N-(3-((E)-3-(3-bromo-2,4,6-trimethoxyphenyl)acryloyl)phenyl)-4-methoxybenzamide | 1349690-85-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: N-(3-((E)-3-(3-bromo-2,4,6-trimethoxyphenyl)acryloyl)phenyl)-4-methoxybenzamide
• 英文别名: N-(3-((e)-3-(3-bromo-2,4,6-trimethoxyphenyl)acryloyl)phenyl)-4-methoxybenzamide；N-[3-[(E)-3-(3-bromo-2,4,6-trimethoxyphenyl)prop-2-enoyl]phenyl]-4-methoxybenzamide
• CAS: 1349690-85-2
• 化学式: C₂₆H₂₄BrNO₆
• 分子量: 526.384
• InChiKey: IZPCLEUANGPMAP-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,4,6-三甲氧基苯甲醛 在 溴 、 溶剂黄146 、 sodium hydroxide 作用下， 反应 24.0h， 生成 N-(3-((E)-3-(3-bromo-2,4,6-trimethoxyphenyl)acryloyl)phenyl)-4-methoxybenzamide
  参考文献：
  名称：

  Synthesis and biological evaluation of novel curcumin analogues as anti-inflammatory, anti-cancer and anti-oxidant agents

  摘要：

  A series of novel curcumin analogues 5a-m were synthesized by Claisen-Schmidt condensation of various aromatic and heteroaromatic amides of 3-aminoactophenones 4a-m with 3-bromo-2,4,6-trimethoxybenzaldehyde and characterized by IR, H-1 NMR and mass spectroscopic analysis and were evaluated for anti-inflammatory, anti-cancer and anti-oxidant activity. Out of the 13 synthesized compounds, compounds 5f, 5j and 5m were excellent inhibitors of TNF-alpha and IL-6. Compounds 5c, 5e, 5b and 5d showed potent COX-2 inhibition, compounds 5d and 5f have shown good trypsin inhibition and compounds 5e, 5g and 5c exhibited excellent beta-glucuronidase inhibition. Compounds 5l and 5m showed potent anti-cancer activity against selected five human cancer cell lines. All the compounds exhibited moderate free radical scavenging activity, while compounds 5a and 5m were excellent OH radical scavengers.

  DOI：

  10.1007/s00044-011-9834-7

文献信息

• Synthesis and biological evaluation of novel curcumin analogues as anti-inflammatory, anti-cancer and anti-oxidant agents
  作者：Babasaheb P. Bandgar、Baliram S. Hote、Shivkumar S. Jalde、Rajesh N. Gacche

  DOI：10.1007/s00044-011-9834-7

  日期：2012.10

  A series of novel curcumin analogues 5a-m were synthesized by Claisen-Schmidt condensation of various aromatic and heteroaromatic amides of 3-aminoactophenones 4a-m with 3-bromo-2,4,6-trimethoxybenzaldehyde and characterized by IR, H-1 NMR and mass spectroscopic analysis and were evaluated for anti-inflammatory, anti-cancer and anti-oxidant activity. Out of the 13 synthesized compounds, compounds 5f, 5j and 5m were excellent inhibitors of TNF-alpha and IL-6. Compounds 5c, 5e, 5b and 5d showed potent COX-2 inhibition, compounds 5d and 5f have shown good trypsin inhibition and compounds 5e, 5g and 5c exhibited excellent beta-glucuronidase inhibition. Compounds 5l and 5m showed potent anti-cancer activity against selected five human cancer cell lines. All the compounds exhibited moderate free radical scavenging activity, while compounds 5a and 5m were excellent OH radical scavengers.