2,3-bis(4-hydroxy-3-methoxybenzylidene)succinaldehyde | 24058-19-3

• 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(4-hydroxy-3-methoxybenzylidene)succinaldehyde
• 英文别名: (2E,3E)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methylidene]butanedial
• CAS: 24058-19-3
• 化学式: C₂₀H₁₈O₆
• 分子量: 354.359
• InChiKey: RGZIGIOCSACKAU-DUGOVBPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,5-二甲氧基四氢呋喃 、 香草醛 在 potassium acetate 、 溶剂黄146 作用下， 以 水 为溶剂， 以10%的产率得到2,3-bis(4-hydroxy-3-methoxybenzylidene)succinaldehyde
  参考文献：
  名称：

  Synthesis and biological evaluation of dimeric cinnamaldehydes as potent antitumor agents

  摘要：

  It has been reported that 2-hydroxycinnamaldehyde and 2-benzoyl-oxycinnamaldehyde inhibited the activity of farnesyl protein transferase, angiogenesis, cell-cell adhesion, and tumor growth in vivo model. In order to improve its anti-tumor activity., dimeric cinnainaldehydes have been synthesized based oil 2-hydroxycinnamaldehyde. The synthesized compounds strongly inhibited the growth of human colon tumor cells with GI(50) values of 0.6-10 mu M. Especially, 2-piperazine derivative blocked ill vivo growth of human colon tumor xenograft in nude mice at 10 mg/kg. It was found that their anti-tumor effects induce apoptosis and cell cycle arrest at G(2)/M phase by the compounds. It was confirmed by detection of apoptosis markers such as activated caspase-3 and cleaved PARP, and cell cycle analysis. The dimeric compounds also inhibited Cdc25B phosphatase which is essential for preinitiating G(2)/M transition and S phase progression. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.028

文献信息

• Cinnamaldehyde derivatives inhibiting growth of tumor cell and regulating cell cycle, preparations and pharmaceutical compositions thereof
  申请人：——

  公开号：US20040254196A1

  公开（公告）日：2004-12-16

  The present invention relates to cinnamaldehyde derivatives inhibiting growth of tumor cell and regulating cell cycle, the method for preparation and the pharmaceutical composition thereof. The cinnamaldehyde derivatives of the present invention can be effectively used as a cell cycle regulator or a cancer cell growth inhibitor, since it has an ability to regulate cell cycle by holding the cells in G2/M stage of the cell division and has activity to inhibit cancer cell growth.

  本发明涉及抑制肿瘤细胞生长和调节细胞周期的肉桂醛衍生物，以及其制备方法和药物组合物。本发明的肉桂醛衍生物可以有效地用作细胞周期调节剂或癌细胞生长抑制剂，因为它具有通过将细胞保持在细胞分裂的G2/M阶段来调节细胞周期，并具有抑制癌细胞生长的活性。
• NMR analysis of lignins in CAD-deficient plants. Part 1. Incorporation of hydroxycinnamaldehydes and hydroxybenzaldehydes into lignins
  作者：Hoon Kim、John Ralph、Fachuang Lu、Sally A. Ralph、Alain-M. Boudet、John J. MacKay、Ronald R. Sederoff、Takashi Ito、Shingo Kawai、Hideo Ohashi、Takayoshi Higuchi

  DOI：10.1039/b209686b

  日期：2003.1.13

  Peroxidase/H2O2-mediated radical coupling of 4-hydroxycinnamaldehydes produces 8–O–4-, 8–5-, and 8–8-coupled dehydrodimers as has been documented earlier, as well as the 5–5-coupled dehydrodimer. The 8–5-dehydrodimer is however produced kinetically in its cyclic phenylcoumaran form at neutral pH. Synthetic polymers produced from mixtures of hydroxycinnamaldehydes and normal monolignols provide the next level of complexity. Spectral data from dimers, oligomers, and synthetic polymers have allowed a more substantive assignment of aldehyde components in lignins isolated from a CAD-deficient pine mutant and an antisense-CAD-downregulated transgenic tobacco. CAD-deficient pine lignin shows enhanced levels of the typical benzaldehyde and cinnamaldehyde end-groups, along with evidence for two types of 8–O–4-coupled coniferaldehyde units. The CAD-downregulated tobacco also has higher levels of hydroxycinnamaldehyde and hydroxybenzaldehyde (mainly syringaldehyde) incorporation, but the analogous two types of 8–O–4-coupled products are the dominant features. 8–8-Coupled units are also clearly evident. There is clear evidence for coupling of hydroxycinnamaldehydes to each other and then incorporation into the lignin, as well as for the incorporation of hydroxycinnamaldehyde monomers into the growing lignin polymer. Coniferaldehyde and sinapaldehyde (as well as vanillin and syringaldehyde) co-polymerize with the traditional monolignols into lignins and do so at enhanced levels when CAD-deficiency has an impact on the normal monolignol production. The implication is that, particularly in angiosperms, the aldehydes behave like the traditional monolignols and should probably be regarded as authentic lignin monomers in normal and CAD-deficient plants.

  过氧化物酶/H2O2 介导的 4-羟基肉桂醛自由基偶联会产生 8-O-4-、8-5-和 8-8 偶联脱氢二聚体（如前所述）以及 5-5 偶联脱氢二聚体。不过，8-5-脱氢二聚体是在中性 pH 值下以环状苯基香豆素形式产生的。由羟基肉桂醛和正常单木质素混合物产生的合成聚合物提供了更高的复杂性。通过二聚体、低聚物和合成聚合物的光谱数据，我们可以对从 CAD 缺失的松树突变体和反义-CAD 下调的转基因烟草中分离出来的木质素中的醛组分进行更实质性的分配。CAD 缺失的松树木质素显示出典型的苯甲醛和肉桂醛末端基团含量增加，同时还显示出两种 8-O-4 偶联的松柏醛单元。CAD 下调的烟草也有较高水平的羟基肉桂醛和羟基苯甲醛（主要是丁香醛）掺入，但类似的两种 8-O-4 偶联产物是主要特征。8-8 偶联单元也很明显。有明显证据表明羟基肉桂醛相互偶联，然后掺入木质素中，以及羟基肉桂醛单体掺入生长中的木质素聚合物中。松柏醛和山奈醛（以及香兰素和丁香醛）与传统的单木质素共同聚合成木质素，当 CAD 缺乏影响到正常的单木质素生产时，它们的聚合水平会提高。这意味着，特别是在被子植物中，醛类的行为与传统的单木质素相似，在正常和 CAD 缺乏的植物中，醛类可能应被视为真正的木质素单体。
• US6949682B2
  申请人：——

  公开号：US6949682B2

  公开（公告）日：2005-09-27
• Synthesis and biological evaluation of dimeric cinnamaldehydes as potent antitumor agents
  作者：Dae-Seop Shin、Jong-Han Kim、Su-Kyung Lee、Dong Cho Han、Kwang-Hee Son、Hwan-Mook Kim、Hyae-Gyeong Cheon、Kwang-Rok Kim、Nack-Do Sung、Seung Jae Lee、Sung Kwon Kang、Byoung-Mog Kwon

  DOI：10.1016/j.bmc.2005.11.028

  日期：2006.4

  It has been reported that 2-hydroxycinnamaldehyde and 2-benzoyl-oxycinnamaldehyde inhibited the activity of farnesyl protein transferase, angiogenesis, cell-cell adhesion, and tumor growth in vivo model. In order to improve its anti-tumor activity., dimeric cinnainaldehydes have been synthesized based oil 2-hydroxycinnamaldehyde. The synthesized compounds strongly inhibited the growth of human colon tumor cells with GI(50) values of 0.6-10 mu M. Especially, 2-piperazine derivative blocked ill vivo growth of human colon tumor xenograft in nude mice at 10 mg/kg. It was found that their anti-tumor effects induce apoptosis and cell cycle arrest at G(2)/M phase by the compounds. It was confirmed by detection of apoptosis markers such as activated caspase-3 and cleaved PARP, and cell cycle analysis. The dimeric compounds also inhibited Cdc25B phosphatase which is essential for preinitiating G(2)/M transition and S phase progression. (c) 2005 Elsevier Ltd. All rights reserved.