Journal of Medicinal Chemistry

, volume 45 , issue 20 , pages 4379-4382

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

Puwen Zhang ¹

Eugene A. Terefenko ¹

Andrew Fensome ¹

Jay Wrobel ¹

Richard Winneker ¹

Scott Lundeen ¹

KEITH B. MARSCHKE ¹

Zhiming Zhang ¹

Hide authors affiliations Show authors affiliations: 1 affiliation

Chemical Sciences, Women's Health Research Institute, Wyeth Research, 500 Arcola Road, Collegeville, Pennsylvania 19426, and Ligand Pharmaceuticals, San Diego, California 92121 |

Publication type: Journal Article

Publication date: 2002-08-27

American Chemical Society (ACS)

Journal of Medicinal Chemistry

scimago Q1

wos Q1

SJR: 1.801

CiteScore: 11.5

Impact factor: 6.8

ISSN: 00222623, 15204804

DOI: 10.1021/jm025555e

Copy DOI

PubMed ID: 12238914

Drug Discovery

Molecular Medicine

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 (e.g., greater than 80-fold selectivity at PR for 4h). Numerous 6-aryl benzoxazinones (e.g., 4h−j) were active orally in the uterine decidualization and component C3 assays in the rats. In these in vivo models, 4h had potencies comparable to mifepristone (1).

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Cite this

GOST |

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GOST Copy

Zhang P. et al. 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 // Journal of Medicinal Chemistry. 2002. Vol. 45. No. 20. pp. 4379-4382.

GOST all authors (up to 50) Copy

Zhang P., Terefenko E. A., Fensome A., Wrobel J., Winneker R., Lundeen S., MARSCHKE K. B., Zhang Z. 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 // Journal of Medicinal Chemistry. 2002. Vol. 45. No. 20. pp. 4379-4382.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/jm025555e

UR - https://doi.org/10.1021/jm025555e

TI - 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

T2 - Journal of Medicinal Chemistry

AU - Zhang, Puwen

AU - Terefenko, Eugene A.

AU - Fensome, Andrew

AU - Wrobel, Jay

AU - Winneker, Richard

AU - Lundeen, Scott

AU - MARSCHKE, KEITH B.

AU - Zhang, Zhiming

PY - 2002

DA - 2002/08/27

PB - American Chemical Society (ACS)

SP - 4379-4382

IS - 20

VL - 45

PMID - 12238914

SN - 0022-2623

SN - 1520-4804

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2002_Zhang,

author = {Puwen Zhang and Eugene A. Terefenko and Andrew Fensome and Jay Wrobel and Richard Winneker and Scott Lundeen and KEITH B. MARSCHKE and Zhiming Zhang},

title = {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},

journal = {Journal of Medicinal Chemistry},

year = {2002},

volume = {45},

publisher = {American Chemical Society (ACS)},

month = {aug},

url = {https://doi.org/10.1021/jm025555e},

number = {20},

pages = {4379--4382},

doi = {10.1021/jm025555e}

}

MLA

Cite this

MLA Copy

Zhang, Puwen, et al. “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.” Journal of Medicinal Chemistry, vol. 45, no. 20, Aug. 2002, pp. 4379-4382. https://doi.org/10.1021/jm025555e.

Publisher

American Chemical Society (ACS)

Journal

Journal of Medicinal Chemistry

scimago Q1

wos Q1

SJR

1.801

CiteScore

11.5

Impact factor

6.8

ISSN

00222623 (Print)

15204804 (Electronic)