(1E,4Z,6E)-1,7-bis(2,4-dimethoxyphenyl)-5-hydroxyhepta-1,4,6-trien-3-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (1E,4Z,6E)-1,7-bis(2,4-dimethoxyphenyl)-5-hydroxyhepta-1,4,6-trien-3-one
• 化学式: C₂₃H₂₄O₆
• 分子量: 396.44
• InChiKey: LUNNYEGTKIJRKO-AMJPCZIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1E,4Z,6E)-1,7-bis(2,4-dimethoxyphenyl)-5-hydroxyhepta-1,4,6-trien-3-one 在 二苯硫醚 、 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、137.9 kPa 条件下， 以85%的产率得到(Z)-1,7-bis(2,4-dimethoxyphenyl)-5-hydroxyhept-4-en-3-one
  参考文献：
  名称：

  天然多羟基类黄酮、姜黄素和合成姜黄素类似物作为 α7 nAChRs 正变构调节剂

  摘要：

  α7 烟碱乙酰胆碱受体 (α7 nAChR) 是一种配体门控离子通道，与认知障碍、精神分裂症、疼痛和炎症有关。与完全激动剂相比，这种受体的变构调节可能有利于降低毒性。我们之前用一些羟基查尔酮获得的结果，它们被鉴定为 α7 nAChR 的正变构调节剂 (PAM)，促使我们评估一些结构相关的天然黄酮类和姜黄素以及一些合成姜黄素类似物的潜力，目的是确定α7 nAChR 的新变构调节剂。生物学评估表明，根皮素、去甲氧基姜黄素和双去甲氧姜黄素表现为 α7 nAChR 的 PAM。此外，一些新的姜黄素衍生物能够增强乙酰胆碱诱发的信号；

  DOI：

  10.3390/ijms22020973
• 作为产物：
  描述：

  香草醛 在 boric anhydride 作用下， 以 乙酸乙酯 为溶剂， 反应 43.0h， 生成 (1E,4Z,6E)-1,7-bis(2,4-dimethoxyphenyl)-5-hydroxyhepta-1,4,6-trien-3-one
  参考文献：
  名称：

  Synthesis, cytotoxicity of new 4-arylidene curcumin analogues and their multi-functions in inhibition of both NF-κB and Akt signalling

  摘要：

  A series of new 4-arylidene curcumin analogues (4-arylidene-1,7-bisarylhepta-1,6-diene-3,5-diones) were synthesized and found to be potent antiproliferative agents against a panel of cancer cell lines at submicromolar to low micromolar concentrations by SRB assay. Their inhibitory abilities against NF-kappa B was evaluated by High Content Analysis (HCA) based immunofluorescence assay; and the Akt signalling inhibition was determined by fluorescence polarization assay and western blot respectively. The Structure Activity Relationship was discussed. Our results revealed that 4-arylidene curcumin analogues may work in a multi-targets manner in cancer cell. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.039

文献信息

• Antitumor Agents. 250. Design and Synthesis of New Curcumin Analogues as Potential Anti-Prostate Cancer Agents
  作者：Li Lin、Qian Shi、Alexander K. Nyarko、Kenneth F. Bastow、Chin-Chung Wu、Ching-Yuan Su、Charles C.-Y Shih、Kuo-Hsiung Lee

  DOI：10.1021/jm051043z

  日期：2006.6.1

  In a continuing study of curcumin analogues as potential drug candidates to treat prostate cancer at both androgen-dependent and androgen-refractory stages, we designed and synthesized over 40 new analogues classified into four series: monophenyl analogues ( series A), heterocycle-containing analogues ( series B), analogues bearing various substituents on the phenyl rings ( series C), and analogues with various linkers ( series D). These new compounds were tested for cytotoxicity against two human prostate cancer cell lines, androgen-dependent LNCaP and androgen-independent PC-3. Antiandrogenic activity was also evaluated in LNCaP cells and PC-3 cells transfected with wild-type androgen receptor. Ten compounds possessed potent cytotoxicity against both LNCaP and PC-3 cells, seven only against LNCaP, and one solely against PC-3. This study established an advanced structure-activity relationship ( SAR), and these correlations will guide the further design of new curcumin analogues with better anti-prostate cancer activity.
• Synthesis, cytotoxicity of new 4-arylidene curcumin analogues and their multi-functions in inhibition of both NF-κB and Akt signalling
  作者：Yinglin Zuo、Jianing Huang、Binhua Zhou、Shuni Wang、Weiyan Shao、Cuige Zhu、Li Lin、Gesi Wen、Hongyang Wang、Jun Du、Xianzhang Bu

  DOI：10.1016/j.ejmech.2012.07.039

  日期：2012.9

  A series of new 4-arylidene curcumin analogues (4-arylidene-1,7-bisarylhepta-1,6-diene-3,5-diones) were synthesized and found to be potent antiproliferative agents against a panel of cancer cell lines at submicromolar to low micromolar concentrations by SRB assay. Their inhibitory abilities against NF-kappa B was evaluated by High Content Analysis (HCA) based immunofluorescence assay; and the Akt signalling inhibition was determined by fluorescence polarization assay and western blot respectively. The Structure Activity Relationship was discussed. Our results revealed that 4-arylidene curcumin analogues may work in a multi-targets manner in cancer cell. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Natural Polyhydroxy Flavonoids, Curcuminoids, and Synthetic Curcumin Analogs as α7 nAChRs Positive Allosteric Modulators
  作者：Marta Ximenis、José Mulet、Salvador Sala、Francisco Sala、Manuel Criado、Rosario González-Muñiz、María Jesús Pérez de Vega

  DOI：10.3390/ijms22020973

  日期：——

  reduce the toxicity in comparison with full agonists. Our previous results obtained with some hydroxy-chalcones, which were identified as positive allosteric modulators (PAMs) of α7 nAChR, prompted us to evaluate the potential of some structurally related naturally occurring flavonoids and curcuminoids and some synthetic curcumin analogues, with the aim of identifying new allosteric modulators of the α7

  α7 烟碱乙酰胆碱受体 (α7 nAChR) 是一种配体门控离子通道，与认知障碍、精神分裂症、疼痛和炎症有关。与完全激动剂相比，这种受体的变构调节可能有利于降低毒性。我们之前用一些羟基查尔酮获得的结果，它们被鉴定为 α7 nAChR 的正变构调节剂 (PAM)，促使我们评估一些结构相关的天然黄酮类和姜黄素以及一些合成姜黄素类似物的潜力，目的是确定α7 nAChR 的新变构调节剂。生物学评估表明，根皮素、去甲氧基姜黄素和双去甲氧姜黄素表现为 α7 nAChR 的 PAM。此外，一些新的姜黄素衍生物能够增强乙酰胆碱诱发的信号；