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

Indoline analogs of idazoxan: potent. alpha. 2-antagonists and. alpha. 1-agonists

GP Fagan, CB Chapleo, AC Lane…

Index: Fagan, Gay P.; Chapleo, Christopher B.; Lane, Anthony C.; Myers, Malcolm; Roach, Alan G.; et al Journal of Medicinal Chemistry, 1988 , vol. 31, # 5 p. 944 - 948

Full Text: HTML

Citation Number: 33

Abstract

The synthesis and a-adrenergic activity of a series of substituted 2-imidazolinylindolines are described. Substitution in the indoline ring generated compounds with a spectrum of adrenoceptor antagonist/agonist profiles that proved sensitive to both the nature and position of the substituent. Many of the derivatives possess greater presynaptic antagonist potency than the corresponding benzodioxan 1, dihydrobenzofuran 2, and indan 3 ...

1,2-Ethanediamine Structure

1,2-Ethanediamine

methyl 1-ethyl-2,3-dihydro-1H-indole-2-carboxylate Structure

methyl 1-ethyl-...

~55%

2-(4,5-dihydro-1H-imidazol-2-yl)-1-ethyl-2,3-dihydroindole Structure

2-(4,5-dihydro-...

Ethyl indole-2-carboxylate Structure

Ethyl indole-2-...

~%

2-(4,5-dihydro-1H-imidazol-2-yl)-1-ethyl-2,3-dihydroindole Structure

2-(4,5-dihydro-...

ethyl 1-ethylindole-2-carboxylate Structure

ethyl 1-ethylin...

~%

2-(4,5-dihydro-1H-imidazol-2-yl)-1-ethyl-2,3-dihydroindole Structure

2-(4,5-dihydro-...

Indole-2-carboxylic acid Structure

Indole-2-carbox...

~%

2-(4,5-dihydro-1H-imidazol-2-yl)-1-ethyl-2,3-dihydroindole Structure

2-(4,5-dihydro-...

2-Chloro-6-nitrotoluene Structure

2-Chloro-6-nitr...

~%

Benzenepropanoic acid,2-chloro-6-nitro-a-oxo- Structure

Benzenepropanoi...

Ethyl indole-2-carboxylate Structure

Ethyl indole-2-...

~%

1-Benzyl-1H-indole-2-carboxylic acid ethyl ester Structure

1-Benzyl-1H-ind...

3-(2-fluoro-6-nitrophenyl)-2-oxopropanoic acid Structure

3-(2-fluoro-6-n...

~62%

4-Fluoro-1H-indole-2-carboxylic acid Structure

4-Fluoro-1H-ind...

Ethyl 2-methylacetoacetate Structure

Ethyl 2-methyla...

4-Chloroaniline Structure

4-Chloroaniline

~%

Propanoic acid,2-[2-(4-chlorophenyl)hydrazinylidene]-, ethyl ester Structure

Propanoic acid,...

4-Chloroaniline Structure

4-Chloroaniline

~%

ETHYL 5-CHLORO-1-METHYL-1H-INDOLE-2-CARBOXYLATE Structure

ETHYL 5-CHLORO-...

Propanoic acid,2-[2-(4-chlorophenyl)hydrazinylidene]-, ethyl ester Structure

Propanoic acid,...

~%

ETHYL 5-CHLORO-1-METHYL-1H-INDOLE-2-CARBOXYLATE Structure

ETHYL 5-CHLORO-...

1H-Indole-2-carboxylicacid, 1-methyl-, ethyl ester Structure

1H-Indole-2-car...

~97%

ethyl 1-methyl-2,3-dihydroindole-2-carboxylate Structure

ethyl 1-methyl-...

Indole-2-carboxylic acid Structure

Indole-2-carbox...

~%

ethyl 1-methyl-2,3-dihydroindole-2-carboxylate Structure

ethyl 1-methyl-...

Ethyl indole-2-carboxylate Structure

Ethyl indole-2-...

~%

ethyl 1-methyl-2,3-dihydroindole-2-carboxylate Structure

ethyl 1-methyl-...

(4-chloro-2-nitro-phenyl)-pyruvic acid Structure

(4-chloro-2-nit...

~%

Ethyl 6-chloro-1H-indole-2-carboxylate Structure

Ethyl 6-chloro-...

6-chloroindole-2-carboxylic acid Structure

6-chloroindole-...

Ethanol Structure

~%

Ethyl 6-chloro-1H-indole-2-carboxylate Structure

Ethyl 6-chloro-...

2-Fluoro-6-nitrotoluene Structure

2-Fluoro-6-nitr...

~%

1H-Indole-2-carboxylic acid, 4-fluoro-, Methyl ester Structure

1H-Indole-2-car...

3-(2-fluoro-6-nitrophenyl)-2-oxopropanoic acid Structure

3-(2-fluoro-6-n...

~%

1H-Indole-2-carboxylic acid, 4-fluoro-, Methyl ester Structure

1H-Indole-2-car...

4-Fluoro-1H-indole-2-carboxylic acid Structure

4-Fluoro-1H-ind...

~%

1H-Indole-2-carboxylic acid, 4-fluoro-, Methyl ester Structure

1H-Indole-2-car...

Indole-2-carboxylic acid Structure

Indole-2-carbox...

~%

ethyl 1-ethylindole-2-carboxylate Structure

ethyl 1-ethylin...

Indole-2-carboxylic acid Structure

Indole-2-carbox...

~%

1H-Indole-2-carboxylicacid, 1-methyl-, ethyl ester Structure

1H-Indole-2-car...

4-Methoxyindole-2-carboxylic acid Structure

4-Methoxyindole...

~%

Methyl 4-methoxy-1-methyl-1H-indole-2-carboxylate Structure

Methyl 4-methox...

2-methyl-3-nitroanisole Structure

2-methyl-3-nitr...

~%

Methyl 4-methoxy-1-methyl-1H-indole-2-carboxylate Structure

Methyl 4-methox...

ethyl 3-(2-methoxy-6-nitrophenyl)-2-oxopropanoate Structure

ethyl 3-(2-meth...

~%

Methyl 4-methoxy-1-methyl-1H-indole-2-carboxylate Structure

Methyl 4-methox...

. alpha. 2-Adrenergic agonists/antagonists: the synthesis an...

[Hlasta; Luttinger; Perrone; Silbernagel; Ward; Haubrich Journal of medicinal chemistry, 1987 , vol. 30, # 9 p. 1555 - 1562]