38944-14-8Relevant articles and documents
Design, synthesis and biological evaluation of N-hydroxy-aminobenzyloxyarylamide analogues as novel selective κ opioid receptor antagonists
He, Guangchao,Peng, Kewen,Song, Qiao,Wang, Junwei,Xu, Anhua,Xu, Yungen,Zhu, Qihua
, (2020/05/19)
Aminobenzyloxyarylamide derivatives 1a-i and 2a-t were designed and synthesized as novel selective κ opioid receptor (KOR) antagonists. The benzoyl amide moiety of LY2456302 was changed into N-hydroxybenzamide and benzisoxazole-3(2H)-one to investigate whether it could increase the binding affinity or selectivity for KOR. All target compounds were evaluated in radioligand binding assays for opioid receptor binding affinity. These efforts led to the identification of compound 1c (κ Ki = 179.9 nM), which exhibited high affinity for KOR. Moreover, the selectivity of KOR over MOR and DOR increased nearly 2-fold and 7-fold, respectively, compared with (±)LY2456302.
Stereocomplementary Synthesis of Pharmaceutically Relevant Chiral 2-Aryl-Substituted Pyrrolidines Using Imine Reductases
Chen, Fei-Fei,Chen, Qi,Li, Bo-Bo,Xu, Jian-He,Zhang, Yu-Hui,Zheng, Gao-Wei,Zhou, Xin-Yi
supporting information, p. 3367 - 3372 (2020/04/21)
Exploring a collection of naturally occurring imine reductases (IREDs) identified two stereocomplementary IREDs with reducing activity toward sterically hindered 2-aryl-substituted pyrrolines. Using (R)-selective ScIR and (S)-selective SvIR, various chiral 2-aryl-substituted pyrrolidines with excellent enantioselectivity (>99% ee) were stereocomplementarily synthesized in good yield (60-80%), demonstrating the feasibility of IREDs for generating pharmaceutically relevant chiral 2-aryl-substituted pyrrolidine intermediates.
Hammett correlation of nornicotine analogues in the aqueous aldol reaction: Implications for green organocatalysis
Rogers, Claude J.,Dickerson, Tobin J.,Brogan, Andrew P.,Janda, Kim D.
, p. 3705 - 3708 (2007/10/03)
(Chemical Equation Presented) A series of meta- and para-substituted 2-arylpyrrolidines were synthesized and examined for their ability to catalyze an aqueous aldol reaction under buffered conditions. Kinetic analysis of arylpyrrolidine-catalyzed reactions displayed a linear Hammett correlation with ρ = 1.14 (R2 = 0.996), indicating that the reaction is accelerated by electron-withdrawing aryl rings. These results show promise for the development of a synthetically viable aqueous organocatalyst.
