N-Benzyl-2-[1-(4-chloro-phenyl)-meth-(E)-ylidene]-4-oxo-4-(4-phenoxy-phenyl)-butyramide | 1027257-45-9

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: N-Benzyl-2-[1-(4-chloro-phenyl)-meth-(E)-ylidene]-4-oxo-4-(4-phenoxy-phenyl)-butyramide
• 英文别名: (2E)-N-benzyl-2-[(4-chlorophenyl)methylidene]-4-oxo-4-(4-phenoxyphenyl)butanamide
• CAS: 1027257-45-9
• 化学式: C₃₀H₂₄ClNO₃
• 分子量: 481.978
• InChiKey: VLZZJLTYCBPUEH-NCELDCMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-Benzyl-2-[1-(4-chloro-phenyl)-meth-(E)-ylidene]-4-oxo-4-(4-phenoxy-phenyl)-butyramide 在 盐酸 作用下， 反应 1.0h， 生成 1-Benzyl-3-[1-(4-chloro-phenyl)-meth-(E)-ylidene]-5-(4-phenoxy-phenyl)-1,3-dihydro-pyrrol-2-one
  参考文献：
  名称：

  2-Arylidene-4-(4-phenoxy-phenyl)but-3-en-4-olides: Synthesis, reactions and biological activity

  摘要：

  2-Arylidene-4-(4-phenoxy-phenyl)but-3-en-4-olides (1-17) were prepared from 3-(4-phenoxy-benzoyl)propionic acid and aromatic aldehydes. Some of the selected butenolides were reacted with ammonia and benzylamine to give corresponding 3-arylidene-5-(4-phenoxyphenyl)-2(3H)-pyrrolones (18-23) and 3-arylidene-5-(4-phenoxy-phenyl)-1-benzyl-2(3H)-pyrrolones (24-29) respectively, which were characterized on the basis of H-1-, C-13-NMR, Mass spectrometric data and elemental analysis results. These compounds were tested for antiinflammatory and antimicrobial actions. The compounds, which showed significant anti-inflammatory activity, were screened for their analgesic and ulcerogenic activities. Five new compounds (5, 6, 7, 25 and 26), out of 29 showed very good anti-inflammatory activity in the carrageenan induced rat paw edema test, with significant analgesic activity in the acetic acid induced writhing test together with negligible ulcerogenic action. Antibacterial activity against Staphylococcus aureus and Escherichia coli as well as antifungal activity against Candida albicans were expressed as the corresponding minimum inhibitory concentration (MIC) values. Compound 21, 22 and 23 showed excellent activity against C. albicans with MIC-10 mu g/ml. Out of the above-mentioned compounds, 22 and 23 also showed good activity against S. aureus with MIC-20 and 15 mu g/ml respectively. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.03.012
• 作为产物：
  描述：

  gamma-氧代-4-苯氧基-苯丁酸 在 乙酸酐 、 三乙胺 作用下， 以 苯 为溶剂， 反应 6.0h， 生成 N-Benzyl-2-[1-(4-chloro-phenyl)-meth-(E)-ylidene]-4-oxo-4-(4-phenoxy-phenyl)-butyramide
  参考文献：
  名称：

  2-Arylidene-4-(4-phenoxy-phenyl)but-3-en-4-olides: Synthesis, reactions and biological activity

  摘要：

  2-Arylidene-4-(4-phenoxy-phenyl)but-3-en-4-olides (1-17) were prepared from 3-(4-phenoxy-benzoyl)propionic acid and aromatic aldehydes. Some of the selected butenolides were reacted with ammonia and benzylamine to give corresponding 3-arylidene-5-(4-phenoxyphenyl)-2(3H)-pyrrolones (18-23) and 3-arylidene-5-(4-phenoxy-phenyl)-1-benzyl-2(3H)-pyrrolones (24-29) respectively, which were characterized on the basis of H-1-, C-13-NMR, Mass spectrometric data and elemental analysis results. These compounds were tested for antiinflammatory and antimicrobial actions. The compounds, which showed significant anti-inflammatory activity, were screened for their analgesic and ulcerogenic activities. Five new compounds (5, 6, 7, 25 and 26), out of 29 showed very good anti-inflammatory activity in the carrageenan induced rat paw edema test, with significant analgesic activity in the acetic acid induced writhing test together with negligible ulcerogenic action. Antibacterial activity against Staphylococcus aureus and Escherichia coli as well as antifungal activity against Candida albicans were expressed as the corresponding minimum inhibitory concentration (MIC) values. Compound 21, 22 and 23 showed excellent activity against C. albicans with MIC-10 mu g/ml. Out of the above-mentioned compounds, 22 and 23 also showed good activity against S. aureus with MIC-20 and 15 mu g/ml respectively. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.03.012

文献信息

• 2-Arylidene-4-(4-phenoxy-phenyl)but-3-en-4-olides: Synthesis, reactions and biological activity
  作者：Asif Husain、M.S.Y. Khan、S.M. Hasan、M.M. Alam

  DOI：10.1016/j.ejmech.2005.03.012

  日期：2005.12

  2-Arylidene-4-(4-phenoxy-phenyl)but-3-en-4-olides (1-17) were prepared from 3-(4-phenoxy-benzoyl)propionic acid and aromatic aldehydes. Some of the selected butenolides were reacted with ammonia and benzylamine to give corresponding 3-arylidene-5-(4-phenoxyphenyl)-2(3H)-pyrrolones (18-23) and 3-arylidene-5-(4-phenoxy-phenyl)-1-benzyl-2(3H)-pyrrolones (24-29) respectively, which were characterized on the basis of H-1-, C-13-NMR, Mass spectrometric data and elemental analysis results. These compounds were tested for antiinflammatory and antimicrobial actions. The compounds, which showed significant anti-inflammatory activity, were screened for their analgesic and ulcerogenic activities. Five new compounds (5, 6, 7, 25 and 26), out of 29 showed very good anti-inflammatory activity in the carrageenan induced rat paw edema test, with significant analgesic activity in the acetic acid induced writhing test together with negligible ulcerogenic action. Antibacterial activity against Staphylococcus aureus and Escherichia coli as well as antifungal activity against Candida albicans were expressed as the corresponding minimum inhibitory concentration (MIC) values. Compound 21, 22 and 23 showed excellent activity against C. albicans with MIC-10 mu g/ml. Out of the above-mentioned compounds, 22 and 23 also showed good activity against S. aureus with MIC-20 and 15 mu g/ml respectively. (c) 2005 Elsevier SAS. All rights reserved.