6β-hydroxysinomenine | 478064-44-7

• 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: 6β-hydroxysinomenine
• 英文别名: ent-3,7-dimethoxy-17-methyl-morphin-7-ene-4,6α-diol；ent-3,7-Dimethoxy-17-methyl-morphin-7-en-4,6α-diol；β-hydroxy-sinomenine；Sinomeninol-B
• CAS: 478064-44-7
• 化学式: C₁₉H₂₅NO₄
• 分子量: 331.412
• InChiKey: KKXRIHVJLRZHGU-UMCXVIDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  62.16
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6β-hydroxysinomenine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 6β-hydroxy-7,8-dihydrosinomenine
  参考文献：
  名称：

  Synthesis, characterization, and NF-κB pathway inhibition of 1-halogenated sinomenine derivatives

  摘要：

  设计并合成了一系列1-卤代紫草素衍生物。所有合成的衍生物均通过ESI-MS和PMR进行了结构确认。在体外评估了衍生物对NF-κB通路的抑制作用，使用了pNF-κB-luc细胞系。衍生物5b、6a、6c和7a的NF-κB活性抑制效果，其IC50值低于紫草素。

  DOI：

  10.1007/s10600-013-0457-8
• 作为产物：
  描述：

  青藤碱 在 四氢呋喃 、 lithium aluminium tetrahydride 作用下， 生成 6β-hydroxysinomenine
  参考文献：
  名称：

  Liquid–liquid phase separation and crystallization behavior of poly(ethylene terephthalate)/poly(ether imide) blend

  摘要：

  The liquid-liquid (L-L) phase separation and crystallization behavior of poly(ethylene terephthalate) (PET)/poly(ether imide) (PEI) blend were investigated with optical microscopy, light scattering, and small angle X-ray scattering (SAXS). The thermal analysis showed that the concentration fluctuation between separated phases was controllable by changing the time spent for demixing before crystallization. The L-L phase-separated specimens at 130 C for various time periods were subjected to a temperature-jump of 180 C for the isothermal crystallization and then effects of L-L phase separation on crystallization were investigated. The crystal growth rate decreased with increasing L-L phase-separated time (t(s)). The slow crystallization for a long t(s) implied that the growth path of crystals was highly distorted by the rearrangement of the spinodal domains associated with coarsening. The characteristic morphological parameters at the lamellar level were determined by the correlation function analysis on the SAXS data. The blend had a larger amorphous layer thickness than the pure PET, indicating that PEI molecules in the PET-rich phase were incorporated into the interlamellar regions during crystallization. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0032-3861(02)00054-x

文献信息

• Synthesis and Anti-Inflammatory Effect of Sinomenine 4-Hydroxy Esters
  作者：Dan Wang、Rong Zhang、Chunbao Jiang、Aun Raza、Jian Tang、Zhen Ouyang、Zhaoliang Su、Huaxi Xu

  DOI：10.1007/s10600-018-2275-5

  日期：2018.1

  In order to find more active anti-neuroinflammatory sinomenine derivatives, 17 sinomenine 4-hydroxy esters were designed and prepared. All synthesized derivatives were structurally confirmed by ESI-MS and PMR. Their anti-neuroinflammatory effects were evaluated using LPS-stimulated BV-2 microglia cells. Among them, four compounds presented more than 80% of cell viability. Compound 8 showed remarkable

  为了寻找更具活性的抗神经炎症的青藤碱衍生物，设计并制备了17种青藤碱4-羟基酯。所有合成的衍生物均通过 ESI-MS 和 PMR 进行结构确认。使用 LPS 刺激的 BV-2 小胶质细胞评估它们的抗神经炎症作用。其中，四种化合物呈现超过 80% 的细胞活力。通过 Griess 方法，化合物 8 显示出对一氧化氮 (NO) 释放的显着抑制。此外，测试了酯 5-9 以检查它们对二甲苯引起的耳水肿的抑制作用。据观察，8 比具有较短脂肪链的 5-7 更具活性且毒性更小。
• Process for the Preparation of 6-Beta Hydroxy Morphinan Compounds
  申请人：Bao Jian

  公开号：US20090312552A1

  公开（公告）日：2009-12-17

  The invention provides processes for the conversion of a 6-keto morphinan to a 6-hydroxy morphinan. In particular, the invention provides a stereoselective process for the conversion of a 6-keto morphinan to a 6-beta-hydroxy morphinan.

  该发明提供了将6-酮吗啡烷转化为6-羟基吗啡烷的过程。具体地，该发明提供了一种立体选择性的过程，用于将6-酮吗啡烷转化为6-β-羟基吗啡烷。
• Goto; Yamamoto, Journal of the Agricultural Chemical Society of Japan, 1955, vol. 19, p. 110,119
  作者：Goto、Yamamoto

  DOI：——

  日期：——