Synthesis and activity of novel 1-or 3-(3-amino-1-phenyl propyl)-1,3-dihydro-2H-benzimidazol-2-ones as selective norepinephrine reuptake inhibitors

• Published in: Bioorganic & medicinal chemistry Vol. 18; no. 23; pp. 6067 - 6070
• Main Authors: PUWEN ZHANG, TEREFENKO, Eugene A, MCCOMAS, Casey C, MAHANEY, Paige E, AN VU, TRYBULSKI, Eugene, KOURY, Elizabeth, JOHNSTON, Grace, BRAY, Jenifer, DEECHER, Darlene
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier 01.12.2008
• Subjects: Benzimidazoles - chemical synthesis; Benzimidazoles - chemistry; Benzimidazoles - pharmacology; Biological and medical sciences; Catecholaminergic system; Combinatorial Chemistry Techniques; Drug Design; Humans; Medical sciences; Molecular Structure; Neuropharmacology; Neurotransmitter Uptake Inhibitors - chemical synthesis; Neurotransmitter Uptake Inhibitors - chemistry; Neurotransmitter Uptake Inhibitors - pharmacology; Neurotransmitters. Neurotransmission. Receptors; Norepinephrine - antagonists & inhibitors; Norepinephrine - metabolism; Pharmacology. Drug treatments; Stereoisomerism; Human; Norepinephrine reuptake inhibitor; Selective reuptake inhibitor; NRI; Nitrogen heterocycle; Dopamine reuptake inhibitor 3-(3-Amino-1-phenyl propyl)-1,3-dihydro- 2H-benzimidazol-2-ones; In vitro; Structure activity relation; Membrane transport; Bicyclic compound; Ureas; Aromatic compound; Norepinephrine; Chemical synthesis; Secondary amine; Carrier protein; Serotonin reuptake inhibitor
• ISSN: 0960-894X; 0968-0896; 1464-3405; 1464-3391
• DOI: 10.1016/j.bmcl.2008.10.026

A series of novel 1- or 3-(3-amino-1-phenyl propyl)-1,3-dihydro-2H-benzimidazol-2-ones as selective norepinephrine reuptake inhibitors was discovered. Several compounds such as 15 and 20 showed good hNET potency. Compounds 15 and 20 also displayed excellent selectivity at hNET that appeared superior to those of reboxetine and atomoxetine (4 and 5).