ethyl 2'-chlorocarbonyl-3,3'-dibromo-4,4'-dimethoxy-5,6,5',6'-dimethylenedioxy-biphenyl-2-carboxylate | 867169-02-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: ethyl 2'-chlorocarbonyl-3,3'-dibromo-4,4'-dimethoxy-5,6,5',6'-dimethylenedioxy-biphenyl-2-carboxylate
• 英文别名: Ethyl 6-bromo-4-(6-bromo-5-carbonochloridoyl-7-methoxy-1,3-benzodioxol-4-yl)-7-methoxy-1,3-benzodioxole-5-carboxylate
• CAS: 867169-02-6
• 化学式: C₂₀H₁₅Br₂ClO₉
• 分子量: 594.595
• InChiKey: VZIPRRSRQPEUFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-amino-3-(3-phenylmethoxypropoxyimino)propan-1-ol 、 ethyl 2'-chlorocarbonyl-3,3'-dibromo-4,4'-dimethoxy-5,6,5',6'-dimethylenedioxy-biphenyl-2-carboxylate 以89%的产率得到ethyl 6-bromo-4-[6-bromo-5-[[(3E)-1-hydroxy-3-(3-phenylmethoxypropoxyimino)propan-2-yl]carbamoyl]-7-methoxy-1,3-benzodioxol-4-yl]-7-methoxy-1,3-benzodioxole-5-carboxylate
  参考文献：
  名称：

  A solid-phase approach to DDB derivatives

  摘要：

  Since the discovery of 2,2'-dimethoxycarbonyl-4,4-dimethoxy-5,6,5',6'-biomethylenedioxy-biphenyl (DDB) as a potent anti-HBV agent, we have studied the structure-activity relationships of 4,4'-dimethoxy -5,6,5',6'-dimethenedioxy-2-alkyloxycarbonyl-2'-(4- substituted benzyl piperazin-1-yl)carbonyl-biphenyl as anti-HBV agents. Therefore, it is rational to extend this study to the 3,3'-disustituted-4,4'-dimethoxy5,6,5',6'-dimethenedioxy-2-alkyloxycarbonyl-2'-Serine derivatives. Thus, in an attempt to develop an efficient method for the preparation of a large number of DDB derivatives, the reaction between a DDB acid chloride and serine derivatives on solid support was studied. The structure of resulted compounds was confirmed by LC-MS and H-1 NMR analysis. Compounds 2a, 2d, 2f, 2j showed in vitro anti-HBV activity without significant toxicity up to 100 mu M. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.03.024
• 作为产物：
  描述：

  6-Bromo-4-(6-bromo-5-ethoxycarbonyl-7-methoxy-1,3-benzodioxol-4-yl)-7-methoxy-1,3-benzodioxole-5-carboxylic acid 在 氯化亚砜 作用下， 生成 ethyl 2'-chlorocarbonyl-3,3'-dibromo-4,4'-dimethoxy-5,6,5',6'-dimethylenedioxy-biphenyl-2-carboxylate
  参考文献：
  名称：

  A solid-phase approach to DDB derivatives

  摘要：

  Since the discovery of 2,2'-dimethoxycarbonyl-4,4-dimethoxy-5,6,5',6'-biomethylenedioxy-biphenyl (DDB) as a potent anti-HBV agent, we have studied the structure-activity relationships of 4,4'-dimethoxy -5,6,5',6'-dimethenedioxy-2-alkyloxycarbonyl-2'-(4- substituted benzyl piperazin-1-yl)carbonyl-biphenyl as anti-HBV agents. Therefore, it is rational to extend this study to the 3,3'-disustituted-4,4'-dimethoxy5,6,5',6'-dimethenedioxy-2-alkyloxycarbonyl-2'-Serine derivatives. Thus, in an attempt to develop an efficient method for the preparation of a large number of DDB derivatives, the reaction between a DDB acid chloride and serine derivatives on solid support was studied. The structure of resulted compounds was confirmed by LC-MS and H-1 NMR analysis. Compounds 2a, 2d, 2f, 2j showed in vitro anti-HBV activity without significant toxicity up to 100 mu M. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.03.024

文献信息

• A solid-phase approach to DDB derivatives
  作者：Xiuxiang Qi、Xiaolai Wang、Limin Wang、Qiang Wang、Senxiang Cheng、Jishuan Suo、Junbiao Chang

  DOI：10.1016/j.ejmech.2005.03.024

  日期：2005.8

  Since the discovery of 2,2'-dimethoxycarbonyl-4,4-dimethoxy-5,6,5',6'-biomethylenedioxy-biphenyl (DDB) as a potent anti-HBV agent, we have studied the structure-activity relationships of 4,4'-dimethoxy -5,6,5',6'-dimethenedioxy-2-alkyloxycarbonyl-2'-(4- substituted benzyl piperazin-1-yl)carbonyl-biphenyl as anti-HBV agents. Therefore, it is rational to extend this study to the 3,3'-disustituted-4,4'-dimethoxy5,6,5',6'-dimethenedioxy-2-alkyloxycarbonyl-2'-Serine derivatives. Thus, in an attempt to develop an efficient method for the preparation of a large number of DDB derivatives, the reaction between a DDB acid chloride and serine derivatives on solid support was studied. The structure of resulted compounds was confirmed by LC-MS and H-1 NMR analysis. Compounds 2a, 2d, 2f, 2j showed in vitro anti-HBV activity without significant toxicity up to 100 mu M. (c) 2005 Elsevier SAS. All rights reserved.