(5E)-2-benzyl-5-[(4-methoxyphenyl)methylidene]cyclopentan-1-one | 183015-70-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (5E)-2-benzyl-5-[(4-methoxyphenyl)methylidene]cyclopentan-1-one
• CAS: 183015-70-5
• 化学式: C₂₀H₂₀O₂
• 分子量: 292.378
• InChiKey: DRXLGTNKSFFBGC-NBVRZTHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5E)-2-benzyl-5-[(4-methoxyphenyl)methylidene]cyclopentan-1-one 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 27.0h， 生成
  参考文献：
  名称：

  摘要：

  Purpose. A series of 2-substituted-2-dimethylaminomethyl-5-(E)-arylidene cyclopentanones, 4 were synthesized. The main objective of this investigation was to explore the structural parameters necessary for antiinflammatory activity in this series of compounds, while keeping cytotoxic action to a minimum.Methods. The target compounds were synthesized in two steps commencing with 2-alkyl-cyclopentanones. Antiinflammatory, analgesic and cytotoxic activities were determined in rats. Cytotoxic results were examined in human cell lines.Results. Eight of the eighteen synthetic substances possessed significant antiinflammatory activity and twelve showed appreciable analgesic action. Cytotoxicity was minimal or nonexistent for most of the compounds. The stability of one of the compounds, 4b in both aqueous and non-aqueous media, and an amine exchange reaction with aniline wee used to explain the observed antiinflammatory and cytotoxic activities.Conclusions. Unlike monosubstituted aminomethyl groups (Mannich bases) at the 2-position of 5-arylidene-2-cyclopentanones, a second substituent at the 2-position increases stability of the Mannich base and significantly decreases cytotoxic activity, Antiinflammatory and analgesic action is retained in many of the compounds, thus strongly indicating that these desired pharmacological results can be obtained without untoward damage to cells.

  DOI：

  10.1023/a:1016067210281
• 作为产物：
  描述：

  (5E)-2-benzyl-2-[(dimethylamino)methyl]-5-[(4-methoxyphenyl)methylidene]cyclopentan-1-one;hydrochloride 以 甲醇 为溶剂， 反应 12.0h， 以78%的产率得到(5E)-2-benzyl-5-[(4-methoxyphenyl)methylidene]cyclopentan-1-one
  参考文献：
  名称：

  摘要：

  Purpose. A series of 2-substituted-2-dimethylaminomethyl-5-(E)-arylidene cyclopentanones, 4 were synthesized. The main objective of this investigation was to explore the structural parameters necessary for antiinflammatory activity in this series of compounds, while keeping cytotoxic action to a minimum.Methods. The target compounds were synthesized in two steps commencing with 2-alkyl-cyclopentanones. Antiinflammatory, analgesic and cytotoxic activities were determined in rats. Cytotoxic results were examined in human cell lines.Results. Eight of the eighteen synthetic substances possessed significant antiinflammatory activity and twelve showed appreciable analgesic action. Cytotoxicity was minimal or nonexistent for most of the compounds. The stability of one of the compounds, 4b in both aqueous and non-aqueous media, and an amine exchange reaction with aniline wee used to explain the observed antiinflammatory and cytotoxic activities.Conclusions. Unlike monosubstituted aminomethyl groups (Mannich bases) at the 2-position of 5-arylidene-2-cyclopentanones, a second substituent at the 2-position increases stability of the Mannich base and significantly decreases cytotoxic activity, Antiinflammatory and analgesic action is retained in many of the compounds, thus strongly indicating that these desired pharmacological results can be obtained without untoward damage to cells.

  DOI：

  10.1023/a:1016067210281

文献信息

• ——
  作者：Haitao Chen、Zhizhong Ji、Lan K. Wong、Jerome F. Siuda、Ven L. Narayanan

  DOI：10.1023/a:1016067210281

  日期：——

  Purpose. A series of 2-substituted-2-dimethylaminomethyl-5-(E)-arylidene cyclopentanones, 4 were synthesized. The main objective of this investigation was to explore the structural parameters necessary for antiinflammatory activity in this series of compounds, while keeping cytotoxic action to a minimum.Methods. The target compounds were synthesized in two steps commencing with 2-alkyl-cyclopentanones. Antiinflammatory, analgesic and cytotoxic activities were determined in rats. Cytotoxic results were examined in human cell lines.Results. Eight of the eighteen synthetic substances possessed significant antiinflammatory activity and twelve showed appreciable analgesic action. Cytotoxicity was minimal or nonexistent for most of the compounds. The stability of one of the compounds, 4b in both aqueous and non-aqueous media, and an amine exchange reaction with aniline wee used to explain the observed antiinflammatory and cytotoxic activities.Conclusions. Unlike monosubstituted aminomethyl groups (Mannich bases) at the 2-position of 5-arylidene-2-cyclopentanones, a second substituent at the 2-position increases stability of the Mannich base and significantly decreases cytotoxic activity, Antiinflammatory and analgesic action is retained in many of the compounds, thus strongly indicating that these desired pharmacological results can be obtained without untoward damage to cells.