N-cyclohexylketoprofenamide

• 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-cyclohexylketoprofenamide
• 英文别名: 2-(3-benzoylphenyl)-N-cyclohexylpropanamide；N-cyclohexyl-2-[3-(phenylcarbonyl)phenyl]propanamide
• 化学式: C₂₂H₂₅NO₂
• 分子量: 335.446
• InChiKey: DDHROCVILJJVFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-cyclohexylketoprofenamide 在 Pd/C(en) 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 以75%的产率得到N-cyclohexyl-2-(3-(hydroxy(phenyl)methyl)phenyl)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
• 作为产物：
  描述：

  酮基布洛芬 在 三乙胺 作用下， 以 甲苯 为溶剂， 生成 N-cyclohexylketoprofenamide
  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

• [EN] 2-ARYL-PROPIONAMIDE DERIVATIVES USEFUL AS BRADYKININ RECEPTOR ANTAGONISTS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] DÉRIVÉS DE 1-ARYL-PROPIONAMIDE UTILES COMME ANTAGONISTES DES RÉCEPTEURS DE LA BRADYKININE ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：DOMPE SPA

  公开号：WO2011051375A1

  公开（公告）日：2011-05-05

  (R,S) 2-aryl-propionamide derivatives, or their single enantiomers (R) and (S) are disclosed useful in the treatment or prevention of symptoms and disorders such as pain and inflammation associated with the bradykinin B1 pathway.

  (R,S) 2-芳基丙酰胺衍生物，或其单对映体(R)和(S)，被披露用于治疗或预防与布雷金肽B1途径相关的症状和疾病，如疼痛和炎症。
• 2-aryl-propionamide derivatives useful as bradykinin receptor antagonists and pharmaceutical compositions containing them
  申请人：Dompe S.p.A.

  公开号：EP2316820A1

  公开（公告）日：2011-05-04

  (R,S) 2-aryl-propionamide derivatives, or their single enantiomers (R) and (S) are disclosed useful in the treatment or prevention of symptoms and disorders such as pain and inflammation associated with the bradykinin B1 pathway.

  (R,S) 2-芳基丙酰胺衍生物，或其单对映体(R)和(S)，被披露为在治疗或预防与布雷金肽B1通路相关的疼痛和炎症症状和疾病中有用。
• 2-ARYL-PROPIONAMIDE DERIVATIVES USEFUL AS BRADYKININ RECEPTOR ANTAGONISTS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：Beccari Andrea

  公开号：US20120316169A1

  公开（公告）日：2012-12-13

  (R,S) 2-aryl-propionamide derivatives, or their single enantiomers (R) and (S) are disclosed useful in the treatment or prevention of symptoms and disorders such as pain and inflammation associated with the bradykinin B1 pathway.

  本文披露了(R,S) 2-芳基丙酰胺衍生物，或其单一对映体(R)和(S)，适用于治疗或预防与布雷金肽B1途径相关的疼痛和炎症等症状和疾病。
• Efficient catalyst-free direct amidation of non-activated carboxylic acids from carbodiimides
  作者：Mehmet Mart、Janusz Jurczak、Idris Karakaya

  DOI：10.1039/d2ob01322c

  日期：——

  A novel and efficient catalyst- and activating agent-free amidation method via direct amidation of carboxylic acids where carbodiimides act as a reagent instead of an activating agent is reported. The reaction is conducted under non-traditional coupling conditions where a higher temperature is employed. Besides not using stoichiometric ratios of activating agent or catalyst, this approach is made even

  报道了一种通过羧酸直接酰胺化的新型有效的无催化剂和活化剂酰胺化方法，其中碳二亚胺作为试剂而不是活化剂。该反应在使用更高温度的非传统偶联条件下进行。除了不使用化学计量比的活化剂或催化剂外，这种方法在环境友好且可回收的无毒溶剂 DMSO 的存在下变得更具吸引力。种类繁多的苄基、脂肪族、α,β-不饱和和芳香族羧酸以高达 95% 的产率提供相关的酰胺。克级反应的优异产率表明，该应用对于大规模合成应用特别方便。
• 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：——