(E)-3-(4-acetylaminophenyl)-1-(2,5-dimethoxyphenyl)-2-propen-1-one | 127033-93-6

• 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: (E)-3-(4-acetylaminophenyl)-1-(2,5-dimethoxyphenyl)-2-propen-1-one
• 英文别名: 4-acetamido-2',5'-dimethoxychalcone；N-[4-[(E)-3-(2,5-dimethoxyphenyl)-3-oxoprop-1-enyl]phenyl]acetamide
• CAS: 127033-93-6
• 化学式: C₁₉H₁₉NO₄
• 分子量: 325.364
• InChiKey: PCYNLFLEALAQPY-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(4-acetylaminophenyl)-1-(2,5-dimethoxyphenyl)-2-propen-1-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以38%的产率得到(E)-3-(4-acetylaminophenyl)-1-(2',5'-dihydroxyphenyl)-2-propen-1-one
  参考文献：
  名称：

  Chalcones as positive allosteric modulators of α7 nicotinic acetylcholine receptors: A new target for a privileged structure

  摘要：

  The alpha 7 acetylcholine nicotine receptor is a ligand-gated ion channel that is involved in cognition disorders, schizophrenia, pain and inflammation among other diseases. Therefore, the development of new agents that target this receptor has great significance. Positive allosteric modulators might be advantageous, since they facilitate receptor responses without directly interacting with the agonist binding site. Here we report the search for and further design of new positive allosteric modulators having the relatively simple chalcone structure. From the natural product isoliquiritigenin as starting point, chalcones substituted with hydroxyl groups at defined locations were identified as optimal and specific promoters of alpha 7 nicotinic function. The most potent compound (2,4,2',5'-tetrahydroxychalcone, 111) was further characterized showing its potential as neuroprotective, analgesic and cognitive enhancer, opening the way for future developments around the chalcone structure. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.039
• 作为产物：
  描述：

  2,5-二甲氧基苯乙酮 、 对乙酰氨基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 (E)-3-(4-acetylaminophenyl)-1-(2,5-dimethoxyphenyl)-2-propen-1-one
  参考文献：
  名称：

  Chalcones: a new class of antimitotic agents

  摘要：

  A series of chalcones was evaluated as antimitotic agents. One of these, (E)-1-(2,5-dimethoxyphenyl)-3-[4-(dimethylamino)phenyl]-2-methyl-2-pr open- 1-one) (73), was found to be an effective antimitotic agent at a concentration of 4 nM in an in vitro HeLa cell test system. When evaluated in experimental tumor models in vivo, this compound exhibited antitumor activity against L1210 leukemia and B16 melanoma.

  DOI：

  10.1021/jm00169a021

文献信息

• STEMERICK, D. M.;SUNKARA, SAI P.;EDWARDS, M. L.
  作者：STEMERICK, D. M.、SUNKARA, SAI P.、EDWARDS, M. L.

  DOI：——

  日期：——
• ANDERSON, DAVID B.;SCHMIEGEL, KLAUS K.;VEENHUIZEN, EDWARD L.;TUTTLE, RONA+
  作者：ANDERSON, DAVID B.、SCHMIEGEL, KLAUS K.、VEENHUIZEN, EDWARD L.、TUTTLE, RONA+

  DOI：——

  日期：——
• Method of treating multiple sclerosis with chalcone derivatives
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0286083B1

  公开（公告）日：1993-08-04
• Controlling the growth of tumor tissue with chalcone derivatives
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0288794B1

  公开（公告）日：1994-06-08
• Methods for treating gout with chalcone derivatives
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0287901B1

  公开（公告）日：1990-08-01