(8S,13S,14R)-7-oxa-estra-4,9-diene-3,17-dione | 924881-78-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (8S,13S,14R)-7-oxa-estra-4,9-diene-3,17-dione
• 英文别名: (3aR,3bS,11aS)-11a-methyl-3,3a,3b,5,8,9,10,11-octahydro-2H-indeno[4,5-c]isochromene-1,7-dione
• CAS: 924881-78-7
• 化学式: C₁₇H₂₀O₃
• 分子量: 272.344
• InChiKey: OJAOAAIVTHLNSZ-UAGQMJEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (8S,13S,14R)-7-oxa-estra-4,9-diene-3,17-dione 在 吡啶盐酸盐 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 22.0h， 生成 (5R,8S,11S,13S,14R,17S)-11-(4-dimethylaminophenyl)-13-methyl-17-prop-1-ynyl-1,2,3,4,5,6,8,11,12,13,14,15,16,17-tetradecahydro-7-oxacyclopenta[a]phenanthrene-3-spiro-2'-[1,3]dioxolane-5,17-diol
  参考文献：
  名称：

  Synthesis and identification of novel oxa-steroids as progesterone receptor antagonists

  摘要：

  A novel series of oxa-steroids 6 derived from (8S, 13S, 14R)-7-oxa-estra-4,9-diene-3,17-dione 1 have been synthesized and identified as potent and selective progesterone receptor antagonists. These novel oxa-steroids showed similar potency to mifepristone. Preliminary SAR study resulted in the most potent 17-phenylethynyl oxa-steroid 6i wih an IC50 of 1.4 nM. In contrast to the equipotent mifepristone toward the progesterone receptor (PR) and glucocorticoid receptor (GR), compound 6i had over 200-fold selectivity for PR over GR. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.062
• 作为产物：
  描述：

  (3aR,4S,7aS)-4-bromo-7a-methyloctahydro-1H-indene-1,5-dione 在 2,6-二甲基吡啶 、 盐酸 、 sodium periodate 、 四氧化锇 、 MS 4 Angstroem 、 sodium methylate 、 silica gel 、 potassium carbonate 、 戴斯-马丁氧化剂 、 potassium iodide 、 silver(l) oxide 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 90.5h， 生成 (8S,13S,14R)-7-oxa-estra-4,9-diene-3,17-dione
  参考文献：
  名称：

  Enantioselective synthesis of (8S,13S,14R)-7-oxa-estra-4,9-diene-3,17-dione

  摘要：

  The first enantioselective synthesis of (8S,13S,14R)-7-oxa-estra-4,9-diene-3,17-dione with the trans-C/D ring junction is described. Key features of the synthesis include Ag2O-mediated C-O bond formation, thermodynamically controlled axial-equatorial inversion, one-pot of halogen exchange and Co/Cr-mediated C-C bond formation, and intramolecular aldol condensations. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.11.042

文献信息

• OXA-STEROIDS DERIVATIVES AS SELECTIVE PROGESTERONE RECEPTOR MODULATORS
  申请人：Kang Fu-An

  公开号：US20070197635A1

  公开（公告）日：2007-08-23

  The present invention is directed to novel 7-oxa-estra-4,9-diene-3,17-dione derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by at least one progesterone or glucocorticoid receptor.

  本发明涉及新颖的7-氧杂雌甾-4,9-二烯-3,17-二酮衍生物，含有它们的药物组合物以及它们在治疗至少受孕激素或糖皮质激素受体调节的疾病和症状中的应用。
• COMPOSITIONS AND METHODS FOR SUPPRESSING ENDOMETRIAL PROLIFERATION
  申请人：Podolski Joseph S.

  公开号：US20100216756A1

  公开（公告）日：2010-08-26

  The subject matter of the instant invention is pertinent to the field of hormone therapy. More specifically, the subject matter of the instant invention concerns methods of treating estrogen-dependent conditions such as endometrial hyperplasia and endometrial cancer in a female undergoing estrogen and/or selective estrogen receptor modulator (SERM) therapy. The instant invention is also relevant to the suppression of endometrial proliferation. The instant invention is also relevant to the treatment of pain associated with endometriosis. The compositions for practicing the methods, comprising progesterone antagonists are also disclosed. Embodiments of the instant invention also disclose methods for identifying new selective progesterone receptor modulators for practicing disclosed methods of treatment.
• PROGESTERONE ANTAGONISTS SUCH AS CDB-4124 IN THE TREATMENT OF BREAST CANCER
  申请人：Podolski Joseph S.

  公开号：US20110053900A1

  公开（公告）日：2011-03-03

  The subject matter of the instant invention is pertinent to the field of cancer treatment. In particular, the instant invention is relevant to the treatment and/or prevention of breast cancer in a patient. Compositions for practicing the methods, comprising selective progesterone receptor modulators, which function as progesterone agonists in the uterus and as progesterone antagonists in the breast tissue and exhibit only low affinity for glucocorticoid and estrogen receptors, are also disclosed. Embodiments of the instant invention also disclose methods for preventing the development of breast cancer in patients undergoing hormone replacement therapy or estrogen therapy.
• PROGESTERONE ANTAGONISTS SUCH AS CDB-4124 IN THE TREATMENT OF ENDOMETRIOSIS, UTERINE FIBROIDS, DYSMENORRHEA, BREAST CANCER, ETC.
  申请人：Podolski Joseph S.

  公开号：US20130289008A1

  公开（公告）日：2013-10-31

  The present invention relates to methods of administering compositions comprising a progesterone receptor antagonist for use in treating estrogen-dependent conditions. The invention is also directed to methods for treating pain associated with endometriosis. The compositions may be administered to females with endometriosis as well as to females undergoing estrogen and/or selective estrogen receptor modulator (SERM) therapy. In certain embodiments, the invention provides a method for suppressing endometrial proliferation.
• Compositions and Methods for Suppressing Endometrial Proliferation
  申请人：REPROS THERAPEUTICS INC.

  公开号：US20140235602A1

  公开（公告）日：2014-08-21

  The subject matter of the instant invention is pertinent to the field of hormone therapy. More specifically, the subject matter of the instant invention concerns methods of treating estrogen-dependent conditions such as endometrial hyperplasia and endometrial cancer in a female undergoing estrogen and/or selective estrogen receptor modulator (SERM) therapy. The instant invention is also relevant to the suppression of endometrial proliferation. The instant invention is also relevant to the treatment of pain associated with endometriosis. The compositions for practicing the methods, comprising progesterone antagonists are also disclosed. Embodiments of the instant invention also disclose methods for identifying new selective progesterone receptor modulators for practicing disclosed methods of treatment.