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Título: | Fluorinated indazoles as novel selective inhibitors of nitric oxide synthase (NOS): Synthesis and biological evaluation |
Autor: | Claramunt, Rosa M.; López, C.; Pérez-Medina, Carlos; Pérez-Torralba, M.; Elguero, José CSIC ORCID; Escames, Germaine; Acuña-Castroviejo, D. | Fecha de publicación: | 2009 | Editor: | Pergamon Press | Citación: | Bioorganic and Medicinal Chemistry 17: 6180- 6187 (2009) | Resumen: | In order to find new compounds with neuroprotective activity and NOS-I/NOS-II selectivity, we have designed, synthesized, and characterized 14 new NOS inhibitors with an indazole structure. The first group corresponds to 4,5,6,7-tetrahydroindazoles (4-8), the second to the N-methyl derivatives (9-12) of 7-nitro-1H-indazole (1) and 3-bromo-7-nitro-1H-indazole (2), and the latter to 4,5,6,7-tetrafluoroindazoles (13-17). Compound 13 (4,5,6,7-tetrafluoro-3-methyl-1H-indazole) inhibited NOS-I by 63% and NOS-II by 83%. Interestingly, compound 16 (4,5,6,7-tetrafluoro-3-perfluorophenyl-1H-indazole) inhibited NOS-II activity by 80%, but it did not affect to NOS-I activity. Structural comparison between these new indazoles further supports the importance of the aromatic indazole skeleton for NOS inhibition and indicate that bulky groups or N-methylation of 1 and 2 diminish their effect on NOS activity. The fluorination of the aromatic ring increased the inhibitory potency and NOS-II selectivity, suggesting that this is a promising strategy for NOS selective inhibitors. © 2009. | Versión del editor: | http://dx.doi.org/10.1016/j.bmc.2009.07.067 | URI: | http://hdl.handle.net/10261/65681 | DOI: | 10.1016/j.bmc.2009.07.067 | Identificadores: | doi: 10.1016/j.bmc.2009.07.067 issn: 0968-0896 e-issn: 1464-3391 |
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