1-(4-hydroxyphenyl)-4-(3,4-dimethoxyphenyl)butane-1,4-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-hydroxyphenyl)-4-(3,4-dimethoxyphenyl)butane-1,4-dione
• 英文别名: 1-(3,4-dimethoxyphenyl)-4-(4-hydroxyphenyl)butane-1,4-dione；1-(3,4-Dimethoxyphenyl)-4-(4-hydroxyphenyl)butane-1,4-dione
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: QAVZSNYHMGJYAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  1-(3,4-dimethoxyphenyl)prop-2-en-1-one 、 对羟基苯甲醛 在 3-乙基-5-(2-羟乙基)-4-甲基噻唑溴化物 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 以38%的产率得到1-(4-hydroxyphenyl)-4-(3,4-dimethoxyphenyl)butane-1,4-dione
  参考文献：
  名称：

  Synthesis and trypanocidal activity of 1,4-bis-(3,4,5-trimethoxy-phenyl)-1,4-butanediol and 1,4-bis-(3,4-dimethoxyphenyl)-1,4-butanediol

  摘要：

  Chagas' disease is endemic in Central and South American countries. Specific chemotherapy with nifurtimox or benznidazole has been recommended for treatment of recent infection but they have limited efficacy. The natural products veraguensin (1) and grandisin (2) have shown potent in vitro activity against trypomastigote parasite (Y strain) with IC50 2.3 mu M (1) and 3.7 mu M (2). We report herein the synthesis and in vitro trypanocidal evaluation of symmetrical and unsymmetrical 1,4-diaryl-1,4-diol derivatives as potential trypanocidal analogs of natural compounds 1 and 2. Among the synthesized products, compounds 1,4-bis-(3,4,5-trimethoxyphenyl)-1,4-butanediol (6a) and 1,4-bis-(3,4-dimethoxyphenyl)-1,4-butanediol (6b) showed better activity against Trypanosoma cruzi trypomastigotes with IC50 100 and 105 mu M (Y strain), respectively, and 110 mu M (Bolivia strain) for both compounds. However, the most active compound of this series was 1,4-bis-(3,4-dimethoxyphenyl)butane-1,4-dione (7b) with IC50 10 and 200 mu M against Y and Bolivia strains, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.006

文献信息

• Synthesis and trypanocidal activity of 1,4-bis-(3,4,5-trimethoxy-phenyl)-1,4-butanediol and 1,4-bis-(3,4-dimethoxyphenyl)-1,4-butanediol
  作者：Lilian Sibelle Campos Bernardes、Massuo Jorge Kato、Sérgio Albuquerque、Ivone Carvalho

  DOI：10.1016/j.bmc.2006.07.006

  日期：2006.11

  Chagas' disease is endemic in Central and South American countries. Specific chemotherapy with nifurtimox or benznidazole has been recommended for treatment of recent infection but they have limited efficacy. The natural products veraguensin (1) and grandisin (2) have shown potent in vitro activity against trypomastigote parasite (Y strain) with IC50 2.3 mu M (1) and 3.7 mu M (2). We report herein the synthesis and in vitro trypanocidal evaluation of symmetrical and unsymmetrical 1,4-diaryl-1,4-diol derivatives as potential trypanocidal analogs of natural compounds 1 and 2. Among the synthesized products, compounds 1,4-bis-(3,4,5-trimethoxyphenyl)-1,4-butanediol (6a) and 1,4-bis-(3,4-dimethoxyphenyl)-1,4-butanediol (6b) showed better activity against Trypanosoma cruzi trypomastigotes with IC50 100 and 105 mu M (Y strain), respectively, and 110 mu M (Bolivia strain) for both compounds. However, the most active compound of this series was 1,4-bis-(3,4-dimethoxyphenyl)butane-1,4-dione (7b) with IC50 10 and 200 mu M against Y and Bolivia strains, respectively. (c) 2006 Elsevier Ltd. All rights reserved.