3-(2-bromoethoxy)benzamide | 125174-24-5

• 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: 3-(2-bromoethoxy)benzamide
• CAS: 125174-24-5
• 化学式: C₉H₁₀BrNO₂
• 分子量: 244.088
• InChiKey: NIPWUFWIGIXQFH-UHFFFAOYSA-N

物化性质

• 沸点：
  363.1±27.0 °C(Predicted)
• 密度：
  1.508±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-bromoethoxy)benzamide 在 18-冠醚-6 、 potassium phtalimide 、 甲胺 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 6.0h， 生成 3-(2-氨基乙氧基)苯甲酰胺
  参考文献：
  名称：

  发现新型pERK1 / 2或β-arrestin偏爱的5-HT1A受体偏向激动剂：多种治疗样与副作用的关系。

  摘要：

  获得了对5-羟色胺5-HT 1A受体具有高亲和力和选择性的新型1-（1-苯甲酰基哌啶丁-4-基）甲胺衍生物，并在四种功能测定中进行了测试：ERK1 / 2磷酸化，腺苷酸环化酶抑制，钙动员和β-抑制蛋白的募集。选择化合物44和56（分别为2-甲基氨基苯氧基乙基和2-（1 H-吲哚-4-基氧基）乙基衍生物）作为具有高度差异性的“信号指纹”的偏向激动剂，这些信号被翻译成不同的体内特征。在体外，44显示出对ERK1 / 2磷酸化的偏向激动作用，而在体内，它在大鼠Porsolt强迫游泳试验中优先发挥了抗抑郁样作用。相反，化合物56表现出一流的特性：它在体外优先有效地激活β-arrestin募集，并在体内有效引起下唇缩回，这是“ 5-羟色胺能综合症”的一个组成部分。两种化合物均显示出良好的可显影性。提出的5-HT 1A受体偏向激动剂，优先针对各种信号传导途径，有可能成为独特的中枢神经系统病理学的候选药

  DOI：

  10.1021/acs.jmedchem.0c00814
• 作为产物：
  描述：

  间羟基苯甲酸 在 ammonium hydroxide 、 氯化亚砜 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 4.5h， 生成 3-(2-bromoethoxy)benzamide
  参考文献：
  名称：

  Synthesis and on-target antibacterial activity of novel 3-elongated arylalkoxybenzamide derivatives as inhibitors of the bacterial cell division protein FtsZ

  摘要：

  Novel 3-elongated arylalkoxybenzamide derivatives were designed, synthesized and evaluated for their cell division inhibitory activity and antibacterial activity. Among them, the subseries of 3-alkyloxybenzamide derivatives exhibited greatly improved on-target activity against Bacillus subtilis and Staphylococcus aureus, and remarkably increased antibacterial activity against B. subtilis ATCC9372, penicillin-susceptible S. aureus ATCC25923, methicillin-resistant S. aureus ATCC29213 (MRSA) and penicillin-resistant S. aureus PR compared with 3-methoxybenzamide. In contrast, the subseries of 3-phenoxyaklyloxybenzamide, 3-heteroarylalkyloxybenzamide and 3-heteroarylthioalkyloxybenzamide derivatives only showed a significant improvement in on-target activity and antibacterial activity against B. subtilis ATCC9372. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.056

文献信息

• Selective class III antiarrhythmic agents. 1. Bis(arylalkyl)amines
  作者：Peter E. Cross、John E. Arrowsmith、Geoffrey N. Thomas、Michael Gwilt、Roger A. Burges、Alan J. Higgins

  DOI：10.1021/jm00166a011

  日期：1990.4

  A series of bis(arylalkyl)amines is described and their effects on prolonging effective refractory period in isolated cardiac tissue listed. Most compounds prolonged the cardiac action potential without significantly altering the maximum rate of depolarization and may be defined as selective class III antiarrhythmic agents. It was found that a particularly advantageous structural feature was to have a methanesulfonamido moiety on both of the aryl rings. Thus, compound 16 [1-(4-methanesulfonamidophenoxy)2-[N-(4-methanesulfonamidophene thyl)-N- methylamine]ethane] was selected for further investigations. The compound is highly potent and selective class III agent which acts by blockade of cardiac potassium channels.
• CROSS, PETER E.;ARROWSMITH, JOHN E.;THOMAS, GEOFFREY N.;GWILT, MICHAEL;BU+, J. MED. CHEM., 33,(1990) N, C. 1151-1155
  作者：CROSS, PETER E.、ARROWSMITH, JOHN E.、THOMAS, GEOFFREY N.、GWILT, MICHAEL、BU+

  DOI：——

  日期：——
• Discovery of Novel pERK1/2- or β-Arrestin-Preferring 5-HT_1A Receptor-Biased Agonists: Diversified Therapeutic-like versus Side Effect Profile
  作者：Joanna Sniecikowska、Monika Gluch-Lutwin、Adam Bucki、Anna Więckowska、Agata Siwek、Magdalena Jastrzebska-Wiesek、Anna Partyka、Daria Wilczyńska、Karolina Pytka、Gniewomir Latacz、Katarzyna Przejczowska-Pomierny、Elżbieta Wyska、Anna Wesołowska、Maciej Pawłowski、Adrian Newman-Tancredi、Marcin Kolaczkowski

  DOI：10.1021/acs.jmedchem.0c00814

  日期：2020.10.8

  in vivo, a component of “serotonergic syndrome”. Both compounds showed promising developability properties. The presented 5-HT1A receptor-biased agonists, preferentially targeting various signaling pathways, have the potential to become drug candidates for distinct central nervous system pathologies and possessing accentuated therapeutic activity and reduced side effects.

  获得了对5-羟色胺5-HT 1A受体具有高亲和力和选择性的新型1-（1-苯甲酰基哌啶丁-4-基）甲胺衍生物，并在四种功能测定中进行了测试：ERK1 / 2磷酸化，腺苷酸环化酶抑制，钙动员和β-抑制蛋白的募集。选择化合物44和56（分别为2-甲基氨基苯氧基乙基和2-（1 H-吲哚-4-基氧基）乙基衍生物）作为具有高度差异性的“信号指纹”的偏向激动剂，这些信号被翻译成不同的体内特征。在体外，44显示出对ERK1 / 2磷酸化的偏向激动作用，而在体内，它在大鼠Porsolt强迫游泳试验中优先发挥了抗抑郁样作用。相反，化合物56表现出一流的特性：它在体外优先有效地激活β-arrestin募集，并在体内有效引起下唇缩回，这是“ 5-羟色胺能综合症”的一个组成部分。两种化合物均显示出良好的可显影性。提出的5-HT 1A受体偏向激动剂，优先针对各种信号传导途径，有可能成为独特的中枢神经系统病理学的候选药
• Synthesis and on-target antibacterial activity of novel 3-elongated arylalkoxybenzamide derivatives as inhibitors of the bacterial cell division protein FtsZ
  作者：Siti Ma、Chao Cong、Xiaohui Meng、Shasha Cao、Hongkun Yang、Yuanyuan Guo、Xueyi Lu、Shutao Ma

  DOI：10.1016/j.bmcl.2013.05.056

  日期：2013.7

  Novel 3-elongated arylalkoxybenzamide derivatives were designed, synthesized and evaluated for their cell division inhibitory activity and antibacterial activity. Among them, the subseries of 3-alkyloxybenzamide derivatives exhibited greatly improved on-target activity against Bacillus subtilis and Staphylococcus aureus, and remarkably increased antibacterial activity against B. subtilis ATCC9372, penicillin-susceptible S. aureus ATCC25923, methicillin-resistant S. aureus ATCC29213 (MRSA) and penicillin-resistant S. aureus PR compared with 3-methoxybenzamide. In contrast, the subseries of 3-phenoxyaklyloxybenzamide, 3-heteroarylalkyloxybenzamide and 3-heteroarylthioalkyloxybenzamide derivatives only showed a significant improvement in on-target activity and antibacterial activity against B. subtilis ATCC9372. (C) 2013 Elsevier Ltd. All rights reserved.