(1E,4Z,6E)-7-(4-chlorophenyl)-1-{3-[(dimethylamino)methyl]-4-hydroxyphenyl}-5-hydroxyhepta-1,4,6-trien-3-one | 1529810-92-1

• 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)-7-(4-chlorophenyl)-1-{3-[(dimethylamino)methyl]-4-hydroxyphenyl}-5-hydroxyhepta-1,4,6-trien-3-one
• CAS: 1529810-92-1
• 化学式: C₂₂H₂₂ClNO₃
• 分子量: 383.875
• InChiKey: HRMKEJBPKSJYRP-STQRUKIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  60.77
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3-[(二甲氨基)甲基]-4-羟基苯甲醛 在 boron trioxide 作用下， 以 乙酸乙酯 为溶剂， 反应 5.0h， 生成 (1E,4Z,6E)-7-(4-chlorophenyl)-1-{3-[(dimethylamino)methyl]-4-hydroxyphenyl}-5-hydroxyhepta-1,4,6-trien-3-one
  参考文献：
  名称：

  Design, synthesis and anti-Alzheimer properties of dimethylaminomethyl-substituted curcumin derivatives

  摘要：

  Eight dimethylaminomethyl-substituted curcumin derivatives were designed and synthesized. The antioxidant test revealed that the synthesized compounds had higher free radical scavenging activity towards both 2,2-diphenyl-1-picrylhydrazyl free radicals (DPPH) (IC50 1.5-29.9 mu M) and galvinoxyl radicals (IC50 4.9-41.1 mu M) than the lead compound curcumin. Besides, compound 3a could effectively inhibit the Ab self-aggregation in vitro. Investigated in phosphate-buffered solutions (pH = 7.4) in the presence or absence of 0.1% FBS 3a showed a good stability while curcumin did not. Furthermore, 3a showed a good lipophilicity (logP = 3.48), suggesting a potential ability to penetrate the blood-brain-barrier. The aqueous solubility of the hydrochloride salt of 3a (16.7 mg/mL) has also been significantly improved as compared with curcumin (< 0.1 mg/mL). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.011

文献信息

• Design, synthesis and anti-Alzheimer properties of dimethylaminomethyl-substituted curcumin derivatives
  作者：Lei Fang、Shaohua Gou、Xuying Liu、Feng Cao、Lin Cheng

  DOI：10.1016/j.bmcl.2013.12.011

  日期：2014.1

  Eight dimethylaminomethyl-substituted curcumin derivatives were designed and synthesized. The antioxidant test revealed that the synthesized compounds had higher free radical scavenging activity towards both 2,2-diphenyl-1-picrylhydrazyl free radicals (DPPH) (IC50 1.5-29.9 mu M) and galvinoxyl radicals (IC50 4.9-41.1 mu M) than the lead compound curcumin. Besides, compound 3a could effectively inhibit the Ab self-aggregation in vitro. Investigated in phosphate-buffered solutions (pH = 7.4) in the presence or absence of 0.1% FBS 3a showed a good stability while curcumin did not. Furthermore, 3a showed a good lipophilicity (logP = 3.48), suggesting a potential ability to penetrate the blood-brain-barrier. The aqueous solubility of the hydrochloride salt of 3a (16.7 mg/mL) has also been significantly improved as compared with curcumin (< 0.1 mg/mL). (C) 2013 Elsevier Ltd. All rights reserved.