e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

1-Aryl-3, 4-dihydro-1H-quinolin-2-one derivatives, novel and selective norepinephrine reuptake inhibitors

…, N Dezutter, J Findlay, L Hayhurst, JJ Masters…

Index: Beadle, Christopher D.; Boot, John; Camp, Nicholas P.; Dezutter, Nancy; Findlay, Jeremy; Hayhurst, Lorna; Masters, John J.; Penariol, Roberta; Walter, Magnus W. Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 20 p. 4432 - 4437

Full Text: HTML

Citation Number: 24

Abstract

A novel series of 1-aryl-3, 4-dihydro-1H-quinolin-2-ones have been discovered as potent and selective norepinephrine reuptake inhibitors. Efficient synthetic routes have been developed which allow for the multi-gram preparation of both final targets and advanced intermediates for SAR expansion.

Bromobenzene Structure

~%

3-[2-(methylamino)ethyl]-1-phenyl-3,4-dihydroquinolin-2-one Structure

3-[2-(methylami...

3,4-Dihydroquinolin-2(1H)-one Structure

3,4-Dihydroquin...

~%

3-[2-(methylamino)ethyl]-1-phenyl-3,4-dihydroquinolin-2-one Structure

3-[2-(methylami...

1-phenyl-1,2,3,4-tetrahydroquinolin-2-one Structure

1-phenyl-1,2,3,...

~%

3-[2-(methylamino)ethyl]-1-phenyl-3,4-dihydroquinolin-2-one Structure

3-[2-(methylami...

3-(2-chloroethyl)-1-phenyl-3,4-dihydroquinolin-2-one Structure

3-(2-chloroethy...

methylamine Structure

~%

3-[2-(methylamino)ethyl]-1-phenyl-3,4-dihydroquinolin-2-one Structure

3-[2-(methylami...

3,4-Dihydroquinolin-2(1H)-one Structure

3,4-Dihydroquin...

~%

1-[(4-methoxyphenyl)methyl]-3-methyl-3,4-dihydroquinolin-2-one Structure

1-[(4-methoxyph...

4-Methoxybenzylchloride Structure

4-Methoxybenzyl...

~%

1-[(4-methoxyphenyl)methyl]-3-methyl-3,4-dihydroquinolin-2-one Structure

1-[(4-methoxyph...

1-phenyl-1,2,3,4-tetrahydroquinolin-2-one Structure

1-phenyl-1,2,3,...

~%

3-ethyl-1-phenyl-3,4-dihydroquinolin-2-one Structure

3-ethyl-1-pheny...

Bromobenzene Structure

~%

3-ethyl-1-phenyl-3,4-dihydroquinolin-2-one Structure

3-ethyl-1-pheny...

3,4-Dihydroquinolin-2(1H)-one Structure

3,4-Dihydroquin...

~%

3-ethyl-1-phenyl-3,4-dihydroquinolin-2-one Structure

3-ethyl-1-pheny...

1-phenyl-1,2,3,4-tetrahydroquinolin-2-one Structure

1-phenyl-1,2,3,...

1-Bromo-3-chloropropane Structure

1-Bromo-3-chlor...

~%

3-(3-chloropropyl)-1-phenyl-3,4-dihydroquinolin-2-one Structure

3-(3-chloroprop...

Bromobenzene Structure

~%

3-(3-chloropropyl)-1-phenyl-3,4-dihydroquinolin-2-one Structure

3-(3-chloroprop...

3,4-Dihydroquinolin-2(1H)-one Structure

3,4-Dihydroquin...

~%

3-(3-chloropropyl)-1-phenyl-3,4-dihydroquinolin-2-one Structure

3-(3-chloroprop...

1-phenyl-1,2,3,4-tetrahydroquinolin-2-one Structure

1-phenyl-1,2,3,...

1-Bromo-2-chloroethane Structure

1-Bromo-2-chlor...

~%

3-(2-chloroethyl)-1-phenyl-3,4-dihydroquinolin-2-one Structure

3-(2-chloroethy...

Bromobenzene Structure

~%

3-(2-chloroethyl)-1-phenyl-3,4-dihydroquinolin-2-one Structure

3-(2-chloroethy...

3,4-Dihydroquinolin-2(1H)-one Structure

3,4-Dihydroquin...

~%

3-(2-chloroethyl)-1-phenyl-3,4-dihydroquinolin-2-one Structure

3-(2-chloroethy...

1-phenyl-1,2,3,4-tetrahydroquinolin-2-one Structure

1-phenyl-1,2,3,...

~%

1-phenyl-3-propyl-3,4-dihydroquinolin-2-one Structure

1-phenyl-3-prop...

Bromobenzene Structure

~%

1-phenyl-3-propyl-3,4-dihydroquinolin-2-one Structure

1-phenyl-3-prop...

3,4-Dihydroquinolin-2(1H)-one Structure

3,4-Dihydroquin...

~%

1-phenyl-3-propyl-3,4-dihydroquinolin-2-one Structure

1-phenyl-3-prop...

3-(3-chloropropyl)-1-phenyl-3,4-dihydroquinolin-2-one Structure

3-(3-chloroprop...

methylamine Structure

~%

3-[3-(methylamino)propyl]-1-phenyl-3,4-dihydroquinolin-2-one Structure

3-[3-(methylami...

3-(2-oxo-1-phenyl-1,2,3,4-tetrahydroquinolin-3-yl)propyl methanesulfonate Structure

3-(2-oxo-1-phen...

methylamine Structure

~83%

3-[3-(methylamino)propyl]-1-phenyl-3,4-dihydroquinolin-2-one Structure

3-[3-(methylami...

Bromobenzene Structure

~%

3-[3-(methylamino)propyl]-1-phenyl-3,4-dihydroquinolin-2-one Structure

3-[3-(methylami...

3,4-Dihydroquinolin-2(1H)-one Structure

3,4-Dihydroquin...

~%

3-[3-(methylamino)propyl]-1-phenyl-3,4-dihydroquinolin-2-one Structure

3-[3-(methylami...

1-phenyl-1,2,3,4-tetrahydroquinolin-2-one Structure

1-phenyl-1,2,3,...

~%

3-[3-(methylamino)propyl]-1-phenyl-3,4-dihydroquinolin-2-one Structure

3-[3-(methylami...

3-(3-hydroxypropyl)-1-phenyl-3,4-dihydroquinolin-2(1H)-one Structure

3-(3-hydroxypro...

~%

3-[3-(methylamino)propyl]-1-phenyl-3,4-dihydroquinolin-2-one Structure

3-[3-(methylami...