649761-78-4Relevant articles and documents
Bioisosteric replacement and related analogs in the design, synthesis and evaluation of ligands for muscarinic acetylcholine receptors
Bhandare, Richie R.,Canney, Daniel J.
, p. 361 - 375 (2014/05/20)
Previous structure-activity relationship studies involving a series of lactone-based muscarinic ligands identified a lead compound containing a diphenylmethylpiperazine moiety (4; IC50 = 340 nM). The purpose of the present work is to investigate 1,3-benzodioxoles, 4,4-diethyl substituted tetrahydrofurans, 5-substituted oxazolidinones and chromones as bioisosteric replacements for the lactone ring in a novel series of muscarinic ligands. The approach provided compounds with improved % inhibition values and identified a non-selective muscarinic ligand with an IC50 value of 280 nM. The structure-activity relationship for this new series will be discussed. Selected compounds were evaluated in preliminary assays for subtype selectivity and were found to be non-selective.
Convenient synthesis of oxazolidinones by the use of halomethyloxirane, primary amine, and carbonate salt
Osa, Yumiko,Hikima, Yuka,Sato, Yoko,Takino, Kouichi,Ida, Yoshihiro,Hirono, Shuichi,Nagase, Hiroshi
, p. 5737 - 5740 (2007/10/03)
Primary amines reacted with carbonate salts (Na2CO3, K2CO3, Cs2CO3, and Ag 2CO3) and halomethyloxiranes in the presence of a base such as DBU or TEA to give oxazolidinones in high yields. The use of K 2CO3 among these carbonate gave the best yield in this synthesis. A reaction mechanism was proposed that the oxazolidinone was obtained from an oxazinanone intermediate via a bicyclo[2.2.1] intermediate. The present reaction can be widely applied to convenient synthesis of useful N-substituted oxazolidinones and chiral oxazolidinones.
