(E)-2,2'-di(2-carbomethoxy)cyanovinyl-4',5'-methylenedioxy-4,5,6-trimethoxybiphenyl | 1526944-22-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-2,2'-di(2-carbomethoxy)cyanovinyl-4',5'-methylenedioxy-4,5,6-trimethoxybiphenyl
• 英文别名: ethyl (E)-2-cyano-3-[6-[6-[(E)-2-cyano-3-ethoxy-3-oxoprop-1-enyl]-2,3,4-trimethoxyphenyl]-1,3-benzodioxol-5-yl]prop-2-enoate
• CAS: 1526944-22-8
• 化学式: C₂₈H₂₆N₂O₉
• 分子量: 534.522
• InChiKey: OKNFIFVOQUYPGK-GCBPPVMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  146
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  6-formyl-2,3,4-trimethoxyphenylboronic acid 在 哌啶 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 caesium carbonate 、 溶剂黄146 作用下， 以 乙二醇二甲醚 为溶剂， 生成 (E)-2,2'-di(2-carbomethoxy)cyanovinyl-4',5'-methylenedioxy-4,5,6-trimethoxybiphenyl
  参考文献：
  名称：

  Discovery of novel antitumor dibenzocyclooctatetraene derivatives and related biphenyls as potent inhibitors of NF-κB signaling pathway

  摘要：

  Several dibenzocyclooctatetraene derivatives (5-7) and related biphenyls (8-11) were designed, synthesized, and evaluated for inhibition of cancer cell growth and the NF-kappa B signaling pathway. Compound 5a, a dibenzocyclooctatetraene succinimide, was discovered as a potent inhibitor of the NF-kappa B signaling pathway with significant antitumor activity against several human tumor cell lines (GI(50) 1.38-1.45 mu M) and was more potent than paclitaxel against the drug-resistant KBvin cell line. Compound 5a also inhibited LPS-induced NF-kappa B activation in RAW264.7 cells with an IC50 value of 0.52 mu M, prevented I kappa B-alpha degradation and p65 nuclear translocation, and suppressed LPS-induced NO production in a dose-dependent manner. The antitumor data in cellular assays indicated that relative positions and types of substituents on the dibenzocyclooctatetraene or acyclic biphenyl as well as torsional angles between the two phenyls are of primary importance to antitumor activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.018

文献信息

• Discovery of novel antitumor dibenzocyclooctatetraene derivatives and related biphenyls as potent inhibitors of NF-κB signaling pathway
  作者：Fang-Lin Yu、Xiao-Yang He、Chunping Gu、Emika Ohkoshi、Li-Ting Wang、Sheng-Biao Wang、Chin-Yu Lai、Le Yu、Susan L. Morris-Natschke、Kuo-Hsiung Lee、Shuwen Liu、Lan Xie

  DOI：10.1016/j.bmc.2013.11.018

  日期：2014.1

  Several dibenzocyclooctatetraene derivatives (5-7) and related biphenyls (8-11) were designed, synthesized, and evaluated for inhibition of cancer cell growth and the NF-kappa B signaling pathway. Compound 5a, a dibenzocyclooctatetraene succinimide, was discovered as a potent inhibitor of the NF-kappa B signaling pathway with significant antitumor activity against several human tumor cell lines (GI(50) 1.38-1.45 mu M) and was more potent than paclitaxel against the drug-resistant KBvin cell line. Compound 5a also inhibited LPS-induced NF-kappa B activation in RAW264.7 cells with an IC50 value of 0.52 mu M, prevented I kappa B-alpha degradation and p65 nuclear translocation, and suppressed LPS-induced NO production in a dose-dependent manner. The antitumor data in cellular assays indicated that relative positions and types of substituents on the dibenzocyclooctatetraene or acyclic biphenyl as well as torsional angles between the two phenyls are of primary importance to antitumor activity. (C) 2013 Elsevier Ltd. All rights reserved.