4-[2-(2-Bromophenyl)-2-oxoethoxy]benzaldehyde | 1393890-86-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[2-(2-Bromophenyl)-2-oxoethoxy]benzaldehyde
• CAS: 1393890-86-2
• 化学式: C₁₅H₁₁BrO₃
• mdl: MFCD15480378
• 分子量: 319.155
• InChiKey: KWYCTFJUADFSSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-(4-oxo-2-thioxothiazolidin-3-yl)-3-phenylpropanoic acid 、 4-[2-(2-Bromophenyl)-2-oxoethoxy]benzaldehyde 在 哌啶 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以71%的产率得到(S,Z)-2-(5-(4-(2-(2-bromophenyl)-2-oxoethoxy)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)-3-phenylpropanoic acid
  参考文献：
  名称：

  Synthesis and bioactivity evaluation of rhodanine derivatives as potential anti-bacterial agents

  摘要：

  Five series of (Z)-5-(4-(2-oxo-2-phenylethoxy)benzylidene)-2-thioxothiazolidin-4-one derivatives (I-V) were synthesized, characterized, and evaluated for their anti-bacterial activity. Most of the synthesized compounds showed potent inhibition against several Gram-positive bacteria (including multidrug-resistant clinical isolates) with MIC values in the range of 1-32 mu g/mL. Compounds IIIi, Vb and Vc presented the most potent activity, showing four-fold more potency than norfloxacin (MIC = 8 mu g/mL and 4 mu g/mL) and 64-fold more activity than oxacillin (MIC > 64 mu g/mL) against MRSA CCARM 3167 and 3506 strains with MIC values of 1 mu g/mL, and 64-fold more potency than norfloxacin (MIC > 64 mu g/mL) and comparable activity to oxacillin (MIC = 1 mu g/mL) against the QRSA CCARM 3505 and 3519 strains. None of the compounds exhibited any activity against the Gram-negative bacteria Escherichia coli 1356 at 64 mu g/mL. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.023
• 作为产物：
  描述：

  2'-溴苯乙酮 在 对甲苯磺酸 、 1,3-二溴咪唑烷-2,4-二酮 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 8.0h， 生成 4-[2-(2-Bromophenyl)-2-oxoethoxy]benzaldehyde
  参考文献：
  名称：

  Synthesis and bioactivity evaluation of rhodanine derivatives as potential anti-bacterial agents

  摘要：

  Five series of (Z)-5-(4-(2-oxo-2-phenylethoxy)benzylidene)-2-thioxothiazolidin-4-one derivatives (I-V) were synthesized, characterized, and evaluated for their anti-bacterial activity. Most of the synthesized compounds showed potent inhibition against several Gram-positive bacteria (including multidrug-resistant clinical isolates) with MIC values in the range of 1-32 mu g/mL. Compounds IIIi, Vb and Vc presented the most potent activity, showing four-fold more potency than norfloxacin (MIC = 8 mu g/mL and 4 mu g/mL) and 64-fold more activity than oxacillin (MIC > 64 mu g/mL) against MRSA CCARM 3167 and 3506 strains with MIC values of 1 mu g/mL, and 64-fold more potency than norfloxacin (MIC > 64 mu g/mL) and comparable activity to oxacillin (MIC = 1 mu g/mL) against the QRSA CCARM 3505 and 3519 strains. None of the compounds exhibited any activity against the Gram-negative bacteria Escherichia coli 1356 at 64 mu g/mL. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.023