2β,3β,5-trihydroxy-5α-cholestan-6-one | 14858-09-4

• 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: 2β,3β,5-trihydroxy-5α-cholestan-6-one
• 英文别名: 2β,3β,5α-trihydroxycholestan-6-one；2β,3β,5-Trihydroxy-5α-cholestan-6-on；Cholestan-2β,3β,5α-triol-6-on；(2S,3R,5R,8S,9S,10R,13R,14S,17R)-2,3,5-trihydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-one
• CAS: 14858-09-4
• 化学式: C₂₇H₄₆O₄
• 分子量: 434.66
• InChiKey: KGDATIYAPDSOHB-FESAEEERSA-N

物化性质

• 沸点：
  545.9±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2β,3β,5-trihydroxy-5α-cholestan-6-one 在 吡啶 、 氯化亚砜 作用下， 生成 2β,3β-diacetoxycholest-4-en-6-one
  参考文献：
  名称：

  Synthesis of Cytotoxic 6E-Hydroximino-4-ene Steroids:  Structure/Activity Studies

  摘要：

  In an effort to determine the pharmaceutical utility and the structural requirements for activity against various tumor cell lines, several 6E-hydroximino-4-ene steroids with different side chains and degrees of unsaturation on ring A were synthesized in our laboratory. Evaluation of the synthesized compounds for cytotoxicity against P-388, A-549, HT-29, and MEL-28 tumor cells revealed that some important structural features are required for activity. The presence of a cholesterol-type side chain, which appears to play a major role in determining the biological activity, the existence of a ketone functionality at C-3, and an elevated degree of oxidation on ring A all result in higher bioactivity than other structural motifs.

  DOI：

  10.1021/jm010867n
• 作为产物：
  描述：

  3β-tosyloxy-5-hydroxy-5α-cholestan-6-one 在 N-甲基吗啉 、 四氧化锇 、 四丁基硫酸氢铵 、 lithium bromide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 88.0h， 生成 2β,3β,5-trihydroxy-5α-cholestan-6-one
  参考文献：
  名称：

  Synthesis of Cytotoxic 6E-Hydroximino-4-ene Steroids:  Structure/Activity Studies

  摘要：

  In an effort to determine the pharmaceutical utility and the structural requirements for activity against various tumor cell lines, several 6E-hydroximino-4-ene steroids with different side chains and degrees of unsaturation on ring A were synthesized in our laboratory. Evaluation of the synthesized compounds for cytotoxicity against P-388, A-549, HT-29, and MEL-28 tumor cells revealed that some important structural features are required for activity. The presence of a cholesterol-type side chain, which appears to play a major role in determining the biological activity, the existence of a ketone functionality at C-3, and an elevated degree of oxidation on ring A all result in higher bioactivity than other structural motifs.

  DOI：

  10.1021/jm010867n

文献信息

• Circular dichroism of steroidal and related cisoid α,β-unsaturated ketones. Part I.
  作者：Jadwiga Frelek、Wojciech J. Szczepek、Hans Peter Weiß

  DOI：10.1016/s0957-4166(00)86086-3

  日期：1993.3

  Some steroidal and related cisoid conjugated enones have been synthesized and their circular dichroism (CD) has been investigated. The relation between structure and observed Cotton effects (CE's) is discussed in terms of previously published rules. It is shown that CD spectra of these compounds are influenced by substituents located in the allylic axial or equatorial as well as α′-axial or equatorial

  已经合成了一些甾体和相关的类固醇共轭烯酮，并且已经研究了它们的圆二色性（CD）。结构和观察到的棉花效应（CE's）之间的关系是根据以前发布的规则进行讨论的。结果表明，这些化合物的CD光谱受位于烯丙基轴向或赤道以及α'轴向或赤道位置的取代基的影响。
• Mehrwertige Alkohole aus Sterinen und Sterinderivaten, VI Steroide mit Strukturmerkmalen des Ecdysons und der Elatericine
  作者：Hans Lettré、Jürgen Greiner、Klaus Rutz、Lothar Hofmann、Alfons Egle、Wilfried Bieger

  DOI：10.1002/jlac.19727580109

  日期：1972.7.12

  Aus Litho-, Desoxy- und Chenodesoxycholsäure (1a – c) wurden über die Homosäuren 5a – c die tert.-C25-Carbinole 7a – c dargestellt. Cholesterin ließ sich in das Ecdyson-analoge Produkt 18b umwandeln. Hyodesoxy- und Homohyodesoxycholsäure wurden in die Tetrole 33a, b übergeführt. Aus 34a – d wurden die Steroide 37a – d mit diosphenolischer Struktur gewonnen.

  AUS Litho-，Desoxy- UNDChenodesoxycholsäure（1A - C ^）wurden黚死Homosäuren 5A - Ç模具叔-C 25 -Carbinole 7A - Ç dargestellt。位于Das Ecdyson-Analoge Produkt 18b umwandeln中的胆固醇。Hyodesoxy- UNDHomohyodesoxycholsäurewurden裸片Tetrole部33a，b übergeführt。Aus 34a – d沸腾的硬脂酸酯37a – d mit diosphenolischer Struktur gewonnen。
• Synthesis and plant growth promoting activity of polyhydroxylated ketones bearing the 5α-hydroxy-6-oxo moiety and cholestane side chain
  作者：Anielka Rosado-Abón、Guadalupe de Dios-Bravo、Rogelio Rodríguez-Sotres、Martín A. Iglesias-Arteaga

  DOI：10.1016/j.steroids.2012.01.004

  日期：2012.4

  Three polyhydroxylated ketones bearing the 5alpha-hydroxy-6-oxo moiety were obtained from cholesterol. Two of them show plant growth promoting activity in the bean's second internode bioassay. The obtained results indicate that the presence of the 5alpha-hydroxy-6-oxo moiety may be capable to induce plant growth promotion even the absence oxygenated functions in the side chain.

  从胆固醇获得三个带有5α-羟基-6-氧代部分的多羟基化酮。他们中的两个在豆子的第二节间生物测定中显示出促进植物生长的活性。获得的结果表明，即使在侧链中不存在氧化功能，5α-羟基-6-氧代部分的存在也能够诱导植物生长促进。
• Kocovsky,P.; Cerny,V., Collection of Czechoslovak Chemical Communications, 1977, vol. 42, p. 163 - 172
  作者：Kocovsky,P.、Cerny,V.

  DOI：——

  日期：——
• Synthesis of Cytotoxic 6<i>E</i>-Hydroximino-4-ene Steroids:  Structure/Activity Studies
  作者：Noé Deive、Jaime Rodríguez、Carlos Jiménez

  DOI：10.1021/jm010867n

  日期：2001.8.1

  In an effort to determine the pharmaceutical utility and the structural requirements for activity against various tumor cell lines, several 6E-hydroximino-4-ene steroids with different side chains and degrees of unsaturation on ring A were synthesized in our laboratory. Evaluation of the synthesized compounds for cytotoxicity against P-388, A-549, HT-29, and MEL-28 tumor cells revealed that some important structural features are required for activity. The presence of a cholesterol-type side chain, which appears to play a major role in determining the biological activity, the existence of a ketone functionality at C-3, and an elevated degree of oxidation on ring A all result in higher bioactivity than other structural motifs.