3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-ethyne | 91934-95-1

• 物质功能分类: 天然产物 - 甾体化合物
• 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: 3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-ethyne
• 英文别名: 3-(ethylenedioxy)estra-5α-hydroxy-11β-(4-N,N-dimethylaminophenyl)-17α-ethynyl-17β-hydroxy-9-ene；19-norpregn-9-en-20-yn-3-one, 11β-(4-N,N-dimethylaminophenyl)-5α,17β-dihydroxy-cyclic 1,2-ethanediyl ketal；3,3-ethylenedioxy-5a,17b-dihydroxy-11b-[4-(N,N-dimethylamino)phenyl]-19-nor-17a-pregn-9-ene-21-ethyne；(5'R,8'S,11'R,13'S,14'S,17'R)-11'-[4-(dimethylamino)phenyl]-17'-ethynyl-13'-methylspiro[1,3-dioxolane-2,3'-2,4,6,7,8,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene]-5',17'-diol
• CAS: 91934-95-1
• 化学式: C₃₀H₃₉NO₄
• 分子量: 477.644
• InChiKey: GMTUOJRBNRXCCQ-HTWSSZDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-ethyne 在 盐酸 、 高氯酸 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 7.5h， 生成 醋酸乌利司他
  参考文献：
  名称：

  [EN] NOVEL PROCESS AND INTERMEDIATE FOR PREPARATION OF ULIPRISTAL
  [FR] NOUVEAU PROCÉDÉ ET NOUVEL INTERMÉDIAIRE POUR PRÉPARATION D'ULIPRISTAL

  摘要：

  本发明涉及一种用于制备尤利普利斯塔尔（I）的新型工艺，该工艺包括将17-α-乙炔基-17-β-羟基-11-β-(4-N，N-二甲胺基苯基)-9-诺孕烯-4,9-二烯-3-酮（III）与苯基亚砜氯化物（IVa）或对硝基苯基亚砜氯化物（IVb）在有机碱和溶剂存在下反应，分别得到亚砜氧化物（Va）或（Vb）。亚砜氧化物（Va）或（Vb）与醇性溶剂中的碱金属烷氧化物反应，随后经过水酸处理。本发明还涉及新型中间体11-β-(4-N，N-二甲基氨基苯基)-21(对硝基苯基亚砜基)-19-诺孕烯-4(5)，9(10)，17(20) 20-四烯-3-酮（Vb）。

  公开号：

  WO2014060888A1
• 作为产物：
  描述：

  (5alpha,10alpha)-5,10-环氧-雌甾-9(11)-烯-3,17-二酮环3-(1,2-乙二基缩醛) 在 copper(l) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-ethyne
  参考文献：
  名称：

  Novel phosphorus-containing 17β-side chain mifepristone analogues as progesterone receptor antagonists

  摘要：

  A novel series of steroidal compounds were designed and synthesized with various phosphorus-containing groups on the 17 beta-side chain as progesterone receptor antagonists. The structure -activity relationships of these compounds are discussed. Selected compounds were tested in an rat progesterone-sensitive assay. Some of these compounds are more potent than mifepristone, with a better selectivity profile in differentiating progesterone receptor from glucocorticoid receptor.(C) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2006.07.003

文献信息

• 一种醋酸乌利司他及其中间体的制备方法
  申请人：成都化润药业有限公司

  公开号：CN104530169B

  公开（公告）日：2017-09-12

  本发明公开一种醋酸乌利司他及其中间体的制备方法，属于药物合成领域，醋酸乌利司他的制备方法包括以3,3‑(亚乙二氧基)‑19‑去甲孕甾‑5(10),9(11)‑二烯‑3,17‑二酮为原料，通过与乙炔钠或乙炔钾反应得到化合物III，再经过氧化物高选择性环氧化得到化合物IV，接着与4‑(N,N‑二甲基氨基)苯基溴化镁格氏试剂反应，得到化合物V，再与苯基次磺酸氯反应得到化合物VI，再分别与甲醇钠、亚磷酸三甲酯反应得到化合物VII，经水解并脱去保护基得到化合物VIII，最后乙酰化反应得到醋酸乌利司他，反应式如下：该方法合成路线短、反应条件温和、产品收率和纯度高、成本低廉且质量稳定可控，适合工业化生产。
• 11-PHOSPHOROUS STEROID DERIVATIVES USEFUL AS PROGESTERONE RECEPTOR MODULATORS
  申请人：Fiordeliso J. James

  公开号：US20070232570A1

  公开（公告）日：2007-10-04

  The present invention is directed to novel 11-phosphorous steroid derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by a progesterone or glucocorticoid receptor.

  本发明涉及新颖的11-磷酸类固醇衍生物，含有它们的药物组合物以及它们在治疗受孕激素或糖皮质激素受体调节的疾病和症状中的应用。
• 17-PHOSPHOROUS STEROID DERIVATIVES USEFUL AS PROGESTERONE RECEPTOR MODULATORS
  申请人：Jiang Weiqin

  公开号：US20070207982A1

  公开（公告）日：2007-09-06

  The present invention is directed to novel 17-phosphorous steroid derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by a progesterone or glucocorticoid receptor.

  本发明涉及新颖的17-磷类固醇衍生物，含有它们的药物组合物以及它们在治疗受孕激素或糖皮质激素受体调节的疾病和症状中的用途。
• A simple and convenient synthetic route to Ulipristal acetate
  作者：Yongguo Yu、Yun He、Yi Zhao、Li Hai、Yong Wu

  DOI：10.1016/j.steroids.2013.09.009

  日期：2013.12

  We set out to describe a new and efficient route for preparing Ulipristal acetate with a good yield. The selected epoxidization conditions gave out 80% of 5 alpha,10 alpha-epoxide 2a in the two diastereoisomers which greatly improved the yield of 11 beta-substituted isomer 4a. And phenyl-sulfinyl compound 6 was synthesized from ketone 5 directly treated with phenylsulfenyl chloride in the presence of triethylamine. These synthetic procedures is only 8 steps, less than currently reported in the literature, but more suitable for industrial process. (C) 2013 Elsevier Inc. All rights reserved.
• 11,21-Bisphenyl-19-norpregnane derivatives are selective antiglucocorticoids
  作者：R. Gebhard、H. van der Voort、W. Schuts、W. Schoonen

  DOI：10.1016/s0960-894x(97)00397-1

  日期：1997.9

  An efficient eight-step synthesis of 11,21-bisphenyl-19-norpregnane derivatives (10) starting from 19-norandrosta-4,9-diene-3,17-dione (5) is described. It is shown that specific combinations of polar substitutions on the 11- and the 21-phenylring in compounds (10) lead to selective antiglucocorticoids with relative high binding to the glucocorticoid receptor and almost negligible binding to the progesterone receptor. (C) 1997 Elsevier Science Ltd.