334477-08-6Relevant articles and documents
Iridium-Catalyzed Asymmetric Hydrogenation of Unsaturated Piperazin-2-ones
Wang, Yanzhao,Liu, Yuanyuan,Li, Kun,Yang, Guoqiang,Zhang, Wanbin
supporting information, p. 1933 - 1941 (2017/06/09)
Two different iridium catalyst systems, generated from the ruthenocene-based phosphine-oxazoline ligand tBu-mono-RuPHOX or the diphosphine ligand BINAP, were developed for the asymmetric hydrogenation of 5,6-dihydropyrazin-2(1H)-ones, affording chiral piperazin-2-ones in good yields and with moderate to good ees. Different catalytic behaviors for the hydrogenation of these types of substrate were observed with these two catalyst systems. Our tBu-mono-RuPHOX ligand, which bears a ruthenocene scaffold with planar chirality, was found to be the best ligand for the [Ir(L)(COD)]BArF catalyst system, affording the desired products with up to 94% ee. (Figure presented.).
Discovery of novel 2-(3-phenylpiperazin-1-yl)-pyrimidin-4-ones as glycogen synthase kinase-3β inhibitors
Usui, Yoshihiro,Uehara, Fumiaki,Hiki, Shinsuke,Watanabe, Kazutoshi,Tanaka, Hiroshi,Shouda, Aya,Yokoshima, Satoshi,Aritomo, Keiichi,Adachi, Takashi,Fukunaga, Kenji,Sunada, Shinji,Nabeno, Mika,Saito, Ken-Ichi,Eguchi, Jun-ichi,Yamagami, Keiji,Asano, Shouichi,Tanaka, Shinji,Yuki, Satoshi,Yoshii, Narihiko,Fujimura, Masatake,Horikawa, Takashi
, p. 3726 - 3732 (2017/07/27)
We herein describe the results of further evolution of glycogen synthase kinase (GSK)-3β inhibitors from our promising compounds containing a 2-phenylmorpholine moiety. Transformation of the morpholine moiety into a piperazine moiety resulted in potent GSK-3β inhibitors. SAR studies focused on the phenyl moiety revealed that a 4-fluoro-2-methoxy group afforded potent inhibitory activity toward GSK-3β. Based on docking studies, new hydrogen bonding between the nitrogen atom of the piperazine moiety and the oxygen atom of the main chain of Gln185 has been indicated, which may contribute to increased activity compared with that of the corresponding phenylmorpholine analogues. Effect of the stereochemistry of the phenylpiperazine moiety is also discussed.
Discovery process and pharmacological characterization of 2-(S)-(4-fluoro-2-methylphenyl)piperazine-1-carboxylic acid [1-(R)-(3,5-bis- trifluoromethylphenyl)ethyl]methylamide (vestipitant) as a potent, selective, and orally active NK1 receptor
Di Fabio, Romano,Griffante, Cristiana,Alvaro, Giuseppe,Pentassuglia, Giorgio,Pizzi, Domenica A.,Donati, Daniele,Rossi, Tino,Guercio, Giuseppe,Mattioli, Mario,Cimarosti, Zadeo,Marchioro, Carla,Provera, Stefano,Zonzini, Laura,Montanari, Dino,Melotto, Sergio,Gerrard, Philip A.,Trist, David G.,Ratti, Emiliangelo,Corsi, Mauro
experimental part, p. 3238 - 3247 (2010/04/03)
In an effort to discover novel druglike NK1 receptor antagonists a new series of suitably substituted C-phenylpiperazine derivatives was identified by an appropriate chemical exploration of related N-phenylpiperazine analogues, with the specifi
Synthesis of the NK1 receptor antagonist GW597599. Part 3: Development of a scalable route to a key chirally pure arylpiperazine urea, a happy end
Guercio, Giuseppe,Bacchi, Sergio,Perboni, Alcide,Leroi, Corinne,Tinazzi, Francesco,Bientinesi, Ilaria,Hourdin, Marie,Goodyear, Michael,Curti, Stefano,Provera, Stefano,Cimarosti, Zadeo
scheme or table, p. 1100 - 1110 (2010/04/22)
GW597599 1 is a novel NK-1 antagonist currently under investigation for the treatment of central nervous system disorders and emesis. The initial chemical development synthetic route, derived from the one used by medicinal chemistry, involved several haza
Synthesis of the NK1 receptor antagonist GW597599. Part 1: development of a scalable route to a key chirally pure arylpiperazine
Guercio, Giuseppe,Bacchi, Sergio,Goodyear, Michael,Carangio, Antonella,Tinazzi, Francesco,Curti, Stefano
, p. 1188 - 1194 (2013/01/03)
GW5975991 is a novel NK-1 antagonist currently under investigation for the treatment of CNS disorders and emesis. The initial synthetic route devised from the medicinal chemistry one, used several hazardous reagents, gave low yields, and produced high lev
