1,4-Bis-(3,4,5-trimethoxy-phenyl)-but-2-yne-1,4-diol | 912677-66-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,4-Bis-(3,4,5-trimethoxy-phenyl)-but-2-yne-1,4-diol
• 英文别名: 1,4-Bis(3,4,5-trimethoxyphenyl)but-2-yne-1,4-diol；1,4-bis(3,4,5-trimethoxyphenyl)but-2-yne-1,4-diol
• CAS: 912677-66-8
• 化学式: C₂₂H₂₆O₈
• 分子量: 418.444
• InChiKey: PEYYSLHASRFVGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  95.8
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,4-Bis-(3,4,5-trimethoxy-phenyl)-but-2-yne-1,4-diol 在 platinum(IV) oxide 氢气 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以72%的产率得到1,4-bis(3,4,5-trimethoxyphenyl)-1,4-butanediol
  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
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 在 正丁基锂 、 乙二胺 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 4.67h， 生成 1,4-Bis-(3,4,5-trimethoxy-phenyl)-but-2-yne-1,4-diol
  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

• Direct Exploitation of the Ethynyl Moiety in Calcium Carbide Through Sealed Ball Milling
  作者：Abolfazl Hosseini、Peter R. Schreiner

  DOI：10.1002/ejoc.202000612

  日期：2020.8.2

  Sealed ball milling provides a novel way of activation of calcium carbide. No additive is required to transfer the acetylide moiety to organic molecules. Various ketones and even aryl halides can thereby be ethynylated.

  密封球磨提供了一种激活电石的新颖方法。不需要添加剂即可将乙炔部分转移至有机分子。因此，各种酮，甚至芳基卤化物都可以被乙炔基化。
• 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.