7-methylene-cholest-5-en-3β-ol | 78799-79-8

• 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: 7-methylene-cholest-5-en-3β-ol
• 英文别名: 7-Methylen-cholest-5-en-3β-ol；7-Methylenecholesterol；(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-7-methylidene-1,2,3,4,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ol
• CAS: 78799-79-8
• 化学式: C₂₈H₄₆O
• 分子量: 398.673
• InChiKey: YOLRZVOKMHRJKY-NMMCDMEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  7-methylene-cholest-5-en-3β-ol 在 Wilkinson's catalyst 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 (3S,7S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-7,10,13-trimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol 、 (3S,7R,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-Dimethyl-hexyl)-7,10,13-trimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
  参考文献：
  名称：

  A stereoselective synthesis of 7β-phenyl and 7β-methylcholesterol

  摘要：

  A stereoselective synthesis of 7beta-phenylcholesterol and 7beta-methylcholesterol is described.Cholesterol is an immensely important biological molecule. Its biosynthesis,1 conversion to steroid hormones2,3 and even its intracellular esterification4 (cholesterol acyltransferase, ACAT) form important areas of research. Cholesterol is metabolized in the body to bile acids in which the rate limiting step is the conversion of cholesterol to 7alpha-hydroxycholesterol by the enzyme 7alpha-hydroxylase. 5 Substituents of cholesterol at the 7 position should metabolically stabilize the molecule. 7Alpha-substituted steroids are conveniently prepared and have shown interesting antiprogestational,6 antiestrogen,7 antiandrogen,8 aldosterone antagonist9 and aromatase8 inhibitory activities. Chemistry for the stereoselective synthesis of 7beta-substituted steroids is relatively less developed.10 In this paper, we report a new stereoselective synthesis of 7beta-phenyl and 7beta-methylcholesterol. Chemistry described here should be applicable to the preparation of other 7beta-substituted steroids.

  DOI：

  10.1016/s0040-4039(00)60344-1
• 作为产物：
  描述：

  5-胆甾烯-3β-醇-7-酮 、 trimethylsilylmethyllithium 在 sodium hydride 作用下， 生成 7-methylene-cholest-5-en-3β-ol
  参考文献：
  名称：

  A stereoselective synthesis of 7β-phenyl and 7β-methylcholesterol

  摘要：

  A stereoselective synthesis of 7beta-phenylcholesterol and 7beta-methylcholesterol is described.Cholesterol is an immensely important biological molecule. Its biosynthesis,1 conversion to steroid hormones2,3 and even its intracellular esterification4 (cholesterol acyltransferase, ACAT) form important areas of research. Cholesterol is metabolized in the body to bile acids in which the rate limiting step is the conversion of cholesterol to 7alpha-hydroxycholesterol by the enzyme 7alpha-hydroxylase. 5 Substituents of cholesterol at the 7 position should metabolically stabilize the molecule. 7Alpha-substituted steroids are conveniently prepared and have shown interesting antiprogestational,6 antiestrogen,7 antiandrogen,8 aldosterone antagonist9 and aromatase8 inhibitory activities. Chemistry for the stereoselective synthesis of 7beta-substituted steroids is relatively less developed.10 In this paper, we report a new stereoselective synthesis of 7beta-phenyl and 7beta-methylcholesterol. Chemistry described here should be applicable to the preparation of other 7beta-substituted steroids.

  DOI：

  10.1016/s0040-4039(00)60344-1

文献信息

• Bioerodible implant for long-term drug delivery and associated methods of manufacture and use
  申请人：Gesea Biosciences Inc.

  公开号：US10188602B2

  公开（公告）日：2019-01-29

  A drug delivery system is provided in the form of a controlled release, bioerodible pellet for subdermal implantation. The pellet is bioerodible, and provides for the sustained release of a pharmacologically active agent over an extended time period. As such, the drug delivery system finds significant utility in chronic drug administration. Bioerosion products are water soluble, bioresorbed, or both, obviating the need for surgical removal of the implant. Methods for manufacturing and using the drug delivery system are also provided.

  一种药物输送系统是一种用于皮下植入的控释可生物降解颗粒。这种颗粒具有生物可降解性，可在较长时间内持续释放药理活性物质。因此，这种给药系统在慢性给药方面具有重要作用。生物侵蚀产品可溶于水、被生物吸收或两者兼而有之，因此无需通过手术移除植入物。此外，还提供了制造和使用该给药系统的方法。
• Bioerodible contraceptive implant and methods of use thereof
  申请人：Gesea Biosciences Inc.

  公开号：US10406099B2

  公开（公告）日：2019-09-10

  A contraceptive drug delivery system is provided in the form of a controlled release, bioerodible pellet for subdermal implantation. The pellet is bioerodible, and provides for the sustained release of a contraceptive agent over an extended time period. Bioerosion products are water soluble, bioresorbed, or both, obviating the need for surgical removal of the implant. Methods of using the drug delivery system, including in female contraception, are also provided.

  一种避孕药物给药系统是一种用于皮下植入的控释生物可塑颗粒。这种颗粒可生物降解，可在较长的时间内持续释放避孕药物。生物腐蚀产品可溶于水、被生物吸收或两者兼而有之，因此无需通过手术取出植入物。此外，还提供了使用该给药系统的方法，包括用于女性避孕的方法。
• Synthesis of Steroidal Methylene Compounds by the Wittig Reaction¹
  作者：Franz Sondheimer、Raphael Mechoulam

  DOI：10.1021/ja01575a054

  日期：1957.9
• BIOERODIBLE IMPLANT FOR LONG-TERM DRUG DELIVERY AND ASSOCIATED METHODS OF MANUFACTURE AND USE
  申请人：Gesea Biosciences Inc.

  公开号：EP3518896A1

  公开（公告）日：2019-08-07
• BIOERODIBLE CONTRACEPTIVE IMPLANT AND METHODS OF USE THEREOF
  申请人：Gesea Biosciences Inc.

  公开号：US20180085248A1

  公开（公告）日：2018-03-29

  A contraceptive drug delivery system is provided in the form of a controlled release, bioerodible pellet for subdermal implantation. The pellet is bioerodible, and provides for the sustained release of a contraceptive agent over an extended time period. Bioerosion products are water soluble, bioresorbed, or both, obviating the need for surgical removal of the implant. Methods of using the drug delivery system, including in female contraception, are also provided.