Synthesis, biological activity, and absolute stereochemical assignment of NPS 1392: a potent and stereoselective NMDA receptor antagonist.

Autor: Moe ST; NPS Pharmaceuticals, Inc., Salt Lake City, UT 84108, USA., Shimizu SM, Smith DL, Van Wagenen BC, DelMar EG, Balandrin MF, Chien Y, Raszkiewicz JL, Artman LD, Mueller AL, Lobkovsky E, Clardy J
Jazyk: angličtina
Zdroj: Bioorganic & medicinal chemistry letters [Bioorg Med Chem Lett] 1999 Jul 19; Vol. 9 (14), pp. 1915-20.
DOI: 10.1016/s0960-894x(99)00317-0
Abstrakt: 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.
Databáze: MEDLINE