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

Structure-activity relationships of arylimidazopyridine cardiotonics: discovery and inotropic activity of 2-[2-methoxy-4-(methylsulfinyl) phenyl]-1H-imidazo [4, 5-c] …

DW Robertson, EE Beedle, JH Krushinski…

Index: Robertson; Beedle; Krushinski; Pollock; Wilson; Wyss; Hayes Journal of Medicinal Chemistry, 1985 , vol. 28, # 6 p. 717 - 727

Full Text: HTML

Citation Number: 63

Abstract

Method A. To a stirred suspension of 1.5-2 equiv of sodium hydride (50% dispersion in oil) in 1, 4-dioxane was added dropwise a solution of 1.5-2 equiv of the substituted aniline and the mixture was heated at 100" C for 2 h. A solution of 1 equiv of compound 4 in 1, 4-dioxane was added to the above-stirred mixture at room temperature and then heated at 100" C for 2 h. The reaction mixture was poured into ice-water and extracted with ether. The ether layer ...

3,4-Diaminopyridine Structure

3,4-Diaminopyridine

4-(methylthio)-2-n-propoxybenzoic acid Structure

4-(methylthio)-...

~54%

2-(4-methylsulfanyl-2-propoxyphenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(4-methylsulf...

3-(Methylthio)phenol Structure

3-(Methylthio)phenol

~%

2-(4-methylsulfanyl-2-propoxyphenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(4-methylsulf...

Benzoic acid, 2-hydroxy-4-(methylthio)- Structure

Benzoic acid, 2...

~%

2-(4-methylsulfanyl-2-propoxyphenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(4-methylsulf...

methyl 2-hydroxy-4-methylsulfanylbenzoate Structure

methyl 2-hydrox...

~%

2-(4-methylsulfanyl-2-propoxyphenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(4-methylsulf...

4-(methylthio)-2-n-propoxybenzoic acid methyl ester Structure

4-(methylthio)-...

~%

2-(4-methylsulfanyl-2-propoxyphenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(4-methylsulf...

3,4-Diaminopyridine Structure

3,4-Diaminopyridine

2,4-Dichlorobenzoic acid Structure

2,4-Dichloroben...

~79%

2-(2,4-dichlorophenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(2,4-dichloro...

3,4-Diaminopyridine Structure

3,4-Diaminopyridine

4-Methylbenzoic acid Structure

4-Methylbenzoic acid

~%

2-(4-methylphenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(4-methylphen...

2-Methylbenzoic acid Structure

2-Methylbenzoic acid

3,4-Diaminopyridine Structure

3,4-Diaminopyridine

~%

2-(2-methylphenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(2-methylphen...

2-METHOXY-4-MERCAPTOBENZOIC ACID Structure

2-METHOXY-4-MER...

Dimethyl sulfate Structure

Dimethyl sulfate

~%

methyl 2-methoxy-4-methylsulfanylbenzoate Structure

methyl 2-methox...

3,4-Diaminopyridine Structure

3,4-Diaminopyridine

2,4-Dimethylbenzoic acid Structure

2,4-Dimethylben...

~%

2-(2,4-dimethylphenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(2,4-dimethyl...

3,4-Diaminopyridine Structure

3,4-Diaminopyridine

4-methoxy-2-(2-methoxyethoxy)benzoic acid Structure

4-methoxy-2-(2-...

~27%

2-[4-methoxy-2-(2-methoxyethoxy)phenyl]-3H-imidazo[4,5-c]pyridine Structure

2-[4-methoxy-2-...

2-(4-methylsulfanyl-2-propoxyphenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(4-methylsulf...

~68%

2-(4-methylsulfinyl-2-propoxyphenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(4-methylsulf...

3,4-Diaminopyridine Structure

3,4-Diaminopyridine

~%

2-(4-methylsulfinyl-2-propoxyphenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(4-methylsulf...

3-(Methylthio)phenol Structure

3-(Methylthio)phenol

~%

2-(4-methylsulfinyl-2-propoxyphenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(4-methylsulf...

Benzoic acid, 2-hydroxy-4-(methylthio)- Structure

Benzoic acid, 2...

~%

2-(4-methylsulfinyl-2-propoxyphenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(4-methylsulf...

methyl 2-hydroxy-4-methylsulfanylbenzoate Structure

methyl 2-hydrox...

~%

2-(4-methylsulfinyl-2-propoxyphenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(4-methylsulf...

4-(methylthio)-2-n-propoxybenzoic acid methyl ester Structure

4-(methylthio)-...

~%

2-(4-methylsulfinyl-2-propoxyphenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(4-methylsulf...

4-(methylthio)-2-n-propoxybenzoic acid Structure

4-(methylthio)-...

~%

2-(4-methylsulfinyl-2-propoxyphenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(4-methylsulf...

3,4-Diaminopyridine Structure

3,4-Diaminopyridine

3,5-Dichlorobenzoic acid Structure

3,5-Dichloroben...

~%

2-(3,5-dichlorophenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(3,5-dichloro...

2-(4-methoxy-2-methylsulfanylphenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(4-methoxy-2-...

~%

2-(4-methoxy-2-methylsulfinylphenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(4-methoxy-2-...

3,4-Diaminopyridine Structure

3,4-Diaminopyridine

3-Fluorobenzoic acid Structure

3-Fluorobenzoic acid

~%

2-(3-fluorophenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(3-fluorophen...

3,4-Diaminopyridine Structure

3,4-Diaminopyridine

3-Methylbenzoic acid Structure

3-Methylbenzoic acid

~54%

2-(3-methylphenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(3-methylphen...

3,4-Diaminopyridine Structure

3,4-Diaminopyridine

4-Methylsulfonyl benzoic acid Structure

4-Methylsulfony...

~%

2-(4-methylsulfonylphenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(4-methylsulf...

3,4-Diaminopyridine Structure

3,4-Diaminopyridine

4-Fluorobenzoic acid Structure

4-Fluorobenzoic acid

~%

2-(4-fluorophenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(4-fluorophen...

3,4-Diaminopyridine Structure

3,4-Diaminopyridine

Paraxylic Acid Structure

~%

2-(3,4-dimethylphenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(3,4-dimethyl...

3,4-Diaminopyridine Structure

3,4-Diaminopyridine

2-Ethoxy-4-methoxybenzoic acid Structure

2-Ethoxy-4-meth...

~64%

2-(2-ethoxy-4-methoxyphenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(2-ethoxy-4-m...

Benzoic acid, 2-hydroxy-4-(methylthio)- Structure

Benzoic acid, 2...

Dimethyl sulfate Structure

Dimethyl sulfate

~90%

methyl 2-hydroxy-4-methylsulfanylbenzoate Structure

methyl 2-hydrox...

3-(Methylthio)phenol Structure

3-(Methylthio)phenol

~%

methyl 2-hydroxy-4-methylsulfanylbenzoate Structure

methyl 2-hydrox...

Carbon dioxide Structure

3-(Methylthio)phenol Structure

3-(Methylthio)phenol

~70%

Benzoic acid, 2-hydroxy-4-(methylthio)- Structure

Benzoic acid, 2...

methyl 2-methoxy-4-methylsulfanylbenzoate Structure

methyl 2-methox...

~%

2-Methoxy-4-(methylsulfanyl)benzoic acid Structure

2-Methoxy-4-(me...

3,4-Diaminopyridine Structure

3,4-Diaminopyridine

2-Butoxy-4-methoxybenzoic acid Structure

2-Butoxy-4-meth...

~52%

2-(2-butoxy-4-methoxyphenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(2-butoxy-4-m...

3,4-Diaminopyridine Structure

3,4-Diaminopyridine

3,5-Dimethoxybenzoic acid Structure

3,5-Dimethoxybe...

~47%

2-(3,5-dimethoxyphenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(3,5-dimethox...

3,4-Diaminopyridine Structure

3,4-Diaminopyridine

2,4,6-Trimethoxybenzoic acid Structure

2,4,6-Trimethox...

~7%

2-(2,4,6-trimethoxyphenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(2,4,6-trimet...

3,4-Diaminopyridine Structure

3,4-Diaminopyridine

N/A Structure

~77%

2-[4-methoxy-2-(3-methoxypropoxy)phenyl]-3H-imidazo[4,5-c]pyridine Structure

2-[4-methoxy-2-...

3,4-Diaminopyridine Structure

3,4-Diaminopyridine

2-ethoxy-4-methylsulfanylbenzoic acid Structure

2-ethoxy-4-meth...

~77%

2-(2-ethoxy-4-methylsulfanylphenyl)-3H-imidazo[4,5-c]pyridine Structure

2-(2-ethoxy-4-m...