1,5-Dihydro-benzo[e][1,4]oxazepin-2(1H)-ones containing a 7-(5'-cyanopyrrol-2-yl) group as nonsteroidal progesterone receptor modulators.

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Kern JC, Terefenko EA, Fensome A, Unwalla R, Wrobel J, Cohen J, Zhu Y, Berrodin TJ, Yudt MR, Winneker RC, Zhang Z, Zhang P

1,5-Dihydro-benzo[e][1,4]oxazepin-2(1H)-ones containing a 7-(5'-cyanopyrrol-2-yl) group as nonsteroidal progesterone receptor modulators.

Bioorg Med Chem Lett. 2008 Sep 15;18(18):5015-7. doi: 10.1016/j.bmcl.2008.08.015. Epub 2008 Aug 9.

PubMed ID

18722119 [ View in PubMed

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Abstract

A series of novel 7-(5'-cyanopyrrol-2-yl) substituted benzo[1,4]oxazepin-2-ones were prepared and tested for their progesterone receptor (PR) agonist or antagonist activity in the alkaline phosphatase assay using the human T47D breast carcinoma cell line. Both PR agonists and antagonists were achieved with an appropriate choice of 5-substitution. Several analogs were potent PR agonists (e.g., 12 and 13) or PR antagonists (e.g., 18) with good selectivity over other steroid receptors.

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Mifepristone	Glucocorticoid receptor	IC 50 (nM)	0.6	N/A	N/A	Details
Mifepristone	Progesterone receptor	IC 50 (nM)	0.2	N/A	N/A	Details
Progesterone	Progesterone receptor	EC 50 (nM)	0.9	N/A	N/A	Details