2-ethyl-3,4-dimethoxybenzaldehyde | 104216-94-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-ethyl-3,4-dimethoxybenzaldehyde
• 英文别名: 2-Aethyl-3,4-dimethoxy-benzaldehyd；Athylveratrumaldehyd
• CAS: 104216-94-6
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: UXBOWXBFESGOCH-UHFFFAOYSA-N

物化性质

• 沸点：
  145-148 °C(Press: 5 Torr)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-甲氧基苯基磷酸二乙酯 、 2-ethyl-3,4-dimethoxybenzaldehyde 在 18-冠醚-6 、 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.08h， 生成 (E)-2-ethyl-3,4,4'-trimethoxystilbene
  参考文献：
  名称：

  Substituted trans-Stilbenes, Including Analogues of the Natural Product Resveratrol, Inhibit the Human Tumor Necrosis Factor Alpha-Induced Activation of Transcription Factor Nuclear Factor KappaB

  摘要：

  The transcription factor nuclear factor kappaB (NF-kappa B), which regulates expression of numerous antiinflammatory genes as well as genes that promote development of the prosurvival, antiapoptotic state is up-regulated in many cancer cells. The natural product resveratrol, a polyphenolic trans-stilbene, has numerous biological activities and is a known inhibitor of activation of NF-kappa B, which may account for some of its biological activities. Resveratrol exhibits activity against a wide variety of cancer cells and has demonstrated activity as a cancer chemopreventive against all stages, i.e., initiation, promotion, and progression. The biological activities of resveratrol are often ascribed to its antioxidant activity. Both antioxidant activity and biological activities of analogues of resveratrol depend upon the number and location of the hydroxy groups. In the present study, phenolic analogues of resveratrol and a series of substituted trans-stilbenes without hydroxy groups were compared with resveratrol for their abilities to inhibit the human tumor necrosis factor alpha-induced (TNF-alpha) activation of NF-kappa B, using the Panomics NF-kappa B stable reporter cell line 293/NF-kappa B-luc. A series of 75 compounds was screened to identify substituted trans-stilbenes that were more active than resveratrol. Dose-response studies of the most active compounds were carried out to obtain IC50 values. Numerous compounds were identified that were more active than resveratrol, including compounds that were devoid of hydroxy groups and were 100-fold more potent than resveratrol. The substituted trans-stilbenes that were potent inhibitors of the activation of NF-kappa B generally did not exhibit antioxidant activity. The results from screening were confirmed using BV-2 microglial cells where resveratrol and analogues were shown to inhibit LPS-induced COX-2 expression.

  DOI：

  10.1021/jm060630x
• 作为产物：
  描述：

  在 盐酸 作用下， 以 四氢呋喃 为溶剂， 生成 2-ethyl-3,4-dimethoxybenzaldehyde
  参考文献：
  名称：

  Effect of the Substitution Pattern on Reactions of Methoxylated Araldehyde 2,4-Dimethylpent-3-ylimines with Organolithium Reagents

  摘要：

  DOI：

  10.1021/jo9602175

文献信息

• Aryl-substituted cycloalkanes and cycloalkenes and herbicidal use thereof
  申请人：ROHM AND HAAS COMPANY

  公开号：EP0768298A1

  公开（公告）日：1997-04-16

  Disclosed are herbicidal aryl substituted cycloalkyl and aryl substituted cycloalkenyl compounds, herbicidal compositions, and herbicidal use of the compounds and compositions. The aryl substituent is selected from substituted phenyl, unsubstituted or substituted five-membered heterocycle, and unsubstituted or substituted six-membered heterocycle.

  公开了具有除草作用的芳基取代环烷基和芳基取代环烯基化合物、除草组合物以及这些化合物和组合物的除草用途。芳基取代基选自取代苯基、未取代或取代的五元杂环和未取代或取代的六元杂环。
• Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin
  作者：Lorraine M. Deck、Lucy A. Hunsaker、Thomas A. Vander Jagt、Lisa J. Whalen、Robert E. Royer、David L. Vander Jagt

  DOI：10.1016/j.ejmech.2017.11.048

  日期：2018.1

  Inflammation and oxidative stress are common in many chronic diseases. Targeting signaling pathways that contribute to these conditions may have therapeutic potential. The transcription factor Nrf2 is a major regulator of phase II detoxification and anti-oxidant genes as well as anti-inflammatory and neuroprotective genes. Nrf2 is widespread in the CNS and is recognized as an important regulator of brain inflammation. The natural product curcumin exhibits numerous biological activities including ability, to induce the expression of Nrf2-dependent phase II and anti-oxidant enzymes. Curcumin has been examined in a number of clinical studies with limited success, mainly owing to limited bioavailability and rapid metabolism. Enone analogues of curcumin were examined with an Nrf2 reporter assay to identify Nrf2 activators. Analogues were separated into groups with a 7-carbon dienone spacer, as found in curcumin; a 5-carbon enone spacer with and without a ring; and a 3-carbon enone spacer. Activators of Nrf2 were found in all three groups, many of which were more active than curcumin. Dose response studies demonstrated that a range of substituents on the aromatic rings of these enones influenced not only the sensitivity to activation, reflected in EC50 values, but also the extent of activation, which suggests that multiple mechanisms are involved in the activation of Nrf2 by these analogues. (C) 2017 Published by Elsevier Masson SAS.
• Kaiser; Burger, Journal of the American Chemical Society, 1957, vol. 79, p. 4365,4369
  作者：Kaiser、Burger

  DOI：——

  日期：——
• US5866513A
  申请人：——

  公开号：US5866513A

  公开（公告）日：1999-02-02