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

Synthesis, structure-activity relationship, and receptor pharmacology of a new series of quinoline derivatives acting as selective, noncompetitive mGlu1 antagonists

…, R Wouters, ASJ Lesage, LV Beijsterveldt…

Index: Mabire, Dominique; Coupa, Sophie; Adelinet, Christophe; Poncelet, Alain; Simonnet, Yvan; Venet, Marc; Wouters, Ria; Lesage, Anne S. J.; Van Beijsterveldt, Ludy; Bischoff, Francois Journal of Medicinal Chemistry, 2005 , vol. 48, # 6 p. 2134 - 2153

Full Text: HTML

Citation Number: 68

Abstract

We describe the discovery and the structure-activity relationship of a new series of quinoline derivatives acting as selective and highly potent noncompetitive mGlu1 antagonists. We first identified cis-10 as a fairly potent mGlu1 antagonist (IC50= 20 nM) in a cell-based signal transduction assay on the rat mGlu1 receptor expressed in CHO-K1 cells, and then we were able to design and synthesize highly potent compounds on both rat and human mGlu1 ...

5-Chlorovaleryl chloride Structure

5-Chlorovaleryl...

~%

8-BROMO-2,3-DIHYDROPYRANO[2,3-B]QUINOLINE Structure

8-BROMO-2,3-DIH...

3-Bromoaniline Structure

~%

8-BROMO-2,3-DIHYDROPYRANO[2,3-B]QUINOLINE Structure

8-BROMO-2,3-DIH...

N/A Structure

~32%

1-(2-chloro-3-ethylquinolin-6-yl)-3-methylbutan-1-one Structure

1-(2-chloro-3-e...

N-(4-bromophenyl)butanamide Structure

N-(4-bromopheny...

~%

1-(2-chloro-3-ethylquinolin-6-yl)-3-methylbutan-1-one Structure

1-(2-chloro-3-e...

4-Bromoaniline Structure

~%

1-(2-chloro-3-ethylquinolin-6-yl)-3-methylbutan-1-one Structure

1-(2-chloro-3-e...

6-Bromo-2-chloro-3-ethylquinoline Structure

6-Bromo-2-chlor...

~%

1-(2-chloro-3-ethylquinolin-6-yl)-3-methylbutan-1-one Structure

1-(2-chloro-3-e...

N-(4-Bromophenyl)-5-chloropentanamide Structure

N-(4-Bromopheny...

~%

7-BROMO-3,4,10,10A-TETRAHYDRO-2H-PYRANO[2,3-B]QUINOLINE Structure

7-BROMO-3,4,10,...

N-(4-Bromophenyl)-5-chloropentanamide Structure

N-(4-Bromopheny...

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~%

6-BROMO-2-CHLORO-3-(3-CHLORO-PROPYL)-QUINOLINE Structure

6-BROMO-2-CHLOR...

N-(4-bromophenyl)butanamide Structure

N-(4-bromopheny...

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~70%

6-Bromo-2-chloro-3-ethylquinoline Structure

6-Bromo-2-chlor...

4-Bromoaniline Structure

~%

6-Bromo-2-chloro-3-ethylquinoline Structure

6-Bromo-2-chlor...

1,4-Benzodioxan-2-carboxylic acid Structure

1,4-Benzodioxan...

N,O-Dimethylhydroxylamine hydrochloride Structure

N,O-Dimethylhyd...

~92%

N-METHOXY-N-METHYL-2,3-DIHYDROBENZO[B][1,4]DIOXINE-2-CARBOXAMIDE Structure

N-METHOXY-N-MET...

Butyryl chloride Structure

Butyryl chloride

4-Bromoaniline Structure

~99%

N-(4-bromophenyl)butanamide Structure

N-(4-bromopheny...

(E)-3-chloro-2-ethylbut-2-enal Structure

(E)-3-chloro-2-...

4-Bromoaniline Structure

~%

6-Bromo-3-ethyl-2-methylquinoline Structure

6-Bromo-3-ethyl...

N,4-dimethoxy-N-cis/trans-methylcyclohexanecarboxamide Structure

N,4-dimethoxy-N...

6-Bromo-2-chloro-3-ethylquinoline Structure

6-Bromo-2-chlor...

~28%

(2-chloro-3-ethylquinolin-6-yl)((1r,4r)-4-methoxycyclohexyl)methanone Structure

(2-chloro-3-eth...

(2-chloro-3-ethylquinolin-6-yl)-(4-methoxycyclohexyl)methanone Structure

(2-chloro-3-eth...

4-Bromoaniline Structure

~%

(2-chloro-3-ethylquinolin-6-yl)-(4-methoxycyclohexyl)methanone Structure

(2-chloro-3-eth...

(4-methoxycyclohexyl)acetic acid (en) Structure

(4-methoxycyclo...

N,O-Dimethylhydroxylamine hydrochloride Structure

N,O-Dimethylhyd...

~%

N-Methoxy-2-(4-methoxycyclohexyl)-N-methylacetamide Structure

N-Methoxy-2-(4-...