(1'R,5'S,9'R,10'S,13'S)-5'-methylspiro[1,3-dioxolane-2,15'-11,18-dioxapentacyclo[11.4.1.01,13.02,10.05,9]octadec-2-ene]-6'-one | 930587-81-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: (1'R,5'S,9'R,10'S,13'S)-5'-methylspiro[1,3-dioxolane-2,15'-11,18-dioxapentacyclo[11.4.1.01,13.02,10.05,9]octadec-2-ene]-6'-one
• CAS: 930587-81-8
• 化学式: C₁₉H₂₄O₅
• 分子量: 332.397
• InChiKey: CVYAYWIDOHKUSN-HLJGMIKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1'R,5'S,9'R,10'S,13'S)-5'-methylspiro[1,3-dioxolane-2,15'-11,18-dioxapentacyclo[11.4.1.01,13.02,10.05,9]octadec-2-ene]-6'-one 在 CuCN*2LiCl 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 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：

  (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 二氯甲烷 、 苯 为溶剂， 反应 19.0h， 生成 (1'R,5'S,9'R,10'S,13'S)-5'-methylspiro[1,3-dioxolane-2,15'-11,18-dioxapentacyclo[11.4.1.01,13.02,10.05,9]octadec-2-ene]-6'-one
  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

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。
• US7763648B2
  申请人：——

  公开号：US7763648B2

  公开（公告）日：2010-07-27
• Synthesis and identification of novel oxa-steroids as progesterone receptor antagonists
  作者：Fu-An Kang、George Allan、Jihua Guan、Nareshkumar Jain、Olivia Linton、Pamela Tannenbaum、Jun Xu、Peifang Zhu、Joseph Gunnet、Xin Chen、Keith Demarest、Scott Lundeen、Zhihua Sui

  DOI：10.1016/j.bmcl.2006.11.062

  日期：2007.2

  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.