5α-methoxycholestane-3β,6β-diol | 2515-22-2

• 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: 5α-methoxycholestane-3β,6β-diol
• 英文别名: 5α-methoxycholesta-3β,6β-diol；methyl-(3β.6β-dihydroxy-5α-cholestanyl-(5))-ether；(10R)-3c.6c-Dihydroxy-5t-methoxy-10r.13c-dimethyl-17c-((R)-1.5-dimethyl-hexyl)-(8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；Methyl-(3β.6β-dihydroxy-5α-cholestanyl-(5))-aether；5-Methoxy-5α-cholestandiol-(3β.6β)；3β,6β-Dihydroxy-5α-methoxy-cholestan；(3S,5R,6R,8S,9S,10R,13R,14S,17R)-5-methoxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,6-diol
• CAS: 2515-22-2
• 化学式: C₂₈H₅₀O₃
• 分子量: 434.703
• InChiKey: MATSKTCJBVHZDF-VJENCBHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5α-methoxycholestane-3β,6β-diol 在 chromium(VI) oxide 作用下， 以 丙酮 为溶剂， 生成 5α-Methoxy-cholestan-3,6-dion
  参考文献：
  名称：

  5α-羟基类固醇的酸催化反应-III：westphalen重排

  摘要：

  对威斯特伐伦重排的动力学研究表明，该反应通过硫酸酯进行，该硫酸酯产生C 5碳离子。描述了6β-取代基对反应过程的影响。

  DOI：

  10.1016/s0040-4020(01)98321-8
• 作为产物：
  描述：

  5α-cholestane-3β,5,6β-triol 3,6-diacetate 在 氢氧化钾 、 硫酸 作用下， 生成 5α-methoxycholestane-3β,6β-diol
  参考文献：
  名称：

  Hattori, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1939, vol. 59, p. 416; engl. Ref. S. 131

  摘要：

  DOI：

文献信息

• Selective Cytotoxicity of Oxysterols through Structural Modulation on Rings A and B. Synthesis, in Vitro Evaluation, and SAR
  作者：João F. S. Carvalho、M. Manuel Cruz Silva、João N. Moreira、Sérgio Simões、M. Luisa Sá e Melo

  DOI：10.1021/jm200803d

  日期：2011.9.22

  Chemically diverse oxysterols were prepared and evaluated for cytotoxicity, aiming to push forward potency and selectivity. They were tested against seven cancer (HT-29, HepG2, A549, PC3, LAMA-84, MCF-7, and SH-SYSY) and two noncancerous cell lines (ARPE-19 and BJ). The influence of the oxidation pattern on rings A and B was studied. Oxygen functionalities on ring B, such as oxo, oxime, acetamide, acetate, and alkoxy, were evaluated. Most oxysterols were cytotoxic in the low micromolar range, with emphasis to the tetrols 14 and 34, the 6 beta methoxy and acetoxy derivatives 21 and 45, and the oxime 28. In general, the oxysterols were more toxic to cancer cells and a set of compounds (9, 14, 21, 28, 45) with very high selectivity was identified. The cytotoxicity of 3 beta-acetates was lower than that of the parent alcohols, although incubation for a longer period rendered them equally cytotoxic, pointing them as potential prodrugs of oxysterols.
• Ishiguro, Masaji; Saito, Hiromitsu; Ikekawa, Nobuo, Journal of the Chemical Society. Perkin transactions I, 1980, p. 2507 - 2510
  作者：Ishiguro, Masaji、Saito, Hiromitsu、Ikekawa, Nobuo

  DOI：——

  日期：——
• Hattori, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1939, vol. 59, p. 416; engl. Ref. S. 131
  作者：Hattori

  DOI：——

  日期：——
• Acid catalysed reactions of 5α-hydroxy-steroids—III
  作者：J.W. Blunt、A. Fischer、M.P. Hartshorn、F.W. Jones、D.N. Kirk、S.W. Yoong

  DOI：10.1016/s0040-4020(01)98321-8

  日期：1965.1

  A kinetic study of the Westphalen rearrangement has revealed that the reaction proceeds through a sulphate ester which gives rise to a C5 carbonium ion. The effect of the 6β-substituent on the course of the reaction is described.

  对威斯特伐伦重排的动力学研究表明，该反应通过硫酸酯进行，该硫酸酯产生C 5碳离子。描述了6β-取代基对反应过程的影响。