(2E)-1-(2'-hydroxy-3'-bromo-4',6'-dimethoxyphenyl)-3-(1-naphthyl)-2-propen-1-one | 1265608-53-4

• 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-(2'-hydroxy-3'-bromo-4',6'-dimethoxyphenyl)-3-(1-naphthyl)-2-propen-1-one
• 英文别名: (E)-1-(3-bromo-2-hydroxy-4,6-dimethoxyphenyl)-3-naphthalen-1-ylprop-2-en-1-one
• CAS: 1265608-53-4
• 化学式: C₂₁H₁₇BrO₄
• 分子量: 413.268
• InChiKey: XRWPLUNICSARQP-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 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：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-hydroxy-3-bromo-4,6-dimethoxyacetophenone 、 1-萘甲醛 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以42%的产率得到(2E)-1-(2'-hydroxy-3'-bromo-4',6'-dimethoxyphenyl)-3-(1-naphthyl)-2-propen-1-one
  参考文献：
  名称：

  Biochemical evaluation of a series of synthetic chalcone and hydrazide derivatives as novel inhibitors of cruzain from Trypanosoma cruzi

  摘要：

  Chagas' disease, a parasitic infection widely distributed throughout Latin America, is a major public health problem with devastating consequences in terms of human morbidity and mortality. The enzyme cruzain is the major cysteine protease from Trypanosoma cruzi, the etiologic agent of American trypanosomiasis or Chagas' disease, and has been selected as an attractive target for the development of novel trypanocidal drugs. In the present work, we describe the synthesis and inhibitory effects of a series of thirty-three chalcone and seven hydrazide derivatives against the enzyme cruzain from T. cruzi. Most of the compounds showed promising in vitro inhibition (IC50 values in the range of 20-60 mu M), which suggest the potential of these compounds as lead candidates for further development. Twelve compounds have not been reported before, and four of them (7, 13, 16 e 18) are among the most potent inhibitors of the series.

  DOI：

  10.1590/s0103-50532010000100021

文献信息

• Biochemical evaluation of a series of synthetic chalcone and hydrazide derivatives as novel inhibitors of cruzain from Trypanosoma cruzi
  作者：Deise M. Borchhardt、Alessandra Mascarello、Louise Domeneghini Chiaradia、Ricardo J. Nunes、Glaucius Oliva、Rosendo A. Yunes、Adriano D. Andricopulo

  DOI：10.1590/s0103-50532010000100021

  日期：——

  Chagas' disease, a parasitic infection widely distributed throughout Latin America, is a major public health problem with devastating consequences in terms of human morbidity and mortality. The enzyme cruzain is the major cysteine protease from Trypanosoma cruzi, the etiologic agent of American trypanosomiasis or Chagas' disease, and has been selected as an attractive target for the development of novel trypanocidal drugs. In the present work, we describe the synthesis and inhibitory effects of a series of thirty-three chalcone and seven hydrazide derivatives against the enzyme cruzain from T. cruzi. Most of the compounds showed promising in vitro inhibition (IC50 values in the range of 20-60 mu M), which suggest the potential of these compounds as lead candidates for further development. Twelve compounds have not been reported before, and four of them (7, 13, 16 e 18) are among the most potent inhibitors of the series.