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

6-Aryl-1, 4-dihydro-benzo [d][1, 3] oxazin-2-ones: a novel class of potent, selective, and orally active nonsteroidal progesterone receptor antagonists

P Zhang, EA Terefenko, A Fensome…

Index: Zhang, Puwen; Terefenko, Eugene A.; Fensome, Andrew; Wrobel, Jay; Winneker, Richard; Lundeen, Scott; Marschke, Keith B.; Zhang, Zhiming Journal of Medicinal Chemistry, 2002 , vol. 45, # 20 p. 4379 - 4382

Full Text: HTML

Citation Number: 67

Abstract

Novel 6-aryl-1, 4-dihydro-benzo [d][1, 3] oxazin-2-ones were synthesized and tested as progesterone receptor (PR) antagonists. These compounds were potent and showed good selectivity for PR over other steroid receptors such as the glucocorticoid and androgen receptors (eg, greater than 80-fold selectivity at PR for 4h). Numerous 6-aryl benzoxazinones (eg, 4h-j) were active orally in the uterine decidualization and component ...

1-Bromo-3-fluorobenzene Structure

1-Bromo-3-fluor...

6-Bromo-4,4-dimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one Structure

6-Bromo-4,4-dim...

~%

6-(3-FLUOROPHENYL)-4,4-DIMETHYL-1H-BENZO[D][1,3]OXAZIN-2(4H)-ONE Structure

6-(3-FLUOROPHEN...

2-(2-AMINO-5-BROMOPHENYL)PROPAN-2-OL Structure

2-(2-AMINO-5-BR...

~%

6-(3-FLUOROPHENYL)-4,4-DIMETHYL-1H-BENZO[D][1,3]OXAZIN-2(4H)-ONE Structure

6-(3-FLUOROPHEN...

2-(2-AMINO-5-BROMOPHENYL)PROPAN-2-OL Structure

2-(2-AMINO-5-BR...

~%

6-(3-METHOXYPHENYL)-4,4-DIMETHYL-1H-BENZO[D][1,3]OXAZIN-2(4H)-ONE Structure

6-(3-METHOXYPHE...

4-Chlorophenylboronic acid Structure

4-Chlorophenylb...

6-Bromo-4,4-dimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one Structure

6-Bromo-4,4-dim...

~79%

6-(3-CHLOROPHENYL)-4,4-DIMETHYL-1H-BENZO[D][1,3]OXAZIN-2(4H)-ONE Structure

6-(3-CHLOROPHEN...

2-(2-AMINO-5-BROMOPHENYL)PROPAN-2-OL Structure

2-(2-AMINO-5-BR...

~%

6-(3-CHLOROPHENYL)-4,4-DIMETHYL-1H-BENZO[D][1,3]OXAZIN-2(4H)-ONE Structure

6-(3-CHLOROPHEN...

4-Bromo-2-chloro-1-fluorobenzene Structure

4-Bromo-2-chlor...

Boronic acid, (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)- (9CI) Structure

Boronic acid, (...

~%

6-(3-CHLORO-4-FLUOROPHENYL)-4,4-DIMETHYL-1H-BENZO[D][1,3]OXAZIN-2(4H)-ONE Structure

6-(3-CHLORO-4-F...

6-Bromo-4,4-dimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one Structure

6-Bromo-4,4-dim...

~%

6-(3-CHLORO-4-FLUOROPHENYL)-4,4-DIMETHYL-1H-BENZO[D][1,3]OXAZIN-2(4H)-ONE Structure

6-(3-CHLORO-4-F...

2-(2-AMINO-5-BROMOPHENYL)PROPAN-2-OL Structure

2-(2-AMINO-5-BR...

~%

6-(3-CHLORO-4-FLUOROPHENYL)-4,4-DIMETHYL-1H-BENZO[D][1,3]OXAZIN-2(4H)-ONE Structure

6-(3-CHLORO-4-F...

4-Bromo-2-fluorobenzonitrile Structure

4-Bromo-2-fluor...

Boronic acid, (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)- (9CI) Structure

Boronic acid, (...

~%

5-(4,4-DIMETHYL-2-OXO-2,4-DIHYDRO-1H-BENZO[D][1,3]OXAZIN-6-YL)-2-FLUOROBENZONITRILE Structure

5-(4,4-DIMETHYL...

6-Bromo-4,4-dimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one Structure

6-Bromo-4,4-dim...

~%

5-(4,4-DIMETHYL-2-OXO-2,4-DIHYDRO-1H-BENZO[D][1,3]OXAZIN-6-YL)-2-FLUOROBENZONITRILE Structure

5-(4,4-DIMETHYL...

2-(2-AMINO-5-BROMOPHENYL)PROPAN-2-OL Structure

2-(2-AMINO-5-BR...

~%

5-(4,4-DIMETHYL-2-OXO-2,4-DIHYDRO-1H-BENZO[D][1,3]OXAZIN-6-YL)-2-FLUOROBENZONITRILE Structure

5-(4,4-DIMETHYL...

3-Chloro-5-fluorobenzonitrile Structure

3-Chloro-5-fluo...

Boronic acid, (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)- (9CI) Structure

Boronic acid, (...

~82%

3-(4,4-DIMETHYL-2-OXO-2,4-DIHYDRO-1H-BENZO[D][1,3]OXAZIN-6-YL)-5-FLUOROBENZONITRILE Structure

3-(4,4-DIMETHYL...

6-Bromo-4,4-dimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one Structure

6-Bromo-4,4-dim...

~%

3-(4,4-DIMETHYL-2-OXO-2,4-DIHYDRO-1H-BENZO[D][1,3]OXAZIN-6-YL)-5-FLUOROBENZONITRILE Structure

3-(4,4-DIMETHYL...

2-(2-AMINO-5-BROMOPHENYL)PROPAN-2-OL Structure

2-(2-AMINO-5-BR...

~%

3-(4,4-DIMETHYL-2-OXO-2,4-DIHYDRO-1H-BENZO[D][1,3]OXAZIN-6-YL)-5-FLUOROBENZONITRILE Structure

3-(4,4-DIMETHYL...

3-Chloro-5-fluorobromobenzene Structure

3-Chloro-5-fluo...

Boronic acid, (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)- (9CI) Structure

Boronic acid, (...

~%

6-(3-CHLORO-5-FLUOROPHENYL)-4,4-DIMETHYL-1H-BENZO[D][1,3]OXAZIN-2(4H)-ONE Structure

6-(3-CHLORO-5-F...

6-Bromo-4,4-dimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one Structure

6-Bromo-4,4-dim...

~%

6-(3-CHLORO-5-FLUOROPHENYL)-4,4-DIMETHYL-1H-BENZO[D][1,3]OXAZIN-2(4H)-ONE Structure

6-(3-CHLORO-5-F...

2-(2-AMINO-5-BROMOPHENYL)PROPAN-2-OL Structure

2-(2-AMINO-5-BR...

~%

6-(3-CHLORO-5-FLUOROPHENYL)-4,4-DIMETHYL-1H-BENZO[D][1,3]OXAZIN-2(4H)-ONE Structure

6-(3-CHLORO-5-F...

2-(2-AMINO-5-BROMOPHENYL)PROPAN-2-OL Structure

2-(2-AMINO-5-BR...

~%

Boronic acid, (1,4-dihydro-4,4-dimethyl-2-oxo-2H-3,1-benzoxazin-6-yl)- (9CI) Structure

Boronic acid, (...

6-Bromo-4,4-dimethyl-1,4-dihydrobenzo[d][1,3]oxazin-2-one Structure

6-Bromo-4,4-dim...

~%

3-(4,4-DIMETHYL-2-OXO-2,4-DIHYDRO-1H-BENZO[D][1,3]OXAZIN-6-YL)BENZONITRILE Structure

3-(4,4-DIMETHYL...

2-(2-AMINO-5-BROMOPHENYL)PROPAN-2-OL Structure

2-(2-AMINO-5-BR...

~%

3-(4,4-DIMETHYL-2-OXO-2,4-DIHYDRO-1H-BENZO[D][1,3]OXAZIN-6-YL)BENZONITRILE Structure

3-(4,4-DIMETHYL...

2-(2-AMINO-5-BROMOPHENYL)PROPAN-2-OL Structure

2-(2-AMINO-5-BR...

~%

6-(2-CHLOROPHENYL)-4,4-DIMETHYL-1H-BENZO[D][1,3]OXAZIN-2(4H)-ONE Structure

6-(2-CHLOROPHEN...