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

. beta. 1-Selective adrenoceptor antagonists. 3. 4-Azolyl linked phenoxypropanolamines

…, LC Blaber, DT Burden, RA Melarange

Index: Machin, Peter J.; Hurst, David N.; Bradshaw, Rachel M.; Blaber, Leslie C.; Burden, David T.; Melarange, Rosemary A. Journal of Medicinal Chemistry, 1984 , vol. 27, # 4 p. 503 - 509

Full Text: HTML

Citation Number: 22

Abstract

A series of 4-substituted phenoxypropanolamines has been prepared and examined for P- adrenoceptor activity. The 4-substituenta, di-and triazole ring systems connected to the phenoxy ring by different length chains, were chosen as a means of introducing cardioselectivity. This has been achieved, especially in the l-[4-[(4-chloropyrazol-lyl) methoxy] phenoxy]-3-(isopropylamino)-2-propanol (ll), the 4-[(2H-1, 2, 3-triazol-2-yl) ...

1-[2-(4-phenylmethoxyphenoxy)ethyl]-1,2,4-triazole Structure

1-[2-(4-phenylm...

~84%

4-[2-(1,2,4-triazol-1-yl)ethoxy]phenol Structure

4-[2-(1,2,4-tri...

1-(BENZYLOXY)-4-(2-BROMOETHOXY)BENZENE Structure

1-(BENZYLOXY)-4...

~%

4-[2-(1,2,4-triazol-1-yl)ethoxy]phenol Structure

4-[2-(1,2,4-tri...

4-Mercaptophenol Structure

4-Mercaptophenol

1-CHLOROMETHYL-1H-PYRAZOLE Structure

1-CHLOROMETHYL-...

~83%

4-(pyrazol-1-ylmethylsulfanyl)phenol Structure

4-(pyrazol-1-yl...

Pyrazole Structure

1-(BENZYLOXY)-4-(2-BROMOETHOXY)BENZENE Structure

1-(BENZYLOXY)-4...

~%

1-[2-(4-phenylmethoxyphenoxy)ethyl]pyrazole Structure

1-[2-(4-phenylm...

1-[3-(4-phenylmethoxyphenoxy)propyl]pyrazole Structure

1-[3-(4-phenylm...

~61%

4-(3-pyrazol-1-ylpropoxy)phenol Structure

4-(3-pyrazol-1-...

1-(BENZYLOXY)-4-(3-BROMOPROPOXY)BENZENE Structure

1-(BENZYLOXY)-4...

~%

4-(3-pyrazol-1-ylpropoxy)phenol Structure

4-(3-pyrazol-1-...

1-[3-(4-phenylmethoxyphenoxy)propyl]-1,2,4-triazole Structure

1-[3-(4-phenylm...

~62%

4-[3-(1,2,4-triazol-1-yl)propoxy]phenol Structure

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

1-(BENZYLOXY)-4-(3-BROMOPROPOXY)BENZENE Structure

1-(BENZYLOXY)-4...

~%

4-[3-(1,2,4-triazol-1-yl)propoxy]phenol Structure

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

4-phenyl-1-[2-(4-phenylmethoxyphenoxy)ethyl]pyrazole Structure

4-phenyl-1-[2-(...

~83%

4-[2-(4-phenylpyrazol-1-yl)ethoxy]phenol Structure

4-[2-(4-phenylp...

4-Phenyl-1H-pyrazole Structure

4-Phenyl-1H-pyrazole

~%

4-[2-(4-phenylpyrazol-1-yl)ethoxy]phenol Structure

4-[2-(4-phenylp...

1-(BENZYLOXY)-4-(2-BROMOETHOXY)BENZENE Structure

1-(BENZYLOXY)-4...

~%

4-[2-(4-phenylpyrazol-1-yl)ethoxy]phenol Structure

4-[2-(4-phenylp...

1H-Indazole Structure

1-(BENZYLOXY)-4-(2-BROMOETHOXY)BENZENE Structure

1-(BENZYLOXY)-4...

~%

2-[2-(4-phenylmethoxyphenoxy)ethyl]indazole Structure

2-[2-(4-phenylm...

1-[2-(4-phenylmethoxyphenoxy)ethyl]indazole Structure

1-[2-(4-phenylm...

triazole Structure

1-(BENZYLOXY)-4-(2-BROMOETHOXY)BENZENE Structure

1-(BENZYLOXY)-4...

~%

2-[2-(4-phenylmethoxyphenoxy)ethyl]triazole Structure

2-[2-(4-phenylm...

1-[2-(4-phenylmethoxyphenoxy)ethyl]triazole Structure

1-[2-(4-phenylm...

1,2,4-Triazole Structure

methanesulfonic acid,2-(4-phenylmethoxyphenyl)ethanol Structure

methanesulfonic...

~%

1-[2-(4-phenylmethoxyphenyl)ethyl]-1,2,4-triazole Structure

1-[2-(4-phenylm...

Pyrazole Structure

methanesulfonic acid,2-(4-phenylmethoxyphenyl)ethanol Structure

methanesulfonic...

~%

1-[2-(4-phenylmethoxyphenyl)ethyl]pyrazole Structure

1-[2-(4-phenylm...

Imidazole Structure

methanesulfonic acid,2-(4-phenylmethoxyphenyl)ethanol Structure

methanesulfonic...

~%

1-[2-(4-phenylmethoxyphenyl)ethyl]imidazole Structure

1-[2-(4-phenylm...

4-Benzyloxyphenol Structure

4-Benzyloxyphenol

1-(chloromethyl)-1,2,3-triazole hydrochloride Structure

1-(chloromethyl...

~%

2-[(4-phenylmethoxyphenoxy)methyl]triazole Structure

2-[(4-phenylmet...

1-[(4-phenylmethoxyphenoxy)methyl]triazole Structure

1-[(4-phenylmet...

4-chloro-1-[2-(4-phenylmethoxyphenoxy)ethyl]pyrazole Structure

4-chloro-1-[2-(...

~53%

4-[2-(4-chloropyrazol-1-yl)ethoxy]phenol Structure

4-[2-(4-chlorop...

1-(BENZYLOXY)-4-(2-BROMOETHOXY)BENZENE Structure

1-(BENZYLOXY)-4...

~%

4-[2-(4-chloropyrazol-1-yl)ethoxy]phenol Structure

4-[2-(4-chlorop...

1-[2-(4-phenylmethoxyphenyl)ethyl]imidazole Structure

1-[2-(4-phenylm...

~75%

4-(2-imidazol-1-ylethyl)phenol Structure

4-(2-imidazol-1...

methanesulfonic acid,2-(4-phenylmethoxyphenyl)ethanol Structure

methanesulfonic...

~%

4-(2-imidazol-1-ylethyl)phenol Structure

4-(2-imidazol-1...

1-[2-(4-phenylmethoxyphenyl)ethyl]pyrazole Structure

1-[2-(4-phenylm...

~68%

4-(2-pyrazol-1-ylethyl)phenol Structure

4-(2-pyrazol-1-...

methanesulfonic acid,2-(4-phenylmethoxyphenyl)ethanol Structure

methanesulfonic...

~%

4-(2-pyrazol-1-ylethyl)phenol Structure

4-(2-pyrazol-1-...

4-Phenyl-1H-pyrazole Structure

4-Phenyl-1H-pyrazole

1-(BENZYLOXY)-4-(2-BROMOETHOXY)BENZENE Structure

1-(BENZYLOXY)-4...

~%

4-phenyl-1-[2-(4-phenylmethoxyphenoxy)ethyl]pyrazole Structure

4-phenyl-1-[2-(...

Imidazole Structure

1-(BENZYLOXY)-4-(2-BROMOETHOXY)BENZENE Structure

1-(BENZYLOXY)-4...

~%

1-[2-(4-phenylmethoxyphenoxy)ethyl]imidazole Structure

1-[2-(4-phenylm...

Benzimidazole Structure

1-(BENZYLOXY)-4-(2-BROMOETHOXY)BENZENE Structure

1-(BENZYLOXY)-4...

~%

1-[2-(4-phenylmethoxyphenoxy)ethyl]benzimidazole Structure

1-[2-(4-phenylm...

1,2,4-Triazole Structure

1-(BENZYLOXY)-4-(2-BROMOETHOXY)BENZENE Structure

1-(BENZYLOXY)-4...

~%

1-[2-(4-phenylmethoxyphenoxy)ethyl]-1,2,4-triazole Structure

1-[2-(4-phenylm...

4-Benzyloxyphenol Structure

4-Benzyloxyphenol

1-(chloromethyl)-1,2,3-triazole hydrochloride Structure

1-(chloromethyl...

~%

2-[(4-phenylmethoxyphenoxy)methyl]triazole Structure

2-[(4-phenylmet...

1-[(4-phenylmethoxyphenoxy)methyl]triazole Structure

1-[(4-phenylmet...

1-[2-(4-phenylmethoxyphenoxy)ethyl]pyrazole Structure

1-[2-(4-phenylm...

~55%

4-(2-pyrazol-1-ylethoxy)phenol Structure

4-(2-pyrazol-1-...

1-(BENZYLOXY)-4-(2-BROMOETHOXY)BENZENE Structure

1-(BENZYLOXY)-4...

~%

4-(2-pyrazol-1-ylethoxy)phenol Structure

4-(2-pyrazol-1-...

1-[2-(4-phenylmethoxyphenoxy)ethyl]imidazole Structure

1-[2-(4-phenylm...

~96%

4-(2-imidazol-1-ylethoxy)phenol Structure

4-(2-imidazol-1...

1-(BENZYLOXY)-4-(2-BROMOETHOXY)BENZENE Structure

1-(BENZYLOXY)-4...

~%

4-(2-imidazol-1-ylethoxy)phenol Structure

4-(2-imidazol-1...

1-[2-(4-phenylmethoxyphenyl)ethyl]-1,2,4-triazole Structure

1-[2-(4-phenylm...

~82%

4-[2-(1,2,4-triazol-1-yl)ethyl]phenol Structure

4-[2-(1,2,4-tri...

methanesulfonic acid,2-(4-phenylmethoxyphenyl)ethanol Structure

methanesulfonic...

~%

4-[2-(1,2,4-triazol-1-yl)ethyl]phenol Structure

4-[2-(1,2,4-tri...

4-Chloro-1H-pyrazole Structure

4-Chloro-1H-pyrazole

1-(BENZYLOXY)-4-(2-BROMOETHOXY)BENZENE Structure

1-(BENZYLOXY)-4...

~%

4-chloro-1-[2-(4-phenylmethoxyphenoxy)ethyl]pyrazole Structure

4-chloro-1-[2-(...

1H-Indazole Structure

1-(BENZYLOXY)-4-(2-BROMOETHOXY)BENZENE Structure

1-(BENZYLOXY)-4...

~%

2-[2-(4-phenylmethoxyphenoxy)ethyl]indazole Structure

2-[2-(4-phenylm...

1-[2-(4-phenylmethoxyphenoxy)ethyl]indazole Structure

1-[2-(4-phenylm...

triazole Structure

1-(BENZYLOXY)-4-(2-BROMOETHOXY)BENZENE Structure

1-(BENZYLOXY)-4...

~%

2-[2-(4-phenylmethoxyphenoxy)ethyl]triazole Structure

2-[2-(4-phenylm...

1-[2-(4-phenylmethoxyphenoxy)ethyl]triazole Structure

1-[2-(4-phenylm...

Pyrazole Structure

3-(dimethylamino)-1-(4-phenylmethoxyphenyl)propan-1-one Structure

3-(dimethylamin...

~68%

1-(4-phenylmethoxyphenyl)-3-pyrazol-1-ylpropan-1-one Structure

1-(4-phenylmeth...

4-Chloro-1H-pyrazole Structure

4-Chloro-1H-pyrazole

Formaldehyde Structure

~74%

(4-chloropyrazol-1-yl)methanol Structure

(4-chloropyrazo...

Pyrazole Structure

4-Hydroxybenzyl alcohol Structure

4-Hydroxybenzyl...

~46%

1-(4-hydroxybenzyl)pyrazole Structure

1-(4-hydroxyben...

(4-chloropyrazol-1-yl)methanol Structure

(4-chloropyrazo...

~%

1H-Pyrazole, 4-chloro-1-(chloromethyl)- Structure

1H-Pyrazole, 4-...

2-(1-Pyrazolyl)ethanol Structure

2-(1-Pyrazolyl)...

~%

4-(2-pyrazol-1-ylethylsulfanyl)phenol Structure

4-(2-pyrazol-1-...

1-[2-(4-phenylmethoxyphenoxy)ethyl]indazole Structure

1-[2-(4-phenylm...

~58%

4-(2-indazol-1-ylethoxy)phenol Structure

4-(2-indazol-1-...

1H-Indazole Structure

~%

4-(2-indazol-1-ylethoxy)phenol Structure

4-(2-indazol-1-...

1-(BENZYLOXY)-4-(2-BROMOETHOXY)BENZENE Structure

1-(BENZYLOXY)-4...

~%

4-(2-indazol-1-ylethoxy)phenol Structure

4-(2-indazol-1-...

2-[2-(4-phenylmethoxyphenoxy)ethyl]triazole Structure

2-[2-(4-phenylm...

~82%

4-[2-(triazol-2-yl)ethoxy]phenol Structure

4-[2-(triazol-2...

1-(BENZYLOXY)-4-(2-BROMOETHOXY)BENZENE Structure

1-(BENZYLOXY)-4...

~%

4-[2-(triazol-2-yl)ethoxy]phenol Structure

4-[2-(triazol-2...

1,2,4-Triazole Structure

1-(BENZYLOXY)-4-(3-BROMOPROPOXY)BENZENE Structure

1-(BENZYLOXY)-4...

~%

1-[3-(4-phenylmethoxyphenoxy)propyl]-1,2,4-triazole Structure

1-[3-(4-phenylm...

Pyrazole Structure

1-(BENZYLOXY)-4-(3-BROMOPROPOXY)BENZENE Structure

1-(BENZYLOXY)-4...

~%

1-[3-(4-phenylmethoxyphenoxy)propyl]pyrazole Structure

1-[3-(4-phenylm...

2-[(4-phenylmethoxyphenoxy)methyl]triazole Structure

2-[(4-phenylmet...

~59%

4-(triazol-2-ylmethoxy)phenol Structure

4-(triazol-2-yl...

4-Benzyloxyphenol Structure

4-Benzyloxyphenol

~%

4-(triazol-2-ylmethoxy)phenol Structure

4-(triazol-2-yl...

4-Benzyloxyphenol Structure

4-Benzyloxyphenol

~%

4-(triazol-1-ylmethoxy)phenol Structure

4-(triazol-1-yl...

1-[2-(4-phenylmethoxyphenoxy)ethyl]benzimidazole Structure

1-[2-(4-phenylm...

~80%

4-[2-(benzimidazol-1-yl)ethoxy]phenol Structure

4-[2-(benzimida...

Benzimidazole Structure

~%

4-[2-(benzimidazol-1-yl)ethoxy]phenol Structure

4-[2-(benzimida...

1-(BENZYLOXY)-4-(2-BROMOETHOXY)BENZENE Structure

1-(BENZYLOXY)-4...

~%

4-[2-(benzimidazol-1-yl)ethoxy]phenol Structure

4-[2-(benzimida...

1-[(4-phenylmethoxyphenoxy)methyl]triazole Structure

1-[(4-phenylmet...

~88%

4-(triazol-1-ylmethoxy)phenol Structure

4-(triazol-1-yl...