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Alho, M.M.; García-Sánchez, R.N.; Nogal-Ruiz, J.J.; Escario, J.A.; Gómez-Barrio, A.; Martínez-Fernández, A.R.; Arán, V.J. "Synthesis and evaluation of 1,1′-hydrocarbylenebis(indazol-3-ols) as potential antimalarial drugs" (2009) ChemMedChem. 4(1):78-87
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Abstract:

Bis(indazol-3-ol) derivatives (5, 30-38) were prepared by alkylation of 3-alkoxyindazoles with α,ω-dibromides, followed by removal of the O-protecting groups. These compounds were subsequently evaluated as inhibitors of biocrystallization of ferriproto-porphyrin IX (heme) to hemozoin, a Plasmodium detoxification specific process. Most bis(5-nitroindazol-3-ols) were good inhibitors, however, a denitro analogue (38), the intermediate bis(3-al-koxyindazoles) (15-29) as well as bis(indazolin-3-ones) (39-42) were not active, showing the importance of the NO2 and OH groups in the inhibition process. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Registro:

Documento: Artículo
Título:Synthesis and evaluation of 1,1′-hydrocarbylenebis(indazol-3-ols) as potential antimalarial drugs
Autor:Alho, M.M.; García-Sánchez, R.N.; Nogal-Ruiz, J.J.; Escario, J.A.; Gómez-Barrio, A.; Martínez-Fernández, A.R.; Arán, V.J.
Filiación:CIHIDECAR (CONICET), Departamento de Química Orgánica, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina
Departamento de Parasitología, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain
Nstituto de Química Médica (IQM), CSIC, c/Juan de la Cierva 3, 28006 Madrid, Spain
Palabras clave:Alkylation; Antimalarial agents; Drug design; Inhibitors; Nitrogen heterocycles; 1,1 hydrocarbylenebis(inidazol 3 ols); 1,1 tetramethylenebis(5 nitro 1h indazol 3 ol); 1,1' (2 xylylene)bis(1h indazol 3 ol); 1,1' (3 xylylene)bis(5 nitro 1h indazol 3 ol); 1,1' (4 xylylene)bis(5 nitro 1h indazol 3 ol); 1,1' [(2,2 diphenyldiyl)bismethylene]bis(5 nitro 1h indazol 3 ol); 1,1' [(2,6 pyridinediyl)bismethylene]bis(5 nitro 1h indazol 3 ol); 1,1' ethylenebis(5 nitro 1h indazol 3 ol); 1,1' hexamethylenebis(5 nitro 1h indazol 3 ol); 1,1' pentamethylenebis(5 nitro 1h indazol 3 ol); 3 alkoxyindazole derivative; alpha omega dibromide derivative; antimalarial agent; bis(5 nitroindazol ols); bromine derivative; hematin; hemozoin; indazole derivative; unclassified drug; alkylation; antimalarial activity; article; chemical reaction; detoxification; drug screening; drug structure; drug synthesis; Plasmodium; priority journal; Animals; Antimalarials; Hemeproteins; Hemin; Indazoles; Inhibitory Concentration 50; Mice; Plasmodium berghei
Año:2009
Volumen:4
Número:1
Página de inicio:78
Página de fin:87
DOI: http://dx.doi.org/10.1002/cmdc.200800176
Título revista:ChemMedChem
Título revista abreviado:ChemMedChem
ISSN:18607179
CAS:hematin, 15489-90-4; hemozoin, 39404-00-7; Antimalarials; Hemeproteins; Hemin, 16009-13-5; hemozoin, 39404-00-7; Indazoles
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_18607179_v4_n1_p78_Alho

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Citas:

---------- APA ----------
Alho, M.M., García-Sánchez, R.N., Nogal-Ruiz, J.J., Escario, J.A., Gómez-Barrio, A., Martínez-Fernández, A.R. & Arán, V.J. (2009) . Synthesis and evaluation of 1,1′-hydrocarbylenebis(indazol-3-ols) as potential antimalarial drugs. ChemMedChem, 4(1), 78-87.
http://dx.doi.org/10.1002/cmdc.200800176
---------- CHICAGO ----------
Alho, M.M., García-Sánchez, R.N., Nogal-Ruiz, J.J., Escario, J.A., Gómez-Barrio, A., Martínez-Fernández, A.R., et al. "Synthesis and evaluation of 1,1′-hydrocarbylenebis(indazol-3-ols) as potential antimalarial drugs" . ChemMedChem 4, no. 1 (2009) : 78-87.
http://dx.doi.org/10.1002/cmdc.200800176
---------- MLA ----------
Alho, M.M., García-Sánchez, R.N., Nogal-Ruiz, J.J., Escario, J.A., Gómez-Barrio, A., Martínez-Fernández, A.R., et al. "Synthesis and evaluation of 1,1′-hydrocarbylenebis(indazol-3-ols) as potential antimalarial drugs" . ChemMedChem, vol. 4, no. 1, 2009, pp. 78-87.
http://dx.doi.org/10.1002/cmdc.200800176
---------- VANCOUVER ----------
Alho, M.M., García-Sánchez, R.N., Nogal-Ruiz, J.J., Escario, J.A., Gómez-Barrio, A., Martínez-Fernández, A.R., et al. Synthesis and evaluation of 1,1′-hydrocarbylenebis(indazol-3-ols) as potential antimalarial drugs. ChemMedChem. 2009;4(1):78-87.
http://dx.doi.org/10.1002/cmdc.200800176