4-O-ethylsinomenine | 1246560-80-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 吗啡烷
• 英文名称: 4-O-ethylsinomenine
• 英文别名: 4-Ethyl-Sinomenine；(1R,9S,10S)-3-ethoxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,11-tetraen-13-one
• CAS: 1246560-80-4
• 化学式: C₂₁H₂₇NO₄
• 分子量: 357.45
• InChiKey: CQCLKYWTMILTBY-LRAJWGHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-O-ethylsinomenine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.42h， 以96%的产率得到
  参考文献：
  名称：

  Highly Stereoselective Synthesis of Functionalised Sinomenine Derivatives by Reducing the C-6 (Ring C)

  摘要：

  C-4（环 A）上的西诺明醚衍生物被 C-6（环 C）上的 LiAlH4 还原，以高度的立体选择性提供相应的羟基衍生物。所需的产物产量极高，并通过 1H NMR、13C NMR、MS 光谱、元素分析和 X 射线衍射进行了全面表征。温和的反应条件、易于获得的 sinomenine 醚衍生物、简单的操作和高立体选择性使该反应极具吸引力。

  DOI：

  10.3184/174751914x14176845374506
• 作为产物：
  描述：

  乙醇 、 青藤碱 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 12.5h， 以99%的产率得到4-O-ethylsinomenine
  参考文献：
  名称：

  Synthesis and biological evaluation of novel sinomenine derivatives as anti-inflammatory agents

  摘要：

  Sinomenine (1) is clinically available for the treatment of rheumatoid arthritis (RA), however, its efficacy is quite weak. In the present study, a library of novel sinomenine-based homodimers and monomers through variable-length linkers were designed and synthesized, and their bioactivities were evaluated using RAW264.7 cells and mice. Among the compounds, 2f and 3b possessed much more potent inhibitory effects on the production of nitric oxide (NO), interleukin-6 (IL-6) and tumor necrosis factor-alpha (TNF-alpha) than 1. Preliminary mechanism investigation revealed that 3b inhibited nuclear factor-kappa B (NF-kappa B) signaling pathway specifically, 2f suppressed both NF-kappa B and mitogen-activated protein kinase (MAPK) cascades. Moreover, 3b and 2f significantly alleviated the lipopolysaccharide (LPS)-induced mortality. These two compounds might serve as valuable candidates for anti-inflammatory drug discovery. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.036

文献信息

• Synthesis and biological evaluation of novel sinomenine derivatives as anti-inflammatory agents
  作者：Peng Teng、Hai-Liang Liu、Lei Zhang、Li-Li Feng、Yue Huai、Zhang-Shuang Deng、Yang Sun、Qiang Xu、Jian-Xin Li

  DOI：10.1016/j.ejmech.2012.01.036

  日期：2012.4

  Sinomenine (1) is clinically available for the treatment of rheumatoid arthritis (RA), however, its efficacy is quite weak. In the present study, a library of novel sinomenine-based homodimers and monomers through variable-length linkers were designed and synthesized, and their bioactivities were evaluated using RAW264.7 cells and mice. Among the compounds, 2f and 3b possessed much more potent inhibitory effects on the production of nitric oxide (NO), interleukin-6 (IL-6) and tumor necrosis factor-alpha (TNF-alpha) than 1. Preliminary mechanism investigation revealed that 3b inhibited nuclear factor-kappa B (NF-kappa B) signaling pathway specifically, 2f suppressed both NF-kappa B and mitogen-activated protein kinase (MAPK) cascades. Moreover, 3b and 2f significantly alleviated the lipopolysaccharide (LPS)-induced mortality. These two compounds might serve as valuable candidates for anti-inflammatory drug discovery. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Highly Stereoselective Synthesis of Functionalised Sinomenine Derivatives by Reducing the C-6 (Ring C)
  作者：Xingliang Zheng、Weihua Zhu、Liqiong Han、Kecui Zhang、Tong Pan

  DOI：10.3184/174751914x14176845374506

  日期：2014.12

  Sinomenine ether derivatives at C-4 (ring A) were reduced by LiAlH₄ at the C-6 (ring C) to provide the corresponding hydroxyl derivatives with highly stereoselectivity. The desired products were obtained in excellent yields and fully characterised by ¹H NMR, ¹³C NMR, MS spectra, elemental analysis and X-ray diffraction. The mild reaction conditions, readily available sinomenine ether derivatives, simple operation and high stereoselectivity make such a reaction highly attractive.

  C-4（环 A）上的西诺明醚衍生物被 C-6（环 C）上的 LiAlH4 还原，以高度的立体选择性提供相应的羟基衍生物。所需的产物产量极高，并通过 1H NMR、13C NMR、MS 光谱、元素分析和 X 射线衍射进行了全面表征。温和的反应条件、易于获得的 sinomenine 醚衍生物、简单的操作和高立体选择性使该反应极具吸引力。