thiazole 3 (4 fluorobenzoyl) 5 (1,2 o isopropylidene 3 o methyl alpha dextro xylofuranos 5 ulo 5 yl)imidazo[2,1 b]thiazole 3 (benzoyl) 5 (3 o acetyl 1,2 o isopropylidene alpha dextro xylofuranos 5 ulo 5 yl)imidazo[2,1 b]thiazole antivirus agent carbohydrate derivative heterocyclic compound imidazo[2,1 b]thiazole carbohydrate derivative ribavirin thiazole derivative unclassified drug animal cell antiviral activity Argentine hemorrhagic fever article cyclization cytotoxicity drug structure drug synthesis human human cell Junin virus microwave radiation nonhuman thermal analysis virus strain Animals Antiviral Agents Carbohydrates Cercopithecus aethiops Hemorrhagic Fever, American Inhibitory Concentration 50 Junin virus Thiazoles Vero Cells Herein, we describe the syntheses of 3,5-disubstituted imidazo[2,1-b] thiazole. The cyclization step was performed in two different conditions by using either thermal or microwave heating. Comparing the results of both methodologies, we found that the microwave assistance is an improved alternative to obtain this family of heterocyclic compound. Compounds were first evaluated for cytotoxicity in Vero cells by MTT method and then, the antiviral activity was assayed by a virus yield inhibition assay in the range of concentrations lower than the corresponding CC50, using JUNV strain IV4454 as the model system. The most active compounds (3 and 4), showed a level of antiviral activity against JUNV in monkey Vero cells better than the reference substance ribavirin. Then, they are promising lead compound for further analysis and characterization to establish their therapeutic potential against hemorrhagic fever viruses. 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:Damonte, E.B. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2011 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_02235234_v46_n1_p259_Barradas http://hdl.handle.net/20.500.12110/paper_02235234_v46_n1_p259_Barradas
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	Antiviral activity Carbohydrates Imidazo[2,1-b]thiazole Junin virus (JUNV) Microwave irradiation 3 (2 bromobenzoyl) 5 (3 o acetyl 1,2 o isopropylidene 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 ulo 5 yl)imidazo[2,1 b]thiazole 3 (4 chlorobenzoyl) 5 (1,2 o isopropylidene 3 o methyl alpha dextro xylofuranos 5 ulo 5 yl)imidazo[2,1 b]thiazole 3 (4 fluorobenzoyl) 5 (1,2 o isopropylidene 3 o methyl alpha dextro xylofuranos 5 ulo 5 yl)imidazo[2,1 b]thiazole 3 (benzoyl) 5 (3 o acetyl 1,2 o isopropylidene alpha dextro xylofuranos 5 ulo 5 yl)imidazo[2,1 b]thiazole antivirus agent carbohydrate derivative heterocyclic compound imidazo[2,1 b]thiazole carbohydrate derivative ribavirin thiazole derivative unclassified drug animal cell antiviral activity Argentine hemorrhagic fever article cyclization cytotoxicity drug structure drug synthesis human human cell Junin virus microwave radiation nonhuman thermal analysis virus strain Animals Antiviral Agents Carbohydrates Cercopithecus aethiops Hemorrhagic Fever, American Inhibitory Concentration 50 Junin virus Thiazoles Vero Cells
spellingShingle	Antiviral activity Carbohydrates Imidazo[2,1-b]thiazole Junin virus (JUNV) Microwave irradiation 3 (2 bromobenzoyl) 5 (3 o acetyl 1,2 o isopropylidene 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 ulo 5 yl)imidazo[2,1 b]thiazole 3 (4 chlorobenzoyl) 5 (1,2 o isopropylidene 3 o methyl alpha dextro xylofuranos 5 ulo 5 yl)imidazo[2,1 b]thiazole 3 (4 fluorobenzoyl) 5 (1,2 o isopropylidene 3 o methyl alpha dextro xylofuranos 5 ulo 5 yl)imidazo[2,1 b]thiazole 3 (benzoyl) 5 (3 o acetyl 1,2 o isopropylidene alpha dextro xylofuranos 5 ulo 5 yl)imidazo[2,1 b]thiazole antivirus agent carbohydrate derivative heterocyclic compound imidazo[2,1 b]thiazole carbohydrate derivative ribavirin thiazole derivative unclassified drug animal cell antiviral activity Argentine hemorrhagic fever article cyclization cytotoxicity drug structure drug synthesis human human cell Junin virus microwave radiation nonhuman thermal analysis virus strain Animals Antiviral Agents Carbohydrates Cercopithecus aethiops Hemorrhagic Fever, American Inhibitory Concentration 50 Junin virus Thiazoles Vero Cells Barradas, José Sebastián Errea, María Inés D'Accorso, Norma Beatriz Sepúlveda, Claudia Soledad Damonte, Elsa Beatriz Imidazo[2,1-b]thiazole carbohydrate derivatives: Synthesis and antiviral activity against Junin virus, agent of Argentine hemorrhagic fever
topic_facet	Antiviral activity Carbohydrates Imidazo[2,1-b]thiazole Junin virus (JUNV) Microwave irradiation 3 (2 bromobenzoyl) 5 (3 o acetyl 1,2 o isopropylidene 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 ulo 5 yl)imidazo[2,1 b]thiazole 3 (4 chlorobenzoyl) 5 (1,2 o isopropylidene 3 o methyl alpha dextro xylofuranos 5 ulo 5 yl)imidazo[2,1 b]thiazole 3 (4 fluorobenzoyl) 5 (1,2 o isopropylidene 3 o methyl alpha dextro xylofuranos 5 ulo 5 yl)imidazo[2,1 b]thiazole 3 (benzoyl) 5 (3 o acetyl 1,2 o isopropylidene alpha dextro xylofuranos 5 ulo 5 yl)imidazo[2,1 b]thiazole antivirus agent carbohydrate derivative heterocyclic compound imidazo[2,1 b]thiazole carbohydrate derivative ribavirin thiazole derivative unclassified drug animal cell antiviral activity Argentine hemorrhagic fever article cyclization cytotoxicity drug structure drug synthesis human human cell Junin virus microwave radiation nonhuman thermal analysis virus strain Animals Antiviral Agents Carbohydrates Cercopithecus aethiops Hemorrhagic Fever, American Inhibitory Concentration 50 Junin virus Thiazoles Vero Cells
description	Herein, we describe the syntheses of 3,5-disubstituted imidazo[2,1-b] thiazole. The cyclization step was performed in two different conditions by using either thermal or microwave heating. Comparing the results of both methodologies, we found that the microwave assistance is an improved alternative to obtain this family of heterocyclic compound. Compounds were first evaluated for cytotoxicity in Vero cells by MTT method and then, the antiviral activity was assayed by a virus yield inhibition assay in the range of concentrations lower than the corresponding CC50, using JUNV strain IV4454 as the model system. The most active compounds (3 and 4), showed a level of antiviral activity against JUNV in monkey Vero cells better than the reference substance ribavirin. Then, they are promising lead compound for further analysis and characterization to establish their therapeutic potential against hemorrhagic fever viruses.
author	Barradas, José Sebastián Errea, María Inés D'Accorso, Norma Beatriz Sepúlveda, Claudia Soledad Damonte, Elsa Beatriz
author_facet	Barradas, José Sebastián Errea, María Inés D'Accorso, Norma Beatriz Sepúlveda, Claudia Soledad Damonte, Elsa Beatriz
author_sort	Barradas, José Sebastián
title	Imidazo[2,1-b]thiazole carbohydrate derivatives: Synthesis and antiviral activity against Junin virus, agent of Argentine hemorrhagic fever
title_short	Imidazo[2,1-b]thiazole carbohydrate derivatives: Synthesis and antiviral activity against Junin virus, agent of Argentine hemorrhagic fever
title_full	Imidazo[2,1-b]thiazole carbohydrate derivatives: Synthesis and antiviral activity against Junin virus, agent of Argentine hemorrhagic fever
title_fullStr	Imidazo[2,1-b]thiazole carbohydrate derivatives: Synthesis and antiviral activity against Junin virus, agent of Argentine hemorrhagic fever
title_full_unstemmed	Imidazo[2,1-b]thiazole carbohydrate derivatives: Synthesis and antiviral activity against Junin virus, agent of Argentine hemorrhagic fever
title_sort	imidazo[2,1-b]thiazole carbohydrate derivatives: synthesis and antiviral activity against junin virus, agent of argentine hemorrhagic fever
publishDate	2011
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_02235234_v46_n1_p259_Barradas http://hdl.handle.net/20.500.12110/paper_02235234_v46_n1_p259_Barradas
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_version_	1768544954333790208

Imidazo[2,1-b]thiazole carbohydrate derivatives: Synthesis and antiviral activity against Junin virus, agent of Argentine hemorrhagic fever

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