(2E)-1-(3',4'-dimethoxyphenyl)-3-(2-naphthyl)-2-propen-1-one

• 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: (2E)-1-(3',4'-dimethoxyphenyl)-3-(2-naphthyl)-2-propen-1-one
• 英文别名: 1-(3,4-Dimethoxyphenyl)-3-(naphthalen-2-yl)prop-2-en-1-one；(E)-1-(3,4-dimethoxyphenyl)-3-naphthalen-2-ylprop-2-en-1-one
• 化学式: C₂₁H₁₈O₃
• 分子量: 318.372
• InChiKey: VOCWKGFFNOMSGD-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-萘甲醛 、 3,4-二甲氧基苯乙酮 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 以96%的产率得到(2E)-1-(3',4'-dimethoxyphenyl)-3-(2-naphthyl)-2-propen-1-one
  参考文献：
  名称：

  Synthetic chalcones as efficient inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase PtpA

  摘要：

  In the search for lead compounds for new drugs for tuberculosis, the activity of 38 synthetic chalcones were assayed for their potential inhibitory action towards a protein tyrosine phosphatase from Mycobacterium tuberculosis - PtpA. The compounds were obtained by aldolic condensation between aldehydes and acetophenones, under basic conditions. Five compounds presented moderate or good activity. The structure - activity analysis reveals that the predominant factor for the activity is the molecule planarity/hydrophobicity and the nature of the substituents. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.105

文献信息

• In vitro and in vivo efficacy and in vitro metabolism of 1-phenyl-3-aryl-2-propen-1-ones against Plasmodium falciparum
  作者：Clare E. Gutteridge、Daniel A. Nichols、Sean M. Curtis、Darshan S. Thota、Joseph V. Vo、Lucia Gerena、Gettayacamin Montip、Constance O. Asher、Damaris S. Diaz、Charles A. DiTusa、Kirsten S. Smith、Apurba K. Bhattacharjee

  DOI：10.1016/j.bmcl.2006.08.009

  日期：2006.11

  Investigation of a series of 1-phenyl-3-aryl-2-propen-1-ones resulted in the identification of nine inhibitors with submicromolar efficacy against at least one Plasmodium falciparum strain in vitro. These inhibitors were inactive when given orally in a Plasmodium berghei infected mouse model. Significant compound degradation occurred upon their exposure to a liver microsome preparation, suggesting metabolic instability may be responsible for the lack of activity in vivo. (c) 2006 Elsevier Ltd. All rights reserved.