156856-52-9Relevant academic research and scientific papers
New entries in Lewis acid-Lewis base bifunctional asymmetric catalyst: Catalytic enantioselective Reissert reaction of pyridine derivatives
Ichikawa, Eiko,Suzuki, Masato,Yabu, Kazuo,Albert, Matthias,Kanai, Motomu,Shibasaki, Masakatsu
, p. 11808 - 11809 (2004)
The first catalytic enantioselective Reissert reaction of pyridine derivatives that affords products with excellent regio- and enantioselectivity is described. The key for success is the development of new Lewis acid-Lewis base bifunctional asymmetric catalysts containing an aluminum as a Lewis acid and sulfoxides or phosphine sulfides as a Lewis base. These reactions are useful for the synthesis of a variety of chiral piperidine subunits, and catalytic enantioselective formal synthesis of CP-293,019, a selective D4 receptor antagonist, was achieved. Preliminary mechanistic studies indicated that both sulfoxides and phosphine sulfides can activate TMSCN as a Lewis base. In addition, the sulfoxides with appropriate stereochemistry might stabilize a highly enantioselective bimetallic complex (a presumed active catalyst) through internal coordination to aluminum. Copyright
Synthesis, SAR and pharmacology of CP-293,019: A potent, selective dopamine D4 receptor antagonist
Sanner, Mark A.,Chappie, Thomas A.,Dunaiskis, Audrey R.,Fliri, Anton F.,Desai, Kishor A.,Zorn, Stevin H.,Jackson, Elisa R.,Johnson, Celeste G.,Morrone, Jean M.,Seymour, Patricia A.,Majchrzak, Mark J.,Faraci, W. Stephen,Collins, Judith L.,Duignan, David B.,Di Prete, Cecilia C.,Lee, Jae S.,Trozzi, Angela
, p. 725 - 730 (2007/10/03)
A series of novel, potent and selective pyrido[1,2-a]pyrazine dopamine D4 receptor antagonists are reported including CP-293,019 (D4 K(i) = 3.4 nM, D2 K(i) > 3,310 nM), which also inhibits apomorphine-induced hyperlocomotion in rats after oral dosing.
