112606-39-0Relevant academic research and scientific papers
A New, One-Pot, Multicomponent Synthesis of Bioactive N -Pyrazolylformamidines under Microwave Irradiation
Lim, Felicia Phei Lin,Luna, Giuseppe,Dolzhenko, Anton V.
, p. 2423 - 2428 (2016/07/28)
A one-pot, three-component, microwave-assisted reaction of polysubstituted 5-aminopyrazoles, triethyl orthoformate, and a series of cyclic secondary amines was developed and successfully employed for the synthesis of novel N-pyrazolylformamidines. Under c
A one-pot, three-component aminotriazine annulation onto 5-aminopyrazole-4-carbonitriles under microwave irradiation
Lim, Felicia Phei Lin,Luna, Giuseppe,Dolzhenko, Anton V.
, p. 521 - 524 (2015/02/19)
A one-pot, three-component, microwave-assisted reaction of 5-aminopyrazole-4-carbonitriles, triethyl orthoformate and cyanamide afforded novel 7-arylamino-substituted 4-aminopyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles. The reaction proceeded in a chemo- and regioselective manner resulting in the successful amino-1,3,5-triazine annulation onto 5-aminopyrazole-4-carbonitriles to give 4-aminopyrazolo[1,5-a][1,3,5]triazine-8-carbonitriles. The operational simplicity of the method and high purity of the products, which can be isolated via simple filtration, make this approach attractive for the preparation of a library of compounds for drug discovery processes.
Pyrazolopyrimidines: Potent Inhibitors Targeting the Capsid of Rhino- and Enteroviruses
Makarov, Vadim A.,Braun, Heike,Richter, Martina,Riabova, Olga B.,Kirchmair, Johannes,Kazakova, Elena S.,Seidel, Nora,Wutzler, Peter,Schmidtke, Michaela
supporting information, p. 1629 - 1634 (2015/10/06)
There are currently no drugs available for the treatment of enterovirus (EV)-induced acute and chronic diseases such as the common cold, meningitis, encephalitis, pneumonia, and myocarditis with or without consecutive dilated cardiomyopathy. Here, we report the discovery and characterization of pyrazolopyrimidines, a well-tolerated and potent class of novel EV inhibitors. The compounds inhibit the replication of a broad spectrum of EV in vitro with IC50 values between 0.04 and 0.64 μM for viruses resistant to pleconaril, a known capsid-binding inhibitor, without affecting cytochrome P450 enzyme activity. Using virological and genetics methods, the viral capsid was identified as the target of the most promising, orally bioavailable compound 3-(4-trifluoromethylphenyl)amino-6-phenylpyrazolo[3,4-d]pyrimidine-4-amine (OBR-5-340). Its prophylactic as well as therapeutic application was proved for coxsackievirus B3-induced chronic myocarditis in mice. The favorable pharmacokinetic, toxicological, and pharmacodynamics profile in mice renders OBR-5-340 a highly promising drug candidate, and the regulatory nonclinical program is ongoing. Curing the common cold! A cluster of pyrazolopyrimidines with potent broad-spectrum activity against enteroviruses was discovered. Extensive structure-property relationship analyses led to the identification of 3-(4-trifluoromethyl-phenyl)amino-6-phenylpyrazolo[3,4-d]pyrimidine-4-amine, shown to be a blocker of the viral capsid protein, as a lead compound for drug development with favorable physicochemical, pharmacokinetic, and toxicological properties.
Discovery of novel 2-anilinopyrazolo[1,5-a]pyrimidine derivatives as c-Src kinase inhibitors for the treatment of acute ischemic stroke
Mukaiyama, Harunobu,Nishimura, Toshihiro,Shiohara, Hiroaki,Kobayashi, Satoko,Komatsu, Yoshimitsu,Kikuchi, Shinji,Tsuji, Eiichi,Kamada, Noboru,Ohnota, Hideki,Kusama, Hiroshi
, p. 881 - 889 (2008/02/08)
We synthesized a series of novel 2-anilinopyrazolo[1,5-a]pyrimidine derivatives and evaluated their ability to inhibit c-Src kinase; 7-(2-amino-2-methylpropylamino)-5-cyclopropyl-2-(3,5-dimethoxyphenylamino) pyrazolo-[1,5-a]pyrimidine-3-carboxamide 7o and
Synthesis and antimalarial activity of substituted pyrazole derivatives
Dominguez, Jose N.,Charris, Jaime E.,Caparelli, Mario,Riggione, Flavia
, p. 482 - 488 (2007/10/03)
The development of new antimalarial drugs is an urgent priority considering the increasing prevalence of drug-resistant Plasmodium falciparum parasites. A series of pyrazoles are described as part of efforts directed toward the synthesis of some potent an
Use of a pharmacophore model for the design of EGF-R tyrosine kinase inhibitors: 4-(Phenylamino)pyrazolo[3,4-d]pyrimidines
Traxler, Peter,Bold, Guido,Frei, Joerg,Lang, Marc,Lydon, Nicholas,Mett, Helmut,Buchdunger, Elisabeth,Meyer, Thomas,Mueller, Marcel,Furet, Pascal
, p. 3601 - 3616 (2007/10/03)
In the course of the random screening of a pool of CIBA chemicals, the two pyrazolopyrimidines 1 and 2 have been identified as fairly potent inhibitors of the EGF-R tyrosine kinase. Using a pharmacophore model for ATP- competitive inhibitors interacting w
Free Radical Reactions of N-Heterocyclic Compounds, XIV. - Oxidative Cyclization of Anilinopyrazoles to Pyrazolobenzimidazoles
Kluge, Ralph,Schulz, Manfred,Pobisova, Miroslava,Nuechter, Matthias
, p. 1729 - 1734 (2007/10/02)
Substituted Anilinopyrazoles 1 were oxidized by dibenzoyl peroxide or lead(IV) oxide.Different oxidation products were isolated depending on the substituents in the anilino group of anilinopyrazoles 1.Intermediate pyrazolyl radicals 5, which could be trap
