1239983-29-9Relevant academic research and scientific papers
Design, synthesis, and structure-affinity relationships of regioisomeric N-benzyl alkyl ether piperazine derivatives as σ-1 receptor ligands
Moussa, Iman A.,Banister, Samuel D.,Beinat, Corinne,Giboureau, Nicolas,Reynolds, Aaron J.,Kassiou, Michael
experimental part, p. 6228 - 6239 (2010/11/02)
A series of N-(benzofuran-2-ylmethyl)-N′-benzylpiperazines bearing alkyl or fluoroalkyl aryl ethers were synthesized and evaluated at various central nervous system receptors. Examination of in vitro σ1 {[3H](+)-pentazocine} and σ2 ([3H]DTG) receptor binding profiles of piperazines 11-13 and 25-36 revealed several highly potent and σ1 selective ligands, notably, N-(benzofuran-2- ylmethyl)-N′-(4′-methoxybenzyl)piperazine (13, Ki = 2.7 nM, σ2/σ1 = 38) and N-(benzofuran-2-ylmethyl)- N′-(4′-(2″-fluoroethoxy)benzyl)piperazine (30, Ki = 2.6 nM, σ2/σ1 = 187). Structural features for optimal σ1 receptor affinity and selectivity over the σ2 receptor were identified. On the basis of its favorable log D value, 13 was selected as a candidate for the development of a σ1 receptor positron emission tomography radiotracer. [ 11C]13 showed high uptake in the brain and other σ receptor-rich organs of a Papio hamadryas baboon. The in vivo evaluation of [11C]13 indicates that this radiotracer is a suitable candidate for imaging the σ1 receptor in neurodegenerative processes.
