2β,3β-diacetoxycholest-4-en-6-one | 65082-77-1

• 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-diacetoxycholest-4-en-6-one
• 英文别名: 2β,3β-Diacetoxycholest-4-en-6-on；[(2S,3R,8S,9S,10R,13R,14S,17R)-3-acetyloxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-6-oxo-1,2,3,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-2-yl] acetate
• CAS: 65082-77-1
• 化学式: C₃₁H₄₈O₅
• 分子量: 500.719
• InChiKey: PWEVPGBFNABIDD-JVJNKKEYSA-N

物化性质

• 沸点：
  568.5±50.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2β,3β-diacetoxycholest-4-en-6-one 在 Pd/SrCO₃ 氢气 、 溴 、 lithium carbonate 、 lithium bromide 作用下， 以 氯仿 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 169.0h， 生成 2β,3β-diacetoxy-5α-chloest-7-en-6-one
  参考文献：
  名称：

  Akhrem, A. A.; Lakhvich, F. A.; Khripach, V. A., Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, # 6, p. 1116 - 1122

  摘要：

  DOI：
• 作为产物：
  描述：

  3β-tosyloxy-5-hydroxy-5α-cholestan-6-one 在 N-甲基吗啉 、 吡啶 、 四氧化锇 、 氯化亚砜 、 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-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

文献信息

• Kocovsky,P.; Cerny,V., Collection of Czechoslovak Chemical Communications, 1977, vol. 42, p. 2415 - 2437
  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.
• Akhrem, A. A.; Lakhvich, F. A.; Khripach, V. A., Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, # 6, p. 1116 - 1122
  作者：Akhrem, A. A.、Lakhvich, F. A.、Khripach, V. A.、Kovganko, N. V.

  DOI：——

  日期：——