N-(4-bromo-2,3-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide | 1254068-16-0

• 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: N-(4-bromo-2,3-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide
• 英文别名: N-[2-(4-bromo-2,3-dimethoxyphenyl)ethyl]-2-(3,4-dimethoxyphenyl)acetamide
• CAS: 1254068-16-0
• 化学式: C₂₀H₂₄BrNO₅
• 分子量: 438.318
• InChiKey: CPVQWSIMXBHZSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(4-bromo-2,3-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide 在 bis-triphenylphosphine-palladium(II) chloride 、 1,2,3,4-四氢萘 、 10% Pd/C 、 caesium carbonate 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 1.17h， 生成 1-[(3,4-Dimethoxyphenyl)methyl]-5,6-dimethoxy-7-phenylisoquinoline
  参考文献：
  名称：

  Antibacterial activity of substituted dibenzo[a,g]quinolizin-7-ium derivatives

  摘要：

  Berberine is a substituted dibenzo[a,g]quinolizin-7-ium derivative whose modest antibiotic activity is derived from its disruptive impact on the function of the essential bacterial cell division protein FtsZ. The present study reveals that the presence of a biphenyl substituent at either the 2- or 12-position of structurally-related dibenzo[a,g]quinolizin-7-ium derivatives significantly enhances antibacterial potency versus Staphylococcus aureus and Enterococcus faecalis. Studies with purified S. aureus FtsZ demonstrate that both 2- and 12-biphenyl dibenzo[a,g]quinolizin-7-ium derivatives act as enhancers of FtsZ self-polymerization. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.123
• 作为产物：
  描述：

  1-bromo-2,3-dimethoxy-4-(2-nitrovinyl)benzene 在 sodium tetrahydroborate 、 sodium carbonate 、 溶剂黄146 、 锌 作用下， 以 1,4-二氧六环 、 乙醇 、 氯仿 为溶剂， 反应 1.58h， 生成 N-(4-bromo-2,3-dimethoxyphenethyl)-2-(3,4-dimethoxyphenyl)acetamide
  参考文献：
  名称：

  Antibacterial activity of substituted dibenzo[a,g]quinolizin-7-ium derivatives

  摘要：

  Berberine is a substituted dibenzo[a,g]quinolizin-7-ium derivative whose modest antibiotic activity is derived from its disruptive impact on the function of the essential bacterial cell division protein FtsZ. The present study reveals that the presence of a biphenyl substituent at either the 2- or 12-position of structurally-related dibenzo[a,g]quinolizin-7-ium derivatives significantly enhances antibacterial potency versus Staphylococcus aureus and Enterococcus faecalis. Studies with purified S. aureus FtsZ demonstrate that both 2- and 12-biphenyl dibenzo[a,g]quinolizin-7-ium derivatives act as enhancers of FtsZ self-polymerization. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.123

文献信息

• [EN] ANTIMICROBIAL AGENTS<br/>[FR] AGENTS ANTIMICROBIENS
  申请人：UNIV RUTGERS

  公开号：WO2010127307A1

  公开（公告）日：2010-11-04

  The invention provides a compound of formula (I): or a salt or prodrug thereof, wherein Y, W, Z, Z1, Z2, Z3, Z4, and R1- R12 have any of the values described in the specification, as well as compositions comprising a compound of formula (I). The compounds are useful as antibacterial agents.

  这项发明提供了一个式(I)的化合物：或其盐或前药，其中Y、W、Z、Z1、Z2、Z3、Z4和R1-R12具有规范中描述的任何值，以及包含式(I)的化合物的组合物。这些化合物可用作抗菌剂。
• ANTIMICROBIAL AGENTS
  申请人：LaVoie Edmond J.

  公开号：US20120059026A1

  公开（公告）日：2012-03-08

  The invention provides a compound of formula (I): or a salt or prodrug thereof, wherein Y, W, Z, Z 1 , Z 2 , Z 3 , Z 4 , and R 1 -R 12 have any of the values described in the specification, as well as compositions comprising a compound of formula (I). The compounds are useful as antibacterial agents.

  本发明提供一种式子(I)的化合物：或其盐或前药，其中Y、W、Z、Z1、Z2、Z3、Z4和R1-R12具有说明书中描述的任何值，以及包含式(I)的化合物的组合物。这些化合物可用作抗菌剂。
• US8933096B2
  申请人：——

  公开号：US8933096B2

  公开（公告）日：2015-01-13
• US9227966B2
  申请人：——

  公开号：US9227966B2

  公开（公告）日：2016-01-05
• Antibacterial activity of substituted dibenzo[a,g]quinolizin-7-ium derivatives
  作者：Ajit Parhi、Songfeng Lu、Cody Kelley、Malvika Kaul、Daniel S. Pilch、Edmond J. LaVoie

  DOI：10.1016/j.bmcl.2012.08.123

  日期：2012.11

  Berberine is a substituted dibenzo[a,g]quinolizin-7-ium derivative whose modest antibiotic activity is derived from its disruptive impact on the function of the essential bacterial cell division protein FtsZ. The present study reveals that the presence of a biphenyl substituent at either the 2- or 12-position of structurally-related dibenzo[a,g]quinolizin-7-ium derivatives significantly enhances antibacterial potency versus Staphylococcus aureus and Enterococcus faecalis. Studies with purified S. aureus FtsZ demonstrate that both 2- and 12-biphenyl dibenzo[a,g]quinolizin-7-ium derivatives act as enhancers of FtsZ self-polymerization. (C) 2012 Elsevier Ltd. All rights reserved.