methyl (4R)-4-[(1S,2R,4R,6S,8S,11S,12S,15R,16R)-2,16-dimethyl-9-oxo-5-oxapentacyclo[9.7.0.02,8.04,6.012,16]octadecan-15-yl]pentanoate | 1461716-24-4

• 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: methyl (4R)-4-[(1S,2R,4R,6S,8S,11S,12S,15R,16R)-2,16-dimethyl-9-oxo-5-oxapentacyclo[9.7.0.02,8.04,6.012,16]octadecan-15-yl]pentanoate
• CAS: 1461716-24-4
• 化学式: C₂₅H₃₈O₄
• 分子量: 402.574
• InChiKey: FHWDROKFWHSNMT-LTHZOOPKSA-N

物化性质

• 沸点：
  491.9±20.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  55.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (4R)-4-[(1S,2R,4R,6S,8S,11S,12S,15R,16R)-2,16-dimethyl-9-oxo-5-oxapentacyclo[9.7.0.02,8.04,6.012,16]octadecan-15-yl]pentanoate 在 Selectfluor 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 methyl (4R)-4-[(1S,2R,4R,6S,8S,10S,11S,12S,15R,16R)-10-fluoro-2,16-dimethyl-9-oxo-5-oxapentacyclo[9.7.0.02,8.04,6.012,16]octadecan-15-yl]pentanoate
  参考文献：
  名称：

  Synthesis of 5α-cholestan-6-one derivatives and their inhibitory activities of NO production in activated microglia: Discovery of a novel neuroinflammation inhibitor

  摘要：

  Glial activation-mediated neuroinflammation plays a pivotal role in the process of several neuroinflammatory diseases including stroke, Alzheimer's diseases, Parkinson's diseases, multiple sclerosis and ischemia. Inhibition of microglial activation may ameliorate neuronal degeneration under the inflammatory conditions. In the present study, a number of 5 alpha-cholestan-6-one derivatives were prepared and the anti-inflammatory effects of these compounds were evaluated in LPS-stimulated BV-2 microglia cells. Those derivatives were synthesized from readily available hyodeoxycholic acid (1). Among the tested compounds, several analogs (16-18, 25, 35, 38) exhibited potent inhibitory activities on nitric oxide production with no or weak cell toxicity. Compound 16 also significantly suppressed the expression of TNF-alpha, interleukin (IL)-1 beta, cyclooxygenase (COX-2) as well as inducible nitric oxide synthase (iNOS) in LPS-stimulated BV-2 microglia cells. In addition, compound 16 markedly reduced infarction volume in a focal ischemic mice model. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.055
• 作为产物：
  描述：

  猪去氧胆酸 在 盐酸 、 重铬酸吡啶 、 silica gel 、 copper(II) sulfate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 四氯乙烯 、 二氯甲烷 、 水 为溶剂， 生成 methyl (4R)-4-[(1S,2R,4R,6S,8S,11S,12S,15R,16R)-2,16-dimethyl-9-oxo-5-oxapentacyclo[9.7.0.02,8.04,6.012,16]octadecan-15-yl]pentanoate
  参考文献：
  名称：

  Synthesis of 5α-cholestan-6-one derivatives and their inhibitory activities of NO production in activated microglia: Discovery of a novel neuroinflammation inhibitor

  摘要：

  Glial activation-mediated neuroinflammation plays a pivotal role in the process of several neuroinflammatory diseases including stroke, Alzheimer's diseases, Parkinson's diseases, multiple sclerosis and ischemia. Inhibition of microglial activation may ameliorate neuronal degeneration under the inflammatory conditions. In the present study, a number of 5 alpha-cholestan-6-one derivatives were prepared and the anti-inflammatory effects of these compounds were evaluated in LPS-stimulated BV-2 microglia cells. Those derivatives were synthesized from readily available hyodeoxycholic acid (1). Among the tested compounds, several analogs (16-18, 25, 35, 38) exhibited potent inhibitory activities on nitric oxide production with no or weak cell toxicity. Compound 16 also significantly suppressed the expression of TNF-alpha, interleukin (IL)-1 beta, cyclooxygenase (COX-2) as well as inducible nitric oxide synthase (iNOS) in LPS-stimulated BV-2 microglia cells. In addition, compound 16 markedly reduced infarction volume in a focal ischemic mice model. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.055

文献信息

• Synthesis of 5α-cholestan-6-one derivatives and their inhibitory activities of NO production in activated microglia: Discovery of a novel neuroinflammation inhibitor
  作者：Ya-Xi Yang、Long-Tai Zheng、Jing-Jing Shi、Bo Gao、Yan-Ke Chen、Hui-Chi Yang、Hong-Li Chen、Yuan-Chao Li、Xue-Chu Zhen

  DOI：10.1016/j.bmcl.2013.12.055

  日期：2014.2

  Glial activation-mediated neuroinflammation plays a pivotal role in the process of several neuroinflammatory diseases including stroke, Alzheimer's diseases, Parkinson's diseases, multiple sclerosis and ischemia. Inhibition of microglial activation may ameliorate neuronal degeneration under the inflammatory conditions. In the present study, a number of 5 alpha-cholestan-6-one derivatives were prepared and the anti-inflammatory effects of these compounds were evaluated in LPS-stimulated BV-2 microglia cells. Those derivatives were synthesized from readily available hyodeoxycholic acid (1). Among the tested compounds, several analogs (16-18, 25, 35, 38) exhibited potent inhibitory activities on nitric oxide production with no or weak cell toxicity. Compound 16 also significantly suppressed the expression of TNF-alpha, interleukin (IL)-1 beta, cyclooxygenase (COX-2) as well as inducible nitric oxide synthase (iNOS) in LPS-stimulated BV-2 microglia cells. In addition, compound 16 markedly reduced infarction volume in a focal ischemic mice model. (C) 2013 Elsevier Ltd. All rights reserved.