5-benzoyl-N-(4-hydroxyphenyl)-2,3-dihydro-1H-pyrrolizine-1-carboxamide | 916165-56-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-benzoyl-N-(4-hydroxyphenyl)-2,3-dihydro-1H-pyrrolizine-1-carboxamide
• CAS: 916165-56-5
• 化学式: C₂₁H₁₈N₂O₃
• 分子量: 346.386
• InChiKey: XHMJWUCKCBDJSZ-UHFFFAOYSA-N

物化性质

• 熔点：
  228-229 °C(Solv: acetone (67-64-1); ligroine (8032-32-4))
• 沸点：
  651.4±55.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  71.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-benzoyl-N-(4-hydroxyphenyl)-2,3-dihydro-1H-pyrrolizine-1-carboxamide 、 乙酸酐 在 吡啶 作用下， 反应 3.0h， 以89%的产率得到
  参考文献：
  名称：

  Synthesis of new chemical entities from paracetamol and NSAIDs with improved pharmacodynamic profile

  摘要：

  It was envisaged to-combine high antipyretic activity of paracetamol into commonly used NSAIDs. To achieve this goal new chemical entities were synthesized by chemically combining paracetamol and NSAIDs, and biologically evaluated for their antipyretic, analgesic, anti-inflammatory and ulcerogenic potential. The acid chloride of parent NSAIDs was reacted with excess of p-aminophenol to yield the desired p-amidophenol derivatives (1B-7B). Acetate derivatives (1C-7C) of these phenols (1B-7B) were also prepared by their treatment with acetic anhydride, in order to see the impact of blocking the free phenolic group on the biological activity of the derivatives. All the synthesized p-amidophenol derivatives showed improved antipyretic activity than paracetamol with retention of anti-inflammatory activity of their parent NSAIDs. These compounds elicited no ulcerogenicity unlike their parent drugs. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.08.017
• 作为产物：
  描述：

  酮咯酸 在 氯化亚砜 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 6.0h， 生成 5-benzoyl-N-(4-hydroxyphenyl)-2,3-dihydro-1H-pyrrolizine-1-carboxamide
  参考文献：
  名称：

  Synthesis of new chemical entities from paracetamol and NSAIDs with improved pharmacodynamic profile

  摘要：

  It was envisaged to-combine high antipyretic activity of paracetamol into commonly used NSAIDs. To achieve this goal new chemical entities were synthesized by chemically combining paracetamol and NSAIDs, and biologically evaluated for their antipyretic, analgesic, anti-inflammatory and ulcerogenic potential. The acid chloride of parent NSAIDs was reacted with excess of p-aminophenol to yield the desired p-amidophenol derivatives (1B-7B). Acetate derivatives (1C-7C) of these phenols (1B-7B) were also prepared by their treatment with acetic anhydride, in order to see the impact of blocking the free phenolic group on the biological activity of the derivatives. All the synthesized p-amidophenol derivatives showed improved antipyretic activity than paracetamol with retention of anti-inflammatory activity of their parent NSAIDs. These compounds elicited no ulcerogenicity unlike their parent drugs. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.08.017

文献信息

• Synthesis of new chemical entities from paracetamol and NSAIDs with improved pharmacodynamic profile
  作者：Mange Ram Yadav、Datta M. Nimekar、A. Ananthakrishnan、Pathik S. Brahmkshatriya、Shrikant T. Shirude、Rajani Giridhar、Arvind Parmar、R. Balaraman

  DOI：10.1016/j.bmc.2006.08.017

  日期：2006.12

  It was envisaged to-combine high antipyretic activity of paracetamol into commonly used NSAIDs. To achieve this goal new chemical entities were synthesized by chemically combining paracetamol and NSAIDs, and biologically evaluated for their antipyretic, analgesic, anti-inflammatory and ulcerogenic potential. The acid chloride of parent NSAIDs was reacted with excess of p-aminophenol to yield the desired p-amidophenol derivatives (1B-7B). Acetate derivatives (1C-7C) of these phenols (1B-7B) were also prepared by their treatment with acetic anhydride, in order to see the impact of blocking the free phenolic group on the biological activity of the derivatives. All the synthesized p-amidophenol derivatives showed improved antipyretic activity than paracetamol with retention of anti-inflammatory activity of their parent NSAIDs. These compounds elicited no ulcerogenicity unlike their parent drugs. (c) 2006 Elsevier Ltd. All rights reserved.