eulophiol

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: eulophiol
• 英文别名: 2,7-dimethoxy-9,10-dihydrophenanthrene-1,5-diol
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: XCGSVZJXMLVULN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 eulophiol 以 吡啶 为溶剂， 反应 24.0h， 生成 eulophiol diacetate
  参考文献：
  名称：

  来自 Eulophia nuda 块茎的 9,10-二氢菲

  摘要：

  摘要 从 Eulophia nuda 的块茎中分离出一种结晶的 9,10-二氢菲，命名为 eulophiaol。经 1 H 和 13 CNMR 鉴定为 1,5-二羟基-2,7-二甲氧基-9,10-二氢菲。

  DOI：

  10.1016/s0031-9422(00)86975-7
• 作为产物：
  描述：

  2-苄氧基-3-甲氧基苯甲醛 在 sodium tetrahydroborate 、 偶氮二异丁腈 、 palladium 10% on activated carbon 、 lithium methanolate 、 氢气 、 三正丁基氢锡 、 三溴化磷 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 异丙醇 、 甲苯 为溶剂， 220.0 ℃ 、482.64 kPa 条件下， 反应 36.0h， 生成 eulophiol
  参考文献：
  名称：

  Regioselective synthesis of phenanthrenes and evaluation of their anti-oxidant based anti-inflammatory potential

  摘要：

  Regioselective synthesis of 9,10-Dihydro-2,5-Dimethoxyphenanthrene-1,7-diol (1) and 9,10-Dihydro-2,7-Dimethoxyphenanthrene-1,5-diol (2) was achieved using regioselective methylation, Wittig reaction, intramolecular cyclization and hydrogenation as key steps. The synthesis was successfully completed in total of 15 steps with 3.3% overall yield in case of 1 and in total of 13 steps with 9.0% overall yield in case of 2. All compounds (1-4) showed good antioxidant and anti-inflammatory activity in in vitro assays and these activities were found to be due the presence of phenolic hydroxyl groups. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.016

文献信息

• TOLL LIKE RECEPTOR (TLR) SIGNALING ANTAGONIST
  申请人：Upadhyay Shakti

  公开号：US20090215908A1

  公开（公告）日：2009-08-27

  The present invention relates to novel synthetic toll like receptor antagonist. The present invention in particular provides compounds, methods and compositions for specifically inhibiting immune stimulation involving TLR ligands, especially TLR-4. The compounds are potentially useful in treatment of inflammation, autoimmunity, allergy, asthma, graft rejection, graft versus host disease, infection, sepsis, cancer and immunodeficiency.

  本发明涉及新型合成的Toll样受体拮抗剂。本发明特别提供了一种针对TLR配体特异性抑制免疫刺激的化合物、方法和组合物，尤其是针对TLR-4。这些化合物在治疗炎症、自身免疫、过敏、哮喘、移植排斥、移植物抗宿主病、感染、败血症、癌症和免疫缺陷方面具有潜在的用途。
• [EN] TOLL LIKE RECEPTOR (TLR) SIGNALING ANTAGONIST<br/>[FR] ANATAGONISTE DE SIGNALISATION DE RÉCEPTEURS DE TYPE TOLL (TLR)
  申请人：RELIANCE LIFE SCIENCES PVT LTD

  公开号：WO2009047791A2

  公开（公告）日：2009-04-16

  The present invention relates to novel synthetic toll like receptor antagonist. The present invention in particular provides compounds, methods and compositions for specifically inhibiting immune stimulation involving TLR ligands, especially TLR-4. The compounds are potentially useful in treatment of inflammation, autoimmunity, allergy, asthma, graft rejection, graft versus host disease, infection, sepsis, cancer and immunodeficiency.
• Regioselective synthesis of phenanthrenes and evaluation of their anti-oxidant based anti-inflammatory potential
  作者：Yogesh Kanekar、Khalander Basha、Sharad Duche、Rajan Gupte、Arnab Kapat

  DOI：10.1016/j.ejmech.2013.06.016

  日期：2013.9

  Regioselective synthesis of 9,10-Dihydro-2,5-Dimethoxyphenanthrene-1,7-diol (1) and 9,10-Dihydro-2,7-Dimethoxyphenanthrene-1,5-diol (2) was achieved using regioselective methylation, Wittig reaction, intramolecular cyclization and hydrogenation as key steps. The synthesis was successfully completed in total of 15 steps with 3.3% overall yield in case of 1 and in total of 13 steps with 9.0% overall yield in case of 2. All compounds (1-4) showed good antioxidant and anti-inflammatory activity in in vitro assays and these activities were found to be due the presence of phenolic hydroxyl groups. (C) 2013 Elsevier Masson SAS. All rights reserved.
• A 9,10-dihydrophenanthrene from tubers of Eulophia nuda
  作者：S.R. Bhandari、A.H. Kapadi

  DOI：10.1016/s0031-9422(00)86975-7

  日期：1983.1

  Abstract A crystalline 9,10-dihydrophenanthrene, named eulophiol, has been isolated from the tubers of Eulophia nuda . It was identified as 1,5-dihydroxy-2,7-dimethoxy-9,10-dihydrophenanthrene by 1 H and 13 CNMR.

  摘要 从 Eulophia nuda 的块茎中分离出一种结晶的 9,10-二氢菲，命名为 eulophiaol。经 1 H 和 13 CNMR 鉴定为 1,5-二羟基-2,7-二甲氧基-9,10-二氢菲。