2-(3-benzylphenyl)-N-(3-hydroxypropyl)propanamide

• 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: 2-(3-benzylphenyl)-N-(3-hydroxypropyl)propanamide
• 英文别名: fenoprofen 3-hydroxypropylamide
• 化学式: C₁₉H₂₃NO₂
• 分子量: 297.397
• InChiKey: MCUOKTYVHWFTIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-benzylphenyl)-N-(3-hydroxypropyl)propanamide 、 (((1S)-(4-chlorophenoxy)-(1-methyl)oxycarbonylethyl)amino)phosphinyl chloride 在 N-甲基咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以40%的产率得到
  参考文献：
  名称：

  The novel phosphoramidate derivatives of NSAID 3-hydroxypropylamides: Synthesis, cytostatic and antiviral activity evaluations

  摘要：

  The target phosphoramidates 5a-e were prepared in one step from 3-hydroxypropyl derivatives 3a-e of nonsteroidal anti-inflammatory drugs (fenoprofen, ketoprofen, ibuprofen, indomethacin, diclofenac). The products 3a-e and 5a-e were evaluated for their cytostatic and antiviral activity against malignant tumour cell lines and normal human fibroblasts (WI 38). All phosphoramidate derivatives 5a-e possess significantly greater inhibitory activities than the corresponding 3-hydroxypropyl derivatives 3a-e, whereby compound 5a showed the most potent inhibitory activities against cervical, pancreatic and colon carcinoma cell lines (IC50 = 5 - 7 mu M), (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.03.037
• 作为产物：
  描述：

  酮基布洛芬 在 10% palladium on activated charcoal 、 氢气 、 三乙胺 作用下， 以 甲醇 、 乙酸乙酯 、 甲苯 为溶剂， 反应 1.25h， 生成 2-(3-benzylphenyl)-N-(3-hydroxypropyl)propanamide
  参考文献：
  名称：

  The Novel Ketoprofen Amides - Synthesis and Biological Evaluation as Antioxidants, Lipoxygenase Inhibitors and Cytostatic Agents

  摘要：

  The novel amides of ketoprofen and its reduced derivatives (5a–f, 4a–n, 6a–g) with aromatic and cycloalkyl amines or hydroxylamines were prepared and screened for their reducing and cytostatic activity as well as for their ability to inhibit soybean lipoxygenase and lipid peroxidation. 1,1‐Diphenyl‐picrylhydrazyl test for reducing ability revealed that ketoprofen amides were more potent antioxidants than the amides of the reduced ketoprofen derivatives. The most active compound was benzhydryl ketoprofen amide 5f. Lipoxygenase inhibition of the tested compounds varied from strong to very weak. The most potent compound was benzhydryl derivative 6f (IC50 = 20.5 μm). Aromatic and cycloalkyl amides 4 and 5 were more potent lipoxygenase inhibitors than derivatives with carboxylic group. Aromatic amides of series 4 and 5 showed excellent lipid peroxidation inhibition (92.2–99.9%). On the other hand, the most pronounced cytostatic activity was exerted by O‐benzyl derivative 4i, although in general all tested reduced and non‐reduced lipophilic derivatives showed similar activity.

  DOI：

  10.1111/j.1747-0285.2010.00963.x

文献信息

• The novel phosphoramidate derivatives of NSAID 3-hydroxypropylamides: Synthesis, cytostatic and antiviral activity evaluations
  作者：K. Wittine、K. Benci、Z. Rajić、B. Zorc、M. Kralj、M. Marjanović、K. Pavelić、E. De Clercq、G. Andrei、R. Snoeck

  DOI：10.1016/j.ejmech.2008.03.037

  日期：2009.1

  The target phosphoramidates 5a-e were prepared in one step from 3-hydroxypropyl derivatives 3a-e of nonsteroidal anti-inflammatory drugs (fenoprofen, ketoprofen, ibuprofen, indomethacin, diclofenac). The products 3a-e and 5a-e were evaluated for their cytostatic and antiviral activity against malignant tumour cell lines and normal human fibroblasts (WI 38). All phosphoramidate derivatives 5a-e possess significantly greater inhibitory activities than the corresponding 3-hydroxypropyl derivatives 3a-e, whereby compound 5a showed the most potent inhibitory activities against cervical, pancreatic and colon carcinoma cell lines (IC50 = 5 - 7 mu M), (C) 2008 Elsevier Masson SAS. All rights reserved.
• The Novel Ketoprofen Amides - Synthesis and Biological Evaluation as Antioxidants, Lipoxygenase Inhibitors and Cytostatic Agents
  作者：Zrinka Rajić、Dimitra Hadjipavlou-Litina、Eleni Pontiki、Marijeta Kralj、Lidija Šuman、Branka Zorc

  DOI：10.1111/j.1747-0285.2010.00963.x

  日期：——

  The novel amides of ketoprofen and its reduced derivatives (5a–f, 4a–n, 6a–g) with aromatic and cycloalkyl amines or hydroxylamines were prepared and screened for their reducing and cytostatic activity as well as for their ability to inhibit soybean lipoxygenase and lipid peroxidation. 1,1‐Diphenyl‐picrylhydrazyl test for reducing ability revealed that ketoprofen amides were more potent antioxidants than the amides of the reduced ketoprofen derivatives. The most active compound was benzhydryl ketoprofen amide 5f. Lipoxygenase inhibition of the tested compounds varied from strong to very weak. The most potent compound was benzhydryl derivative 6f (IC50 = 20.5 μm). Aromatic and cycloalkyl amides 4 and 5 were more potent lipoxygenase inhibitors than derivatives with carboxylic group. Aromatic amides of series 4 and 5 showed excellent lipid peroxidation inhibition (92.2–99.9%). On the other hand, the most pronounced cytostatic activity was exerted by O‐benzyl derivative 4i, although in general all tested reduced and non‐reduced lipophilic derivatives showed similar activity.