Synthesis and evaluation of conformationally restricted N-[2-(3,4-dichlorophenyl)ethyl]-N-methyl-2-(1-pyrrolidinyl)ethylamines at σ receptors. 2. Piperazines, bicyclic amines, bridged bicyclic amines, and miscellaneous compounds was written by de Costa, Brian R.;He, Xiaoshu;Linders, Joannes T. M.;Dominguez, Celia;Gu, Zi Qiang;Williams, Wanda;Bowen, Wayne. And the article was included in Journal of Medicinal Chemistry in 1993.Computed Properties of C7H16N2 This article mentions the following:
As a continuation of an earlier study (J. Med. Chem. 1992, 35, 4334-4343) the σ-receptor ligand was conformationally restricted in 2-(1-pyrrolidinyl)-N-[2-(3,4-dichlorophenyl)ethyl]-N-methylethylamine (I) by incorporating it into homologous piperazines and homopiperazines, diazabicyclononanes and decanes, bridgehead bicyclooctanes and nonanes as well as other miscellaneous compounds σ-Receptor binding affinities were obtained using [3H](+)-pentazocine in guinea pig brain membranes. Probably the N lone pair orientation found in the piperazines affords the strongest binding interaction. Other N lone pair orientations or compounds representing unlikely staggered conformations of I [as in 4-[2-(3,4-dichlorophenyl)ethyl]-1,4-diazabicyclo[3.2.2]nonane] show very weak σ interaction. Comparison of the binding data of different N-substituted homologs of I with those of the 1-[2-(3,4-dichlorophenyl)ethyl]-4-alkylpiperazines suggests that the 2 N atoms of I are working in opposition to one another in terms of their sensitivity to steric bulk. The high binding affinity of 1,4-diazabicyclo[4.3.0]nonanes suggests that these may approx. the Me and pyrrolidine ring conformations found in I when it is bound to the σ receptor. Binding data suggest that the conformation of I favors strong binding interaction at σ-receptors. σ-Receptor Ki‘s was 0.55 nM for 1-[2-(3,4-dichlorophenyl)ethyl]-4-n-butylpiperazine. Overall comparison of the results indicate that I is subject to considerable conformational freedom and suggests that the σ receptor is not subject to rigid stereochem. restraints with I. These results corroborate an earlier study where I was restrained using simple monocyclic heterocycles. In the experiment, the researchers used many compounds, for example, 1-Propylpiperazine (cas: 21867-64-1Computed Properties of C7H16N2).
1-Propylpiperazine (cas: 21867-64-1) belongs to piperazine derivatives. Piperazine causes primary dermal irritation and skin burns at high concentrations. Piperazine also causes eye irritation in humans. Piperazine is an anthelminthic especially useful in the treatment of partial intestinal obstruction caused by Ascaris worms, which is a condition primarily seen in children. Piperazine hydrate and piperazine citrate are the main anthelminthic piperazines.Computed Properties of C7H16N2
Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics