3-(4-bromobutoxy)benzamide | 1384187-38-5

• 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-(4-bromobutoxy)benzamide
• 英文别名: 3-(4-Bromobutoxy)benzamide
• CAS: 1384187-38-5
• 化学式: C₁₁H₁₄BrNO₂
• 分子量: 272.142
• InChiKey: FQKZKVDOAFXDRY-UHFFFAOYSA-N

物化性质

• 沸点：
  399.7±27.0 °C(Predicted)
• 密度：
  1.396±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  1H-1,2,4-三唑 、 3-(4-bromobutoxy)benzamide 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以76.8%的产率得到3-(4-(1H-1,2,4-triazol-1-yl)butoxy)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
• 作为产物：
  描述：

  间羟基苯甲酸 在 氯化亚砜 、 氨 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 甲苯 、 乙腈 为溶剂， 反应 40.5h， 生成 3-(4-bromobutoxy)benzamide
  参考文献：
  名称：

  新型3-O-芳基烷基苯甲酰胺衍生物作为FtsZ抑制剂的合成及抑菌活性

  摘要：

  设计，合成和评估了一系列新颖的3-O-芳基烷基苯甲酰胺衍生物作为FtsZ抑制剂，它们对枯草芽孢杆菌和金黄色葡萄球菌具有细胞分裂抑制活性，并且对革兰氏阳性细菌的各种表型具有体外抗菌活性。与3-MBA相比，该系列药物的靶向活性和体外抗菌活性显着提高。其中，3-O-烷基苯甲酰胺4-8和3-O-溴烷基苯甲酰胺9和10对金黄色葡萄球菌ATCC25923，金黄色葡萄球菌ATCC29213（MRSA）和金黄色葡萄球菌PR的三种表型显示出显着改善的活性。初步的结构活性关系表明，3-O-烷基侧链的延长导致抗菌活性大大提高，

  DOI：

  10.2174/1570180811310040005

文献信息

• Synthesis and Biological Evaluation of Novel FtsZ‐targeted 3‐arylalkoxy‐2,6‐difluorobenzamides as Potential Antimicrobial Agents
  作者：Shengsheng Qiang、Changde Wang、Henrietta Venter、Xin Li、Yi Wang、Liwei Guo、Ruixin Ma、Shutao Ma

  DOI：10.1111/cbdd.12658

  日期：2016.2

  Novel series of 3‐O‐arylalkylbenzamide and 3‐O‐arylalkyl‐2,6‐difluorobenzamide derivatives were synthesized and evaluated for their on‐target activity and antibacterial activity. The results indicated that the 3‐O‐arylalkyl‐2,6‐difluorobenzamide derivatives possessed much better on‐target activity and antibacterial activity than the 3‐O‐arylalkylbenzamide derivatives. Among them, 3‐O‐chlorobenzyl derivative 36 was the most effective in antibacterial activity (0.5, 4, and 8 μg/mL) against Bacillus subtilis ATCC9372, methicillin‐resistant Staphylococcus aureus ATCC29213, and penicillin‐resistant Staphylococcus aureus PR, while 3‐O‐methylbenzyl derivative 41 only exhibited the most potent activity (2 μg/mL) against Staphylococcus aureus ATCC25923.
• 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.
• The Synthesis and Antibacterial Activity of Novel 3-O-arylalkylbenzamide Derivatives as FtsZ Inhibitors
  作者：Siti Ma、Rongmei Wang、Yuanze Wang、Jichao Cao、Shutao Ma

  DOI：10.2174/1570180811310040005

  日期：2013.3.1

  A series of novel 3-O-arylalkylbenzamide derivatives as FtsZ inhibitors was designed, synthesized and evaluated for their cell division inhibitory activity against B. subtilis and S. aureus, and in vitro antibacterial activity against various phenotypes of Gram-positive bacteria. This series showed significantly improved on-target activity and in vitro antibacterial activity compared with 3-MBA. Among

  设计，合成和评估了一系列新颖的3-O-芳基烷基苯甲酰胺衍生物作为FtsZ抑制剂，它们对枯草芽孢杆菌和金黄色葡萄球菌具有细胞分裂抑制活性，并且对革兰氏阳性细菌的各种表型具有体外抗菌活性。与3-MBA相比，该系列药物的靶向活性和体外抗菌活性显着提高。其中，3-O-烷基苯甲酰胺4-8和3-O-溴烷基苯甲酰胺9和10对金黄色葡萄球菌ATCC25923，金黄色葡萄球菌ATCC29213（MRSA）和金黄色葡萄球菌PR的三种表型显示出显着改善的活性。初步的结构活性关系表明，3-O-烷基侧链的延长导致抗菌活性大大提高，