17-methylenandrost-4-en-3β-ol

• 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: 17-methylenandrost-4-en-3β-ol
• 英文别名: 17-methylene-androst-4-en-3β-ol；(3S,8S,9S,10R,13S,14S)-10,13-dimethyl-17-methylidene-1,2,3,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-ol
• 化学式: C₂₀H₃₀O
• 分子量: 286.458
• InChiKey: JMCNUPJJRLUBQN-SIRBJWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  17-methylenandrost-4-en-3β-ol 在 叔丁基过氧化氢 、 selenium(IV) oxide 、 环己酮 、 aluminum isopropoxide 作用下， 以 癸烷 、 二氯甲烷 、 苯 为溶剂， 反应 5.5h， 生成 C₂₀H₂₆O₂
  参考文献：
  名称：

  Synthesis of guggulsterone derivatives as potential anti-austerity agents against PANC-1 human pancreatic cancer cells

  摘要：

  E- and Z-guggulsterones and nine guggulsterone derivatives (GSDs) were synthesized and evaluated for their preferential cytotoxicity against human PANC-1 cell in nutrient deprived medium utilizing antiausterity strategy. Among the synthesized compounds, GSD-1 and GSD-7 showed potent cytotoxicity against PANC-1 cells under nutrient-deprived conditions in a concentration dependent manner, with a PC50 value of 1.6 mu M and 3.2 mu M, respectively. The effect of GSD-1 and GSD-7 was further evaluated in a real time using live cell imaging. Both of these compounds altered PANC-1 cell morphology, leading to cell death at sub micromolar concentration range. GSD-1 and GSD-7 also inhibited PANC-1 cell colony formation in a concentration-dependent manner. GSD-1 and GSD-7 are lead structure for the anti-austerity drug development.

  DOI：

  10.1016/j.bmcl.2020.126964
• 作为产物：
  描述：

  去氢表雄酮 、 甲基三苯基溴化膦 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 17-methylenandrost-4-en-3β-ol
  参考文献：
  名称：

  Synthesis of guggulsterone derivatives as potential anti-austerity agents against PANC-1 human pancreatic cancer cells

  摘要：

  E- and Z-guggulsterones and nine guggulsterone derivatives (GSDs) were synthesized and evaluated for their preferential cytotoxicity against human PANC-1 cell in nutrient deprived medium utilizing antiausterity strategy. Among the synthesized compounds, GSD-1 and GSD-7 showed potent cytotoxicity against PANC-1 cells under nutrient-deprived conditions in a concentration dependent manner, with a PC50 value of 1.6 mu M and 3.2 mu M, respectively. The effect of GSD-1 and GSD-7 was further evaluated in a real time using live cell imaging. Both of these compounds altered PANC-1 cell morphology, leading to cell death at sub micromolar concentration range. GSD-1 and GSD-7 also inhibited PANC-1 cell colony formation in a concentration-dependent manner. GSD-1 and GSD-7 are lead structure for the anti-austerity drug development.

  DOI：

  10.1016/j.bmcl.2020.126964

文献信息

• 17-Methyleneandrostan-3alpha-ol analogs as CRH inhibitors
  申请人：——

  公开号：US20030045514A1

  公开（公告）日：2003-03-06

  17-Methyleneandrostan-3&agr;-ol analogs are useful as corticotropin releasing hormone (CRH) inhibitors, and especially as anti-depressants, when administered to the vomeronasal organ. An improved synthesis of 17-methylenandrost-4-en-3&agr;-ol is disclosed.

  17-甲基雄烯烷-3α-醇类似物在给予腭咽器官时可作为促肾上腺皮质激素释放激素（CRH）抑制剂，特别是作为抗抑郁药物。一种改进的17-甲基雄烯-4-烯-3α-醇的合成方法被披露。
• 17-methylenandrostan-3alpha-ol analogs as CRH inhibitors
  申请人：Pherin Pharmaceuticals, Inc.

  公开号：US20030220309A1

  公开（公告）日：2003-11-27

  17-Methylenandrostan-3&agr;-ol analogs are useful as corticotropin releasing hormone (CRH) inhibitors, and especially as anti-depressants, when administered to the vomeronasal organ. An improved synthesis of 17-methylenandrost-4-en-3&agr;-ol is disclosed.

  17-Methylenandrostan-3α-ol类似物在给予挥发性鼻器官时，可用作促肾上腺皮质激素释放激素（CRH）抑制剂，特别是作为抗抑郁剂。本文披露了17-甲基烯雄甾-4-烯-3α-醇的改进合成方法。
• Novel androstanes for inducing hypothalamic effects
  申请人：——

  公开号：US20020103391A1

  公开（公告）日：2002-08-01

  The invention relates to novel, androstane steroids which are the ligand semiochemicals which bind to neuroepithelial receptors.

  该发明涉及一种新型的雄甾烷类固醇，它们是与神经上皮受体结合的配体信号化学物质。
• Androstane steroids as neurochemical initiators of change in human hypothalamic function and related pharmaceutical compositions and methods
  申请人：——

  公开号：US20020143001A1

  公开（公告）日：2002-10-03

  The invention relates to a method of altering hypothalamic function in an individual. The method comprises nasally administering a human semiochemical, e.g. an Androstane steroid, or a pharmaceutical composition containing a semiochemical, such that the ligand semiochemical binds to a specific neuroepithelial receptor. The steroid or steroids is/are preferably administered in the form of a pharmaceutical composition containing one or more pharmaceutically acceptable carriers. Other embodiments of the invention include pharmaceutical compositions containing the steroids.

  本发明涉及一种改变个体下丘脑功能的方法。该方法包括经鼻给予人类信息素，例如Androstane类固醇或含有信息素的药物组合物，使配体信息素与特定神经上皮受体结合。该类固醇通常以含有一种或多种药用载体的药物组合物的形式给予。本发明的其他实施方式包括含有该类固醇的药物组合物。
• ANDROSTANE STEROIDS AS NEUROCHEMICAL INITIATORS OF CHANGE IN HUMAN HYPOTHALAMIC FUNCTION AND RELATED PHARMACEUTICAL COMPOSITIONS AND METHODS
  申请人：PHERIN CORPORATION

  公开号：EP0711169A1

  公开（公告）日：1996-05-15