1,4-bis-(3,4-dimethoxy-phenyl)-butane-1,4-diol | 102454-96-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,4-bis-(3,4-dimethoxy-phenyl)-butane-1,4-diol
• 英文别名: 1,4-Bis-(3,4-dimethoxy-phenyl)-butan-1,4-diol；1,4-Bis(3,4-dimethoxyphenyl)butane-1,4-diol
• CAS: 102454-96-6
• 化学式: C₂₀H₂₆O₆
• 分子量: 362.423
• InChiKey: NRVJYKDHOZVOTJ-UHFFFAOYSA-N

物化性质

• 沸点：
  544.0±50.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,4-bis-(3,4-dimethoxy-phenyl)-butane-1,4-diol 在 溶剂黄146 作用下， 生成 1-(3',4'-dimethoxyphenyl)-6,7-dimethoxynaphthalene
  参考文献：
  名称：

  Traverso, Gazzetta Chimica Italiana, 1959, vol. 89, p. 1818,1823

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(3,4-dimethoxyphenyl)prop-2-en-1-one 在 sodium tetrahydroborate 、 3-乙基-5-(2-羟乙基)-4-甲基噻唑溴化物 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 水 为溶剂， 反应 36.0h， 生成 1,4-bis-(3,4-dimethoxy-phenyl)-butane-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

• Conformation and activity of tetrahydrofuran lignans and analogs as specific platelet-activating-factor antagonists
  作者：Tesfaye Biftu、Nancy F. Gamble、Thomas Doebber、San Bao Hwang、Tsung Ying Shen、James Snyder、James P. Springer、Robert Stevenson

  DOI：10.1021/jm00160a020

  日期：1986.10

  4-dimethoxyphenyl)tetrahydrofuran and four corresponding desmethyl analogues were prepared and assayed as inhibitors of platelet activating factor (PAF) receptor binding to rabbit platelet plasma membranes. The inhibition by these isomers is stereodependent and varies with the gross shape of the molecules as determined by the molecular mechanics program MM2. The most potent PAF antagonist in this group

  制备了3,4-二甲基-2,5-双（3,4-二甲氧基苯基）四氢呋喃的六个（外消旋或内消旋）异构体和四个相应的去甲基类似物，并将其检测为血小板活化因子（PAF）受体与兔结合的抑制剂血小板质膜。这些异构体的抑制作用是立体依赖性的，并随分子力学程序MM2确定的分子总体形状而变化。这组化合物中最有效的PAF拮抗剂是反式-2,5-双（3,4,5-三甲氧基苯基）四氢呋喃（L-652,731，14），IC50为0.02 microM。
• A novel Friedel-Crafts reaction: synthesis of 4-phenylnaphthalen-1-ols
  作者：Jai Tung Huang、Tsann Long Su、Kyoichi A. Watanabe

  DOI：10.1021/jo00015a049

  日期：1991.7
• BIFTU, T.;HWANG, SAN-BAO;DOEBBER, T. W.;BEATTIE, T. R.;SHEN, TSUNG-YING
  作者：BIFTU, T.、HWANG, SAN-BAO、DOEBBER, T. W.、BEATTIE, T. R.、SHEN, TSUNG-YING

  DOI：——

  日期：——
• PHARMACOLOGICALLY ACTIVE COMPOUNDS AND MIXTURES THEREOF, ORGANIC COMPOSITIONS AND METAL SALTS
  申请人：CHEMEX PHARMACEUTICALS, INC.

  公开号：EP0290442A1

  公开（公告）日：1988-11-17
• EP0290442A4
  申请人：——

  公开号：EP0290442A4

  公开（公告）日：1990-07-03