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Synthesis and pharmacological assessment of diversely substituted pyrazolo[3,4-b]quinoline, and benzo[b]pyrazolo[4,3-g][1,8]naphthyridine derivatives

AuthorsSilva, Daniel; Chioua, Mourad ; Samadi, Abdelouahid ; Carreiras, M. Carmo; Jimeno, M. Luisa ; Mendes, Eduarda; Ríos, Cristóbal de los; Romero, Alejandro ; Villarroya, Mercedes; Marco-Contelles, José
Issue Date2011
CitationEuropean Journal of Medicinal Chemistry 46 : 4676- 4681 (2011)
AbstractThe synthesis and pharmacological analyses of a number of pyrazolo[3,4-b]quinoline and benzo[b]pyrazolo[4,3-g][1,8]naphthyridine derivatives are reported. We have synthesized the diversely substituted tacrine analogues 1-6, by Friedländer-type reaction of readily available o-amino-1-methyl-pyrazole-dicarbonitriles with cyclohexanone. The biological evaluation showed that pyrazolotacrines 1-6 are inhibitors of Electrophorus electricus acetylcholinesterase (EeAChE), in the micromolar range, and quite selective in respect to serum horse butyrylcholinesterase (eqBuChE) inhibition; the most interesting inhibitor is N-(5-amino-1-methyl-6,7,8,9-tetrahydro-1H- benzo[b]pyrazolo[4,3-g][1,8]naphthyridin-3-yl)acetamide (5) [IC50 (EeAChE) = 0.069 ± 0.006 μM; IC50 (eqBuChE) = 6.3 ± 0.6 μM]. Kinetic studies showed that compound 5 is a mixed-type inhibitor of EeAChE (Ki = 155 nM). Inhibitor 5 showed a 45% neuroprotection value against rotenone/oligomycin A-induced neuronal death. © 2011 Elsevier Masson SAS. All rights reserved.
Identifiersdoi: 10.1016/j.ejmech.2011.05.068
issn: 0223-5234
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