N-(3-hydroxypropyl)ketoprofenamide | 737776-65-7

• 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: N-(3-hydroxypropyl)ketoprofenamide
• 英文别名: ketoprofen 3-hydroxypropylamide；2-(3-benzoylphenyl)-N-(3-hydroxypropyl)propanamide
• CAS: 737776-65-7
• 化学式: C₁₉H₂₁NO₃
• 分子量: 311.381
• InChiKey: KAHABLZRPCUAHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (((1S)-(4-chlorophenoxy)-(1-methyl)oxycarbonylethyl)amino)phosphinyl chloride 、 N-(3-hydroxypropyl)ketoprofenamide 在 N-甲基咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以55%的产率得到C₂₉H₃₂ClN₂O₇P
  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：

  3-氨基-1-丙醇 、 ketoprofen benzotriazolide 在 三乙胺 作用下， 生成 N-(3-hydroxypropyl)ketoprofenamide
  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

文献信息

• Zovko, Marijana; Zorc, Branka; Takac, Milena Jadrijevic-Mladar, Croatica Chemica Acta, 2003, vol. 76, # 4, p. 335 - 341
  作者：Zovko, Marijana、Zorc, Branka、Takac, Milena Jadrijevic-Mladar、Metelko, Biserka、Novak, Predrag

  DOI：——

  日期：——
• 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.