(7alpha)-胆甾烷-3,7-二醇 | 7554-76-9

• 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
• 中文名称: (7alpha)-胆甾烷-3,7-二醇
• 英文名称: 5α-cholestane-3β,7α-diol
• 英文别名: cholestane-3β,7α-diol；7α-hydroxycholestan-3β-ol；Cholestandiol-(3β,7α)；5α-cholestanediol-(3β.7α)；(10S)-3c.7t-Dihydroxy-10r.13c-dimethyl-17c-((R)-1.5-dimethyl-hexyl)-(5tH.8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；3β.7α-Dihydroxy-10.13-dimethyl-17β.((R)-1.5-dimethyl-hexyl)-5α-gonan；5α-Cholestandiol-(3β.7α)；7alpha-Hydroxycholestanol；(3S,5R,7R,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol
• CAS: 7554-76-9
• 化学式: C₂₇H₄₈O₂
• 分子量: 404.677
• InChiKey: APYVEUGLZHAHDJ-BOKMIASKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (7alpha)-胆甾烷-3,7-二醇 、 苯甲酰氯 在 吡啶 作用下， 生成 3β,7β-bis-benzoyloxy-5α-cholestane
  参考文献：
  名称：

  The Dehydration of the 7-Epimeric 3(β)-Acetoxycholestanols-7. Some Transformation Products of γ-Cholestenol

  摘要：

  DOI：

  10.1021/ja01248a022
• 作为产物：
  描述：

  acetic acid-(7α-hydroxy-5α-cholestanyl-(3β)-ester) 在 氢氧化钾 作用下， 生成 (7alpha)-胆甾烷-3,7-二醇
  参考文献：
  名称：

  The Dehydration of the 7-Epimeric 3(β)-Acetoxycholestanols-7. Some Transformation Products of γ-Cholestenol

  摘要：

  DOI：

  10.1021/ja01248a022

文献信息

• Compounds that are Analogs of Squalamine, Used as Antibacterial Agents
  申请人：VIRBAC

  公开号：US20180042942A1

  公开（公告）日：2018-02-15

  The invention relates to compounds of formula (I), to the pharmaceutical compositions comprising same, and to the use thereof in the treatment of bacterial, fungal, viral and parasitic infections or in the treatment of cancer in humans or animals. In formula (I), R1 and R2 are as defined in claim 1.

  这项发明涉及公式（I）的化合物，包括相同的药物组成，以及在人类或动物中用于治疗细菌、真菌、病毒和寄生虫感染或治疗癌症的用途。在公式（I）中，R1和R2如权利要求1中定义的那样。
• Regio- and Stereospecific Synthesis of Cholesterol Derivatives and Their Hormonal Activity inCaenorhabditis elegans
  作者：Arndt W. Schmidt、Thomas Doert、Sigrid Goutal、Margit Gruner、Fanny Mende、Teymuras V. Kurzchalia、Hans-Joachim Knölker

  DOI：10.1002/ejoc.200600394

  日期：2006.8

  identified. Herein, we describe the regio- and stereospecific synthesis of a number of cholesterol derivatives. The lithium–ammonia reduction of 4-cholesten-3-one was utilized to develop a general method for the introduction of diverse functional groups at C-4α of 5α-cholestan-3β-ol. Stereoselective functionalization at C-7 was achieved starting from 7-ketocholesterol derivatives. 6-Keto-5α-cholestan-3β-ol

  胆固醇对于线虫秀丽隐杆线虫的生存至关重要。最近的研究表明，胆固醇衍生物调节蠕虫生命周期中的两个过程：控制蜕皮和诱导特殊的非进食幼虫阶段。然而，胆固醇衍生信号分子的这些或任何其他功能的化学结构尚未确定。在此，我们描述了许多胆固醇衍生物的区域和立体特异性合成。4-cholesten-3-one 的锂-氨还原被用来开发一种通用方法，用于在 5α-cholestan-3β-ol 的 C-4α 处引入不同的官能团。C-7 的立体选择性功能化是从 7-酮胆固醇衍生物开始实现的。6-Keto-5α-cholestan-3β-ol 用于 C-6 和 C-7 的特定功能化。通过用这些化合物喂养不同遗传背景的蠕虫，研究了不同胆固醇衍生物的构效关系。我们的研究是确定线虫中激素活性与胆固醇不同位置取代关系的第一步。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim
• Potassium borohydride reductions of ketones absorbed into polymer supports: stereochemical effects
  作者：Josie C. Briggs、Philip Hodge

  DOI：10.1039/c39880000310

  日期：——

  The proportions of 6α-alcohol obtained from aqueous potassium borohydride reductions of 3β-hydroxy-5α-cholestan-6-one (1) absorbed into various polymers varied from 0 to 90% depending on the polymer used and whether or not a phase transfer catalyst was added; some other ketones show similar stereochemical effects, the greatest effects probably arising when the substrates are adsorbed to the inner surfaces

  由硼氢化钾水溶液还原3β-羟基-5α-胆甾醇-6-一（1）吸收而得的6α-醇的比例在0至90％之间变化，具体取决于所用的聚合物以及是否使用相转移催化剂加入; 其他一些酮类化合物也显示出相似的立体化学效应，当底物吸附在适当聚合物的内表面上时，最大的效应可能会出现。
• Inhibitory effect of oxygenated cholestan-3β-ol derivatives on the growth of Mycobacterium tuberculosis
  作者：Arndt W. Schmidt、Taylor A. Choi、Gabriele Theumer、Scott G. Franzblau、Hans-Joachim Knölker

  DOI：10.1016/j.bmcl.2013.09.013

  日期：2013.11

  A variety of cholestan-3 beta-ol derivatives, which are oxygenated at different positions of the steroid ring system, were prepared and tested for their inhibition of the Mycobacterium tuberculosis H(37)Rv strain. Several compounds showed significant antitubercular activities with MIC90 values in the range 4-8 mu M and low or non-detectable toxicity against mammalian cells. (c) 2013 Elsevier Ltd. All rights reserved.
• Maruyama, Sanae; Ogihara, Noriko; Adachi, Itsuko, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 5, p. 1847 - 1852
  作者：Maruyama, Sanae、Ogihara, Noriko、Adachi, Itsuko、Ohotawa, Junko、Morisaki, Masuo

  DOI：——

  日期：——