3β-hydroxy-5β,6β-epoxycholestan-4β-yl acetate | 1162674-91-0

• 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: 3β-hydroxy-5β,6β-epoxycholestan-4β-yl acetate
• 英文别名: [(1S,2R,5S,6S,7S,9R,11S,12S,15R,16R)-5-hydroxy-2,16-dimethyl-15-[(2R)-6-methylheptan-2-yl]-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-6-yl] acetate
• CAS: 1162674-91-0
• 化学式: C₂₉H₄₈O₄
• 分子量: 460.698
• InChiKey: IKSPLBYLKWYPPB-DYIJDNIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酸乙烯酯 、 5,6-epoxycholestane-3β,4β-diol 在 Candida antarctica Novozym 435 lipase 作用下， 以 甲苯 为溶剂， 反应 168.0h， 以42%的产率得到5α,6α-epoxycholestane-3β,4β-diol
  参考文献：
  名称：

  Efficient Chemoenzymatic Synthesis, Cytotoxic Evaluation, and SAR of Epoxysterols

  摘要：

  A library of diastereomerically pure epoxysterols, prepared by combining chemical and enzymatic methodologies, was evaluated for cytotoxicity toward human cancer and noncancer cell lines. Unsaturated steroids were oxidized by magnesium bis(monoperoxyphthal ate) hexahydrate in acetonitrile, and the resulting epimeric epoxides were enzymatically separated using Novozym 435 or lipase AY. Some of the synthesized epoxysterols have potent cytotoxicity and higher activity on cancer cell lines HT29 and LAMA-84.

  DOI：

  10.1021/jm9003973

文献信息

• Efficient Chemoenzymatic Synthesis, Cytotoxic Evaluation, and SAR of Epoxysterols
  作者：João F. S. Carvalho、M. Manuel Cruz Silva、João N. Moreira、Sérgio Simões、M. Luisa Sá e Melo

  DOI：10.1021/jm9003973

  日期：2009.7.9

  A library of diastereomerically pure epoxysterols, prepared by combining chemical and enzymatic methodologies, was evaluated for cytotoxicity toward human cancer and noncancer cell lines. Unsaturated steroids were oxidized by magnesium bis(monoperoxyphthal ate) hexahydrate in acetonitrile, and the resulting epimeric epoxides were enzymatically separated using Novozym 435 or lipase AY. Some of the synthesized epoxysterols have potent cytotoxicity and higher activity on cancer cell lines HT29 and LAMA-84.