191353-20-5Relevant articles and documents
Discovery, SAR study and ADME properties of methyl 4-amino-3-cyano-1-(2-benzyloxyphenyl)-1H-pyrazole-5-carboxylate as an HIV-1 replication inhibitor
Alvarez, Karine,Busca, Patricia,Calvez, Vincent,Delelis, Olivier,Fichez, Jeanne,Gizzi, Patrick,Gravier-Pelletier, Christine,Le Corre, Laurent,Prestat, Guillaume,Sayon, Sophie,Soulie, Cathia,Marcelin, Anne-Geneviève,Priet, Stéphane
, p. 577 - 582 (2020/06/04)
Inspired by the antiviral activity of known pyrazole-based HIV inhibitors, we screened our in-house library of pyrazole-based compounds to evaluate theirin celluloactivity against HIV-1 replication. Two hits with very similar structures appeared from single and multiple-round infection assays to be non-toxic and active in a dose-dependent manner. Chemical expansion of their series allowed an in-depth and consistent structure-activity-relationship study (SAR) to be built. Further ADME evaluation led to the selection of 4-amino-3-cyano-1-(2-benzyloxyphenyl)-1H-pyrazole-5-carboxylate with an advantageous pharmacokinetic profile. Finally, examination of its mode of action revealed that this compound does not belong to the three main classes of anti-HIV drugs, a feature of prime interest in the context of viral resistance.
Microwave-assisted preparation of 4-amino-3-cyano-5-methoxycarbonyl-N-arylpyrazoles as building blocks for the diversity-oriented synthesis of pyrazole-based polycyclic scaffolds
Corre, Laurent Le,Tak-Tak, Lotfi,Guillard, Arthur,Prestat, Guillaume,Gravier-Pelletier, Christine,Busca, Patricia
, p. 409 - 423 (2015/02/02)
The synthesis of 4-amino-3-cyano-N-arylpyrazoles A based on a Thorpe-Ziegler cyclization as the key step has been achieved using microwave activation. Via a new diversity-oriented synthetic pathway, these highly functionalized building blocks allowed the access to various heteroaromatic scaffolds such as pyrazolo-pyridines B, pyrazolo-pyrimidines C and pyrazolo-oxadiazoles D. Interestingly, these platforms contain three to four reactive sites that could be used for post-functionalization in order to further increase the molecular diversity.
Synthesis of novel derivatives of 4-amino-3,5-dicyanopyrazole
Goncalves, M. Sameiro T.,Oliveira-Campos, Ana M.F.,Rodrigues, Ligia M.,Proenca, M. Fernanda R.P.,Griffiths, John,Maia, Hernani L.S.,Kaja, Martin,Hrdina, Radim
, p. 115 - 117 (2007/10/03)
Diazotisation of substituted arylamines followed by reaction with malononitrile gave substituted arylazomalononitriles. Cyclisation of these intermediates with chloroacetonitrile and triethylamine, as base, gave the corresponding new aminoclicyanopyrazoles, in 22-80% yields.
