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

α-(4-Tolyl) dopamine, derivatives and analogues; Synthesis and pharmacological screening

V Valenta, J Holubek, E Svátek, A Dlabač…

Index: Valenta; Holubek; Svatek; et al. Collection of Czechoslovak Chemical Communications, 1983 , vol. 48, # 5 p. 1447 - 1464

Full Text: HTML

Citation Number: 8

Abstract

Abstract The ketone XIII, obtained by Friedel-Crafts reaction of toluene with homoveratroyl chloride, was converted by the Leuckart reaction to the formamido derivative IXb which was used as the starting product for the synthesis of amines IIIb-Vb. Reduction of the ketone XIII gave the alcohol XVI which was treated with hydrogen chloride and afforded the chloro compound XVII. Its substitution reactions with 1-methylpiperazine, 1-(2-hydroxyethyl) ...

N-(2-(3,4-dimethoxyphenyl)-1-(4-tolyl)ethyl)acetamide Structure

N-(2-(3,4-dimet...

~%

6,7-dimethoxy-1-methyl-3-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline,hydrochloride Structure

6,7-dimethoxy-1...

2-(3,4-dimethoxyphenyl)-1-(4-methylphenyl)ethanamine,hydrochloride Structure

2-(3,4-dimethox...

~%

6,7-dimethoxy-1-methyl-3-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline,hydrochloride Structure

6,7-dimethoxy-1...

6,7-dimethoxy-1-methyl-3-(4-tolyl)-3,4-dihydroisoquinoline Structure

6,7-dimethoxy-1...

~%

6,7-dimethoxy-1-methyl-3-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline,hydrochloride Structure

6,7-dimethoxy-1...

2-(3,4-dimethoxyphenyl)-N,N-dimethyl-1-(4-methylphenyl)ethanamine,hydrochloride Structure

2-(3,4-dimethox...

~%

[2-benzoyloxy-4-[2-(dimethylamino)-2-(4-methylphenyl)ethyl]phenyl] benzoate,hydrochloride Structure

[2-benzoyloxy-4...

4-(2-(Dimethylamino)-2-(4-methylphenyl)ethyl)-1,2-benzenediol hydrobro mide Structure

4-(2-(Dimethyla...

Benzoyl chloride Structure

Benzoyl chloride

~%

[2-benzoyloxy-4-[2-(dimethylamino)-2-(4-methylphenyl)ethyl]phenyl] benzoate,hydrochloride Structure

[2-benzoyloxy-4...

(3,4-DIMETHOXYPHENYL)ACETYL CHLORIDE Structure

(3,4-DIMETHOXYP...

~%

1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline,hydrochloride Structure

1-[(3,4-dimetho...

2-(3,4-dimethoxyphenyl)-1-(4-methylphenyl)ethanamine,hydrochloride Structure

2-(3,4-dimethox...

~%

1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline,hydrochloride Structure

1-[(3,4-dimetho...

N-(2-(3,4-dimethoxyphenyl)-1-(4-tolyl)ethyl)-3,4-dimethoxyphenylacetamide Structure

N-(2-(3,4-dimet...

~%

1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline,hydrochloride Structure

1-[(3,4-dimetho...

N-(2-(3,4-dimethoxyphenyl)-1-(4-tolyl)ethyl)acetamide Structure

N-(2-(3,4-dimet...

~%

1-methyl-3-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol,hydrobromide Structure

1-methyl-3-(4-m...

2-(3,4-dimethoxyphenyl)-1-(4-methylphenyl)ethanamine,hydrochloride Structure

2-(3,4-dimethox...

~%

1-methyl-3-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol,hydrobromide Structure

1-methyl-3-(4-m...

6,7-dimethoxy-1-methyl-3-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline,hydrochloride Structure

6,7-dimethoxy-1...

~%

1-methyl-3-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol,hydrobromide Structure

1-methyl-3-(4-m...

6,7-dimethoxy-1-methyl-3-(4-tolyl)-3,4-dihydroisoquinoline Structure

6,7-dimethoxy-1...

~%

1-methyl-3-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol,hydrobromide Structure

1-methyl-3-(4-m...

1-[2-(3,4-dimethoxyphenyl)-1-(4-methylphenyl)ethyl]-4-methylpiperazine,dihydrochloride Structure

1-[2-(3,4-dimet...

~72%

4-(2-(4-Methylphenyl)-2-(4-methyl-1-piperazinyl)ethyl)-1,2-benzenediol dihydrobromide hydrate Structure

4-(2-(4-Methylp...

2-(3,4-dimethoxyphenyl)-N,N-dimethyl-1-(4-methylphenyl)ethanamine,hydrochloride Structure

2-(3,4-dimethox...

~68%

4-(2-(Dimethylamino)-2-(4-methylphenyl)ethyl)-1,2-benzenediol hydrobro mide Structure

4-(2-(Dimethyla...

6,7-dimethoxy-3-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline,hydrochloride Structure

6,7-dimethoxy-3...

~95%

6,7-Dihydroxy-3-(4-tolyl)-1,2,3,4-tetrahydroisoquinoline hydrobromide Structure

6,7-Dihydroxy-3...

(3,4-DIMETHOXYPHENYL)ACETYL CHLORIDE Structure

(3,4-DIMETHOXYP...

~%

6,7-Dihydroxy-3-(4-tolyl)-1,2,3,4-tetrahydroisoquinoline hydrobromide Structure

6,7-Dihydroxy-3...

N-[2-(3,4-dimethoxyphenyl)-1-(4-methylphenyl)ethyl]formamide Structure

N-[2-(3,4-dimet...

~%

6,7-Dihydroxy-3-(4-tolyl)-1,2,3,4-tetrahydroisoquinoline hydrobromide Structure

6,7-Dihydroxy-3...

Toluene Structure

~%

6,7-Dihydroxy-3-(4-tolyl)-1,2,3,4-tetrahydroisoquinoline hydrobromide Structure

6,7-Dihydroxy-3...

N/A Structure

~%

6,7-Dihydroxy-3-(4-tolyl)-1,2,3,4-tetrahydroisoquinoline hydrobromide Structure

6,7-Dihydroxy-3...

2-(3,4-dimethoxyphenyl)-N-methyl-1-(4-methylphenyl)ethanamine,hydrochloride Structure

2-(3,4-dimethox...

~99%

4-[2-(methylamino)-2-(4-methylphenyl)ethyl]benzene-1,2-diol,hydrobromide Structure

4-[2-(methylami...

(3,4-DIMETHOXYPHENYL)ACETYL CHLORIDE Structure

(3,4-DIMETHOXYP...

~%

1,2-dimethoxy-4-[2-(4-methylphenyl)ethenyl]benzene Structure

1,2-dimethoxy-4...

Toluene Structure

~%

1,2-dimethoxy-4-[2-(4-methylphenyl)ethenyl]benzene Structure

1,2-dimethoxy-4...

1-(2-(3,4-dimethoxyphenyl)-1-(4-tolyl)ethyl)-4-(2-hydroxyethyl)piperazine Structure

1-(2-(3,4-dimet...

~74%

4-[2-[4-(2-hydroxyethyl)piperazin-1-yl]-2-(4-methylphenyl)ethyl]benzene-1,2-diol,dihydrobromide Structure

4-[2-[4-(2-hydr...

N-(2-Hydroxyethyl)piperazine Structure

N-(2-Hydroxyeth...

~%

4-[2-[4-(2-hydroxyethyl)piperazin-1-yl]-2-(4-methylphenyl)ethyl]benzene-1,2-diol,dihydrobromide Structure

4-[2-[4-(2-hydr...

(3,4-DIMETHOXYPHENYL)ACETYL CHLORIDE Structure

(3,4-DIMETHOXYP...

~%

4-[2-[4-(2-hydroxyethyl)piperazin-1-yl]-2-(4-methylphenyl)ethyl]benzene-1,2-diol,dihydrobromide Structure

4-[2-[4-(2-hydr...

2-(3,4-dimethoxyphenyl)-1-(4-tolyl)ethyl chloride Structure

2-(3,4-dimethox...

~%

4-[2-[4-(2-hydroxyethyl)piperazin-1-yl]-2-(4-methylphenyl)ethyl]benzene-1,2-diol,dihydrobromide Structure

4-[2-[4-(2-hydr...

Toluene Structure

~%

4-[2-[4-(2-hydroxyethyl)piperazin-1-yl]-2-(4-methylphenyl)ethyl]benzene-1,2-diol,dihydrobromide Structure

4-[2-[4-(2-hydr...

(3,4-DIMETHOXYPHENYL)ACETYL CHLORIDE Structure

(3,4-DIMETHOXYP...

~%

6,7-dimethoxy-3-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline,hydrochloride Structure

6,7-dimethoxy-3...

N-[2-(3,4-dimethoxyphenyl)-1-(4-methylphenyl)ethyl]formamide Structure

N-[2-(3,4-dimet...

~%

6,7-dimethoxy-3-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline,hydrochloride Structure

6,7-dimethoxy-3...

Toluene Structure

~%

6,7-dimethoxy-3-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline,hydrochloride Structure

6,7-dimethoxy-3...

N/A Structure

~%

6,7-dimethoxy-3-(4-methylphenyl)-1,2,3,4-tetrahydroisoquinoline,hydrochloride Structure

6,7-dimethoxy-3...