Title of article :
Synthesis, biological activity, and absolute stereochemical assignment of NPS 1392: a potent and stereoselective NMDA receptor antagonist
Author/Authors :
Scott T. Moe، نويسنده , , Scot M. Shimizu، نويسنده , , Daryl L. Smith، نويسنده , , Bradford C. Van Wagenen، نويسنده , , Eric G. DelMar، نويسنده , , Manuel F. Balandrin، نويسنده , , Yongwei (Eric) Chien، نويسنده , , Joanna L. Raszkiewicz، نويسنده , , Linda D. Artman، نويسنده , , Alan L. Mueller، نويسنده , , Emil Lobkovsky، نويسنده , , Jon Clardy، نويسنده ,
Abstract :
The synthesis, biological activity, and single crystal X-ray structure of NPS 1392, (R)-(−)-3,3-bis(3-fluorophenyl)-2-methylpropan-1-amine (3a), a potent, stereoselective antagonist of the NMDA receptor, are described. The NMDA receptor selectively bound the levo isomer (3a) over its enantiomer (3b), which prompted a rigorous absolute configuration assignment. NPS 1392 has the R configuration based on the single-crystal X-ray diffraction analysis of the hydroiodide salt of NPS 1392. This compound is a potential neuroprotective agent for use in the treatment of ischemic stroke.
