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Abstract:

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.

Registro:

Documento: Artículo
Título:Imidazo[2,1-b]thiazole carbohydrate derivatives: Synthesis and antiviral activity against Junin virus, agent of Argentine hemorrhagic fever
Autor:Barradas, J.S.; Errea, M.I.; D'Accorso, N.B.; Sepúlveda, C.S.; Damonte, E.B.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina
Instituto Tecnológico de Buenos Aires, Avda. Eduardo Madero 399, 1106, Buenos Aires, Argentina
Laboratorio de Virología - Departamento de Biológica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina
Palabras clave: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
Año:2011
Volumen:46
Número:1
Página de inicio:259
Página de fin:264
DOI: http://dx.doi.org/10.1016/j.ejmech.2010.11.012
Título revista:European Journal of Medicinal Chemistry
Título revista abreviado:Eur. J. Med. Chem.
ISSN:02235234
CODEN:EJMCA
CAS:ribavirin, 36791-04-5; Antiviral Agents; Carbohydrates; Thiazoles
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_02235234_v46_n1_p259_Barradas

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Citas:

---------- APA ----------
Barradas, J.S., Errea, M.I., D'Accorso, N.B., Sepúlveda, C.S. & Damonte, E.B. (2011) . Imidazo[2,1-b]thiazole carbohydrate derivatives: Synthesis and antiviral activity against Junin virus, agent of Argentine hemorrhagic fever. European Journal of Medicinal Chemistry, 46(1), 259-264.
http://dx.doi.org/10.1016/j.ejmech.2010.11.012
---------- CHICAGO ----------
Barradas, J.S., Errea, M.I., D'Accorso, N.B., Sepúlveda, C.S., Damonte, E.B. "Imidazo[2,1-b]thiazole carbohydrate derivatives: Synthesis and antiviral activity against Junin virus, agent of Argentine hemorrhagic fever" . European Journal of Medicinal Chemistry 46, no. 1 (2011) : 259-264.
http://dx.doi.org/10.1016/j.ejmech.2010.11.012
---------- MLA ----------
Barradas, J.S., Errea, M.I., D'Accorso, N.B., Sepúlveda, C.S., Damonte, E.B. "Imidazo[2,1-b]thiazole carbohydrate derivatives: Synthesis and antiviral activity against Junin virus, agent of Argentine hemorrhagic fever" . European Journal of Medicinal Chemistry, vol. 46, no. 1, 2011, pp. 259-264.
http://dx.doi.org/10.1016/j.ejmech.2010.11.012
---------- VANCOUVER ----------
Barradas, J.S., Errea, M.I., D'Accorso, N.B., Sepúlveda, C.S., Damonte, E.B. Imidazo[2,1-b]thiazole carbohydrate derivatives: Synthesis and antiviral activity against Junin virus, agent of Argentine hemorrhagic fever. Eur. J. Med. Chem. 2011;46(1):259-264.
http://dx.doi.org/10.1016/j.ejmech.2010.11.012