2,3,4,7,8,9,10,11,12,13,14,15,16,17-Tetradecahydro-10,13-dimethyl-1H-cyclopenta[A]phenanthren-3-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: 2,3,4,7,8,9,10,11,12,13,14,15,16,17-Tetradecahydro-10,13-dimethyl-1H-cyclopenta[A]phenanthren-3-OL
• 英文别名: 10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• 化学式: C₁₉H₃₀O
• 分子量: 274.4
• InChiKey: LYFPAZBMEUSVNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

文献信息

• [EN] NOVEL METHOD FOR SYNTHESIZING 25-OH CHOLESTEROL/CALCIFEDIOL FROM PHYTOSTEROL<br/>[FR] NOUVEAU PROCÉDÉ DE SYNTHÈSE DE 25-OH CHOLESTÉROL/CALCIFÉDIOL À PARTIR DE PHYTOSTÉROL
  申请人：FERMENTA BIOTECH LTD

  公开号：WO2020225830A1

  公开（公告）日：2020-11-12

  The present invention discloses novel method for synthesizing vegan 25-OH cholesterol/Calcifediol from inexpensive crude phytosterol. According to the method, Phytosterols are reacted to form corresponding i-steroid through tosylation and methanolysis. i-steroid on reductive ozonolysis to C-22 alcohol and conversion via C-22 tosylate to C-22 iodide in good yield. Coupling of C-22 tosylate with Grignard reagent of 4-bromo-2-methyl-2-[(trimethylsilyl)oxy] butane followed by deprotection yielded 25-OH cholesterol. In a process variant, nickel mediated conjugate addition of C-22 iodide to an electron deficient alkene ethyl acrylate and treating corresponding ester with methyl magnesium bromide as means of installing the side chain of 25-OH cholesterol in high yield. Further bromination reaction of 25-OH cholesterol diacetate followed by dehydrobromination using TBAF yielded 25-OH 7-dehydrocholesterol. Further photo reaction of 25-OH 7-dehydrocholesterol in to previtamin D3 using high or medium pressure mercury lamp and subsequent thermal reaction of previtamin D3 to 25-OH vitamin D3(Calcifediol) in good yield.

  本发明揭示了一种从廉价的原始植物甾醇合成素食25-OH胆固醇/钙化二醇的新方法。根据该方法，通过对烷基化和甲醇化反应形成相应的i-类固醇。i-类固醇通过还原臭氧化反应生成C-22醇，并通过C-22烷基磺酸酯转化为C-22碘化物，收率良好。将C-22烷基磺酸酯与4-溴-2-甲基-2-[(三甲基硅基)氧基]丁烷的Grignard试剂偶联，然后去保护基，得到25-OH胆固醇。在一个过程变体中，通过镍介导的C-22碘化物与电子亏损的烯烃乙基丙烯酸酯进行共轭加成，然后用甲基镁溴化物处理相应的酯，以高收率安装25-OH胆固醇的侧链。进一步，对25-OH胆固醇二乙酸酯进行溴化反应，随后使用TBAF进行脱溴反应，得到25-OH 7-脱氢胆固醇。进一步，将25-OH 7-脱氢胆固醇进行光反应，使用高压或中压汞灯，然后将previtamin D3进行热反应，得到25-OH维生素D3（钙化二醇），收率良好。
• Combination Of Dehydroepiandrosterone Or Dehydroepiandrosterone-Sulfate With An Anticholinergic Bronchodilator For Treatment Of Asthma Or Chronic Obstructive Pulmonary Disease
  申请人：Robinson Cynthia B.

  公开号：US20080279789A1

  公开（公告）日：2008-11-13

  A pharmaceutical or veterinary composition, comprises a first active agent selected from a dehydroepiandrosterone and/or dehydroepiandrosterone-sulfate, or a salt thereof, and a second active agent comprising an anticholinergic bronchodilator for the treatment of asthma, chronic obstructive pulmonary disease, or other respiratory diseases. The composition is provided in various formulations and in the form of a kit. The products of this patent are applied to the prophylaxis and treatment of asthma, chronic obstructive pulmonary disease, or other respiratory diseases.

  一种药物或兽医用组合物，包括第一活性成分，所述第一活性成分由去氢表雄酮和/或去氢表雄酮硫酸盐或其盐选出，以及第二活性成分，所述第二活性成分包括抗胆碱能支气管扩张剂，用于治疗哮喘、慢性阻塞性肺疾病或其他呼吸系统疾病。该组合物以各种配方和套装形式提供。该专利产品用于预防和治疗哮喘、慢性阻塞性肺疾病或其他呼吸系统疾病。
• COMBINATION OF DEHYDROEPIANDROSTERONE OR DEHYDROEPIANDROSTERONE-SULFATE WITH AN ANTICHOLINERGIC BRONCHODILATOR FOR TREATMENT OF ASTHMA OR CHRONIC OBSTRUCTIVE PULMONARY DISEASE
  申请人：Robinson Cynthia B.

  公开号：US20090285898A1

  公开（公告）日：2009-11-19

  A pharmaceutical or veterinary composition, comprises a first active agent selected from a dehydroepiandrosterone and/or dehydroepiandrosterone-sulfate, or a salt thereof, and a second active agent comprising an anticholinergic bronchodilator for the treatment of asthma, chronic obstructive pulmonary disease, or other respiratory diseases. The composition is provided in various formulations and in the form of a kit. The products of this patent are applied to the prophylaxis and treatment of asthma, chronic obstructive pulmonary disease, or other respiratory diseases.

  一种药物或兽医用组合物，包括第一活性剂，所述第一活性剂选自去氢表雄酮和/或去氢表雄酮硫酸盐或其盐，并且第二活性剂包括抗胆碱能支气管扩张剂，用于治疗哮喘、慢性阻塞性肺疾病或其他呼吸系统疾病。该组合物以多种配方和套装形式提供。本专利的产品用于预防和治疗哮喘、慢性阻塞性肺疾病或其他呼吸系统疾病。
• COMPOSITION COMPRENANT AU MOINS UNE OXAZOLINE POUR INHIBER LA MIGRATION DES CELLULES DE LANGERHANS,ET SES UTILISATIONS
  申请人：Laboratoires Expanscience

  公开号：EP1458349B1

  公开（公告）日：2014-11-05
• COMBINATION OF DEHYDROEPIANDROSTERONE OR DEHYDROEPIANDROSTERONE-SULFATE WITH A METHYLXANTHINE DERIVATIVE FOR TREATMENT OF ASTHMA OR CHRONIC OBSTRUCTIVE PULMONARY DISEASE
  申请人：Robinson Cynthia B.

  公开号：US20090285899A1

  公开（公告）日：2009-11-19

  A pharmaceutical or veterinary composition, comprises a first active agent selected from a dehydroepiandrosterone and/or dehydroepiandrosterone-sulfate, or a salt thereof, and a second active agent comprising a methylxanthine derivative for the treatment of asthma, chronic obstructive pulmonary disease, or other respiratory diseases. The composition is provided in various formulations and in the form of a kit. The products of this patent are applied to the prophylaxis and treatment of asthma, chronic obstructive pulmonary disease, or other respiratory diseases.