2,3-Bis[(3,4,5-trimethoxyphenyl)methylidene]butanedioic acid | 120349-90-8

• 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: 2,3-Bis[(3,4,5-trimethoxyphenyl)methylidene]butanedioic acid
• 英文别名: 2,3-bis[(3,4,5-trimethoxyphenyl)methylidene]butanedioic acid
• CAS: 120349-90-8
• 化学式: C₂₄H₂₆O₁₀
• 分子量: 474.464
• InChiKey: XVERYTIQHRIOOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  硫酸二乙酯 、 2,3-Bis[(3,4,5-trimethoxyphenyl)methylidene]butanedioic acid 在 potassium carbonate 作用下， 以 二甲基亚砜 、 丙酮 为溶剂， 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
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 丁二酸二乙酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 2,3-Bis[(3,4,5-trimethoxyphenyl)methylidene]butanedioic acid
  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