(1E,4Z,6E)-5-hydroxy-1,7-bis(2,4,6-trimethoxyphenyl)hepta-1,4,6-trien-3-one | 1400942-76-8

• 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)-5-hydroxy-1,7-bis(2,4,6-trimethoxyphenyl)hepta-1,4,6-trien-3-one
• CAS: 1400942-76-8
• 化学式: C₂₅H₂₈O₈
• 分子量: 456.493
• InChiKey: HAHQCHOIJVSXKO-OTUZTYJSSA-N

物化性质

• 熔点：
  187-190 °C
• 沸点：
  674.9±55.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-溴香兰素 、 (1E,4Z,6E)-5-hydroxy-1,7-bis(2,4,6-trimethoxyphenyl)hepta-1,4,6-trien-3-one 在 吡啶 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以76.57%的产率得到(1E,6E)-4-(3-bromo-4-hydroxy-5-methoxybenzylidene)-1,7-bis(2,4,6-trimethoxyphenyl)hepta-1,6-diene-3,5-dione
  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
• 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)-5-hydroxy-1,7-bis(2,4,6-trimethoxyphenyl)hepta-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

• Synthesis, electrochemical and photophysical studies of the borondifluoride complex of a meta-linked biscurcuminoid
  作者：Morgane Rivoal、Elena Zaborova、Gabriel Canard、Anthony D'Aléo、Frédéric Fages

  DOI：10.1039/c5nj00925a

  日期：——

  One- and two-photon absorption by the borondifluoride complex of a meta-linked biscurcuminoid provides NIR fluorescence emission with high brightnesses in the solid state.

  通过一个和两个光子吸收，一个meta-连接的双姜黄素的硼二氟化物复合物在固态中提供具有高亮度的近红外荧光发射。
• Curcuminoid-inspired synthetic compounds as anti-tumor agents
  申请人：Laali Kenneth K.

  公开号：US10934241B2

  公开（公告）日：2021-03-02

  Novel CUR— and CUR—BF2 compounds exhibiting anti-tumor properties are presented. CUR compounds bearing fluorinated moieties with selective fluorine introduction into the α-carbonyl moiety as well as CUR—BF2 adducts and CURs with diverse substitution patterns in the phenyl rings including fluorinated substituents (SCF3, OCF3, and F) and/or bulky activating groups (OMe, OAc, and OBz) are presented. Fluorinated aryl-pyrazoles and isoxazoles as well as novel CUR and CUR—BF2 compounds with monocyclic aromatic and bicyclic-heteroaromatic lateral rings, bearing fluorine(s), OCF3, CF3, and SCF3 groups, and their alpha-carbonyl-fluorinated analogs, as well as their pyrazole and isoxazole derivatives are presented. The CUR-pyrazoles embody analogs that are fluorinated at the phenyl-pyrazole moiety. The compounds and their derivatives exhibited exceptional cytotoxic and anti-proliferative activity against several cancer cell-lines. Deuterated CUR—BF2 and CUR compounds were also synthesized.

  本文介绍了具有抗肿瘤特性的新型 CUR 和 CUR-BF2 化合物。介绍了在 α-羰基中选择性引入氟的含氟 CUR 化合物，以及 CUR-BF2 加合物和在苯环中具有不同取代模式的 CUR，包括含氟取代基（SCF3、OCF3 和 F）和/或大块活化基团（OMe、OAc 和 OBz）。介绍了含氟芳基吡唑和异噁唑，以及带有氟、OCF3、CF3 和 SCF3 基团的单环芳香族和双环异芳香族侧环的新型 CUR 和 CUR-BF2 化合物及其α-羰基氟化类似物，以及它们的吡唑和异噁唑衍生物。CUR 吡唑包含在苯基吡唑分子上氟化的类似物。这些化合物及其衍生物对几种癌细胞系具有卓越的细胞毒性和抗增殖活性。此外，还合成了氚代 CUR-BF2 和 CUR 化合物。
• NOVEL CURCUMINOID-INSPIRED SYNTHETIC COMPOUNDS AS ANTI-TUMOR AGENTS
  申请人：Laali Kenneth K.

  公开号：US20210087208A1

  公开（公告）日：2021-03-25

  Novel CUR- and CUR-BF 2 compounds as well as novel bis and mono-NSAID/CUR-BF 2 and NSAID/CUR hybrids exhibiting anti-tumor properties are presented. CUR compounds bearing fluorinated moieties with selective fluorine introduction into the α-carbonyl moiety as well as CUR-BF 2 adducts and CURs with diverse substitution patterns in the phenyl rings including fluorinated substituents (SCF 3 , OCF 3 , and F) and/or bulky activating groups (OMe, OAc, and OBz) are presented. Fluorinated aryl-pyrazoles and isoxazoles as well as novel CUR and CUR-BF 2 compounds with monocyclic aromatic and bicyclic-heteroaromatic lateral rings, bearing fluorine(s), OCF 3 , CF 3 , and SCF 3 groups, and their alpha-carbonyl-fluorinated analogs, as well as their pyrazole and isoxazole derivatives are presented. The CUR-pyrazoles embody analogs that are fluorinated at the phenyl-pyrazole moiety. The hybrids, compounds, and their derivatives exhibited exceptional cytotoxic and anti-proliferative activity against several cancer cell-lines. The hybrid NSAID/CUR compounds also exhibited exceptional anti-inflammatory activity over NSAID or curcumin alone.
• 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.