Synthesis and evaluation of 1,1′-hydrocarbylenebis(indazol-3-ols) as potential antimalarial drugs
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 d...
Guardado en:
| Publicado: |
2009
|
|---|---|
| Materias: | |
| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_18607179_v4_n1_p78_Alho http://hdl.handle.net/20.500.12110/paper_18607179_v4_n1_p78_Alho |
| Aporte de: |
| id |
paper:paper_18607179_v4_n1_p78_Alho |
|---|---|
| record_format |
dspace |
| spelling |
paper:paper_18607179_v4_n1_p78_Alho2023-06-08T16:29:29Z Synthesis and evaluation of 1,1′-hydrocarbylenebis(indazol-3-ols) as potential antimalarial drugs 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 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. 2009 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_18607179_v4_n1_p78_Alho http://hdl.handle.net/20.500.12110/paper_18607179_v4_n1_p78_Alho |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
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 |
| spellingShingle |
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 Synthesis and evaluation of 1,1′-hydrocarbylenebis(indazol-3-ols) as potential antimalarial drugs |
| topic_facet |
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 |
| description |
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. |
| title |
Synthesis and evaluation of 1,1′-hydrocarbylenebis(indazol-3-ols) as potential antimalarial drugs |
| title_short |
Synthesis and evaluation of 1,1′-hydrocarbylenebis(indazol-3-ols) as potential antimalarial drugs |
| title_full |
Synthesis and evaluation of 1,1′-hydrocarbylenebis(indazol-3-ols) as potential antimalarial drugs |
| title_fullStr |
Synthesis and evaluation of 1,1′-hydrocarbylenebis(indazol-3-ols) as potential antimalarial drugs |
| title_full_unstemmed |
Synthesis and evaluation of 1,1′-hydrocarbylenebis(indazol-3-ols) as potential antimalarial drugs |
| title_sort |
synthesis and evaluation of 1,1′-hydrocarbylenebis(indazol-3-ols) as potential antimalarial drugs |
| publishDate |
2009 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_18607179_v4_n1_p78_Alho http://hdl.handle.net/20.500.12110/paper_18607179_v4_n1_p78_Alho |
| _version_ |
1768542860090540032 |