1379510-08-3Relevant academic research and scientific papers
A general, enantioselective synthesis of N-alkyl terminal aziridines and C2-functionalized azetidines via organocatalysis
Senter, Timothy J.,O'Reilly, Matthew C.,Chong, Katherine M.,Sulikowski, Gary A.,Lindsley, Craig W.
, p. 1276 - 1279 (2015)
A short, high-yielding protocol involving the enantioselective α-chlorination of aldehydes has been developed for the enantioselective synthesis of C2-functionalized aziridines and N-alkyl terminal azetidines from a common intermediate. This methodology allows for the rapid preparation of functionalized aziridines in 50-73% overall yields and 88-94% ee, and azetidines in 22-32% overall yields and 84-92% ee. Moreover, we developed a scalable and cost-effective route to the key organocatalyst (54% overall yield, >95% dr).
Discovery and characterization of ML398, a potent and selective antagonist of the D4 receptor with in vivo activity
Berry, Cynthia B.,Bubser, Michael,Jones, Carrie K.,Hayes, John P.,Wepy, James A.,Locuson, Charles W.,Daniels, J. Scott,Lindsley, Craig W.,Hopkins, Corey R.
, p. 1060 - 1064 (2014)
Herein, we report the structure-activity relationship of a chiral morpholine-based scaffold, which led to the identification of a potent and selective dopamine 4 (D4) receptor antagonist. The 4-chlorobenzyl moiety was identified, and the compound was designated an MLPCN probe molecule, ML398. ML398 is potent against the D4 receptor with IC50 = 130 nM and Ki = 36 nM and shows no activity against the other dopamine receptors tested (>20 μM against D1, D2S, D2L, D3, and D5). Further in vivo studies showed that ML398 reversed cocaine-induced hyperlocomotion at 10 mg/kg.
A general, enantioselective synthesis of 2-substituted thiomorpholines and thiomorpholine 1,1-dioxides
Reed, Carson W.,Lindsley, Craig W.
, (2019/09/10)
In the course of our drug discovery programs, we had need to access chiral, 2-substituted thiomorpholines and their oxidized congeners, thiomorpholine 1,1-dioxides. Here, we disclose a high-yielding, general protocol for the enantioselective synthesis of
A general, enantioselective synthesis of protected morpholines and piperazines
O'Reilly, Matthew C.,Lindsley, Craig W.
, p. 2910 - 2913 (2012/08/14)
A short, high yielding protocol has been developed for the enantioselective and general synthesis of C2-functionalized, benzyl protected morpholines and orthogonally N,N′-protected piperazines from a common intermediate.
