6β-methoxycholestane-3β,5α-diol | 13163-79-6

• 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: 6β-methoxycholestane-3β,5α-diol
• 英文别名: methyl-(3β.5-dihydroxy-5α-cholestanyl-(6β))-ether；(10R)-3c.5t-Dihydroxy-6c-methoxy-10r.13c-dimethyl-17c-((R)-1.5-dimethyl-hexyl)-(8cH.9tH.14tH)-hexadecahydro-1H-cyclopenta[a]phenanthren；Methyl-(3β.5-dihydroxy-5α-cholestanyl-(6β))-aether；6β-Methoxy-5α-cholestandiol-(3β.5)；3β,5α-Dihydroxy-6β-methoxy-cholestan；6β-Methoxy-cholestan-3β,5α-diol；(3S,5R,6R,8S,9S,10R,13R,14S,17R)-6-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-3,5-diol
• CAS: 13163-79-6
• 化学式: C₂₈H₅₀O₃
• 分子量: 434.703
• InChiKey: FVOWWSRLGCNEGB-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：

  6β-methoxycholestane-3β,5α-diol 在 吡啶 、 chromium(VI) oxide 、 氢氧化钾 、 硫酸 、 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 生成 3β-Acetoxy-6β-methoxy-cholest-4-en
  参考文献：
  名称：

  Julia,S. et al., Bulletin de la Societe Chimique de France, 1966, p. 2277 - 2283

  摘要：

  DOI：
• 作为产物：
  描述：

  胆甾烷-3,5,6-三醇 在 吡啶 、 xylene 作用下， 生成 6β-methoxycholestane-3β,5α-diol
  参考文献：
  名称：

  ÜberSteroide和性激素。胆固醇和反式脱氢雄激素

  摘要：

  DOI：

  10.1002/hlca.19470300609

文献信息

• 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：——
• 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.
• Kocovsky,P. et al., Collection of Czechoslovak Chemical Communications, 1979, vol. 44, p. 234 - 245
  作者：Kocovsky,P. et al.

  DOI：——

  日期：——
• Kocovsky,P.; Cerny,V., Collection of Czechoslovak Chemical Communications, 1978, vol. 43, p. 1933 - 1941
  作者：Kocovsky,P.、Cerny,V.

  DOI：——

  日期：——
• Über Steroide und Sexualhormone. Ein neuer Weg zur Herstellung der α-Oxyde von Cholesterin und trans-Dehydro-androsteron
  作者：A. Fürst、F. Koller

  DOI：10.1002/hlca.19470300609

  日期：1947.10.15