2,6-bis(3,4-diacetoxybenzylidene)cyclohexanone | 158610-02-7

• 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-diacetoxybenzylidene)cyclohexanone
• 英文别名: 2,6-Bis(3,4-diacetoxybenzylidene)cyclohexanone；[2-acetyloxy-4-[[3-[(3,4-diacetyloxyphenyl)methylidene]-2-oxocyclohexylidene]methyl]phenyl] acetate
• CAS: 158610-02-7
• 化学式: C₂₈H₂₆O₉
• 分子量: 506.509
• InChiKey: LBNWREGIXJIZPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  环己酮 、 3,4-二羟基苯甲醛 在 盐酸 、 4-二甲氨基吡啶 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 反应 4.0h， 生成 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

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).