diethyl 2,3-bis[(3,4,5-trimethoxyphenyl)methylidene]butanedioate | 1562577-15-4

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: diethyl 2,3-bis[(3,4,5-trimethoxyphenyl)methylidene]butanedioate
• CAS: 1562577-15-4
• 化学式: C₂₈H₃₄O₁₀
• 分子量: 530.572
• InChiKey: QILPNPOEZOFVJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  38.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  107.98
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 在 sodium hydride 、 potassium carbonate 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 6.0h， 生成 diethyl 2,3-bis[(3,4,5-trimethoxyphenyl)methylidene]butanedioate
  参考文献：
  名称：

  Synthesis of neolignans as microtubule stabilisers

  摘要：

  Tubulin is a well established target for anticancer drug development. Lignans and neolignans were synthesized as tubulin interacting agents. Neolignans 10 and 19 exhibited significant anticancer activity against MCF-7 and MDAMB-231 human breast cancer cell lines. Both the compounds effectively induced stabilization of microtubule at 4 and 20 mu M concentrations respectively. Neolignan 10 induced G2/M phase arrest in MCF-7 cells. Docking experiments raveled that 10 and 19 occupied the same binding pocket of paclitaxel with some difference in active site amino acids and good bioavailability of both the compounds. In in vivo acute oral toxicity 10 was well tolerated up to 300 mg/kg dose in Swiss-albino mice. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.067

文献信息

• Biomimetic regioselective and high-yielding Cu(<scp>i</scp>)-catalyzed dimerization of sinapate esters in green solvent Cyrene™: towards sustainable antioxidant and anti-UV ingredients
  作者：Matthieu M. Mention、Amandine L. Flourat、Cédric Peyrot、Florent Allais

  DOI：10.1039/d0gc00122h

  日期：——

  work aimed at designing an industrially relevant sustainable synthetic pathway allowing their selective β–β′ dimerization to enhance their properties with a view to use them in commercial applications such as functional additives for cosmetics, plastics and food/feed. A copper(I)-catalyzed procedure involving pyridine and O2 from air was developed and greened up using the REACH-compliant bio-based

  天然的芥子酸及其酯是抗紫外线和抗自由基化学物质。这项工作旨在设计一种工业相关的可持续合成途径，使它们的选择性β-β'二聚化以增强其性能，以期将其用于商业用途，例如化妆品，塑料和食品/饲料的功能性添加剂。涉及吡啶和O 2的铜（I）催化过程使用符合REACH要求的生物基溶剂Cyrene™开发并绿色化空气。通过实验设计进一步优化后，这种可持续的合成工艺已成功应用于各种芥子酸酯，并已在多克规模上得到验证。相对于商业抗氧化剂，将所得的β-β'二棕榈酸酯的抗自由基活性进行了基准测试，而将其紫外线吸收率与植物中发现的天然抗紫外线化合物辛那普酰苹果酸和广泛使用的商业防晒成分Octinoxate™的抗紫外线活性进行了比较。 。结果表明，这些二聚体是更好的自由基清除剂，不仅表现出更好的紫外线吸收率，而且覆盖了UV-A和UV-B区域。
• Synthesis of neolignans as microtubule stabilisers
  作者：B. Sathish Kumar、Aastha Singh、Amit Kumar、Jyotsna Singh、Mohammad Hasanain、Arjun Singh、Nusrat Masood、Dharmendra K. Yadav、Rituraj Konwar、Kalyan Mitra、Jayanta Sarkar、Suaib Luqman、Anirban Pal、Feroz Khan、Debabrata Chanda、Arvind S. Negi

  DOI：10.1016/j.bmc.2013.12.067

  日期：2014.2

  Tubulin is a well established target for anticancer drug development. Lignans and neolignans were synthesized as tubulin interacting agents. Neolignans 10 and 19 exhibited significant anticancer activity against MCF-7 and MDAMB-231 human breast cancer cell lines. Both the compounds effectively induced stabilization of microtubule at 4 and 20 mu M concentrations respectively. Neolignan 10 induced G2/M phase arrest in MCF-7 cells. Docking experiments raveled that 10 and 19 occupied the same binding pocket of paclitaxel with some difference in active site amino acids and good bioavailability of both the compounds. In in vivo acute oral toxicity 10 was well tolerated up to 300 mg/kg dose in Swiss-albino mice. (C) 2014 Elsevier Ltd. All rights reserved.