2,6-bis(3,4-dihydroxybenzylidene)cyclohexanone | 142381-66-6

• 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: 2,6-bis(3,4-dihydroxybenzylidene)cyclohexanone
• 英文别名: 2,6-Bis(3,4-dihydroxybenzylidene) cyclohexanone；2,6-bis[(3,4-dihydroxyphenyl)methylidene]cyclohexan-1-one
• CAS: 142381-66-6
• 化学式: C₂₀H₁₈O₅
• 分子量: 338.36
• InChiKey: JZODVJPLOFJTJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-bis(3,4-dihydroxybenzylidene)cyclohexanone 、 乙酸酐 在 4-二甲氨基吡啶 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以91%的产率得到2,6-bis(3,4-diacetoxybenzylidene)cyclohexanone
  参考文献：
  名称：

  Synthesis and evaluation of DPPH and anti-inflammatory activities of 2,6-bisbenzylidenecyclohexanone and pyrazoline derivatives

  摘要：

  A series of thirty three 2,6-bisbenzylidenecyclohexanone and pyrazoline derivatives were synthesized and evaluated for inhibitory activities on IFN-gamma/LPS-activated RAW 264.7 cells and DPPH radical scavenging activity. Compounds 8, 9, and 11a demonstrated significant NO inhibitory activity as compared to L-NAME and curcumin with IC50 values of 6.68 +/- A 0.16, 6.09 +/- A 0.46, and 6.84 +/- A 0.12 mu M, respectively. Apparently the suppression upon NO secretion was not due to cell death since the active compounds did not reduce the cell viability in close proximity to the IC50 of NO inhibition. Overall, incorporation of pyrazoline ring as part of the linker chain improved cell viability compared to the 2,6-bisbenzylidenecyclohexanone derivatives. Meanwhile, compound 11 (IC50 = 13.27 +/- A 1.78 mu M) bearing ortho hydroxyls on the aromatic rings recorded the highest radical scavenging activity as compared with quercetin (IC50 = 21.46 +/- A 0.85 mu M).

  DOI：

  10.1007/s00044-010-9521-0
• 作为产物：
  描述：

  环己酮 、 3,4-二羟基苯甲醛 在 Montmorillonite K-10 作用下， 反应 0.08h， 生成 2,6-bis(3,4-dihydroxybenzylidene)cyclohexanone
  参考文献：
  名称：

  肉桂酰基衍生物作为p300组蛋白乙酰转移酶抑制剂的构效关系。

  摘要：

  人p300是一种多面体转录共激活因子，在乙酰化特定赖氨酸残基上的组蛋白乙酰化中起关键作用。大量证据表明，p300与多种疾病有关，包括白血病，肿瘤和病毒感染。它参与多效性生物学作用和与疾病的联系为确定其调制如何代表合适的药物靶标提供了理论依据。迄今为止，已经描述了几种p300抑制剂（即组蛋白乙酰转移酶抑制剂HATis），但是它们都具有效力低，缺乏特异性或细胞通透性低的缺点，因此突出了寻找更有效抑制剂的需求。我们的肉桂酰基衍生物2,6-双（3-溴-4-羟基亚苄基）环己酮（RC56）被鉴定为一种活性和选择性的p300抑制剂，并被证明是研究与p300的构效关系的良好候选物。在这里，我们描述与我们的命中结构相关的新HAT的设计，合成和生物学评估。此外，我们通过诱导拟合对接和分子动力学模拟的方法研究了p300与最佳命中分子之间的相互作用，从而深入了解了影响其对目标酶活性的独特化学特征。

  DOI：

  10.1002/cmdc.201700040

文献信息

• Synthesis and evaluation of DPPH and anti-inflammatory activities of 2,6-bisbenzylidenecyclohexanone and pyrazoline derivatives
  作者：Kok Wai Lam、Chau Ling Tham、Choi Yi Liew、Ahmad Syahida、Mohd. Basyaruddin Abdul Rahman、Daud A. Israf、Nordin H. Lajis

  DOI：10.1007/s00044-010-9521-0

  日期：2012.3

  A series of thirty three 2,6-bisbenzylidenecyclohexanone and pyrazoline derivatives were synthesized and evaluated for inhibitory activities on IFN-gamma/LPS-activated RAW 264.7 cells and DPPH radical scavenging activity. Compounds 8, 9, and 11a demonstrated significant NO inhibitory activity as compared to L-NAME and curcumin with IC50 values of 6.68 +/- A 0.16, 6.09 +/- A 0.46, and 6.84 +/- A 0.12 mu M, respectively. Apparently the suppression upon NO secretion was not due to cell death since the active compounds did not reduce the cell viability in close proximity to the IC50 of NO inhibition. Overall, incorporation of pyrazoline ring as part of the linker chain improved cell viability compared to the 2,6-bisbenzylidenecyclohexanone derivatives. Meanwhile, compound 11 (IC50 = 13.27 +/- A 1.78 mu M) bearing ortho hydroxyls on the aromatic rings recorded the highest radical scavenging activity as compared with quercetin (IC50 = 21.46 +/- A 0.85 mu M).
• Structure-Activity Relationships on Cinnamoyl Derivatives as Inhibitors of p300 Histone Acetyltransferase
  作者：Valentina Noemi Madia、Rosaria Benedetti、Maria Letizia Barreca、Liza Ngo、Luca Pescatori、Antonella Messore、Giovanni Pupo、Francesco Saccoliti、Sergio Valente、Antonello Mai、Luigi Scipione、Yujun George Zheng、Cristina Tintori、Maurizio Botta、Violetta Cecchetti、Lucia Altucci、Roberto Di Santo、Roberta Costi

  DOI：10.1002/cmdc.201700040

  日期：2017.8.22

  Several p300 inhibitors (i.e., histone acetyltransferase inhibitors, HATis) have been described so far, but they all suffer from low potency, lack of specificity, or low cell permeability, which thus highlights the need to find more effective inhibitors. Our cinnamoyl derivative, 2,6-bis(3-bromo-4-hydroxybenzylidene)cyclohexanone (RC56), was identified as an active and selective p300 inhibitor and was

  人p300是一种多面体转录共激活因子，在乙酰化特定赖氨酸残基上的组蛋白乙酰化中起关键作用。大量证据表明，p300与多种疾病有关，包括白血病，肿瘤和病毒感染。它参与多效性生物学作用和与疾病的联系为确定其调制如何代表合适的药物靶标提供了理论依据。迄今为止，已经描述了几种p300抑制剂（即组蛋白乙酰转移酶抑制剂HATis），但是它们都具有效力低，缺乏特异性或细胞通透性低的缺点，因此突出了寻找更有效抑制剂的需求。我们的肉桂酰基衍生物2,6-双（3-溴-4-羟基亚苄基）环己酮（RC56）被鉴定为一种活性和选择性的p300抑制剂，并被证明是研究与p300的构效关系的良好候选物。在这里，我们描述与我们的命中结构相关的新HAT的设计，合成和生物学评估。此外，我们通过诱导拟合对接和分子动力学模拟的方法研究了p300与最佳命中分子之间的相互作用，从而深入了解了影响其对目标酶活性的独特化学特征。