(2E)-3-(5-chlorothiophen-2-yl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (2E)-3-(5-chlorothiophen-2-yl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
• 英文别名: (E)-3-(5-chlorothiophen-2-yl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
• 化学式: C₁₄H₁₁ClO₃S
• 分子量: 294.759
• InChiKey: CKTZEBLIYXBHQG-ZZXKWVIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-氯噻吩-2-甲醛 、 丹皮酚 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以1.8%的产率得到(2E)-3-(5-chlorothiophen-2-yl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Monoamine oxidase inhibitory activities of heterocyclic chalcones

  摘要：

  Studies have shown that natural and synthetic chalcones (1,3-diphenyl-2-propen-1-ones) possess monoamine oxidase (MAO) inhibition activities. Of particular importance to the present study is a report that a series of furanochalcones acts as MAO-B selective inhibitors. Since the effect of heterocyclic substitution, other than furan (and more recently thiophene, piperidine and quinoline) on the MAO inhibitory properties of the chalcone scaffold remains unexplored, the aim of this study was to synthesise and evaluate further heterocyclic chalcone analogues as inhibitors of the human MAOs. For this purpose, heterocyclic chalcone analogues that incorporate pyrrole, 5-methylthiophene, 5-chlorothiophene and 6-methoxypyridine substitution were examined. Seven of the nine synthesised compounds exhibited IC50 values <1 mu M for the inhibition of MAO-B, with all compounds exhibiting higher affinities for MAO-B compared to the MAO-A isoform. The most potent MAO-B inhibitor (4h) displays an IC50 value of 0.067 mu M while the most potent MAO-A inhibitor (4e) exhibits an IC50 value of 3.81 mu M. It was further established that selected heterocyclic chalcones are reversible and competitive MAO inhibitors. 4h, however, may exhibit tight-binding to MAO-B, a property linked to its thiophene moiety. We conclude that high potency chalcones such as 4h represent suitable leads for the development of MAO-B inhibitors for the treatment of Parkinson's disease and possibly other neurodegenerative disorders. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.09.049