2-(3-benzoylphenyl)propanehydrazide | 1073126-84-7

• 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: 2-(3-benzoylphenyl)propanehydrazide
• CAS: 1073126-84-7
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: XLMRDXXNLWHKSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-benzoylphenyl)propanehydrazide 在 sodium ethanolate 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 16.0h， 生成 3-[2-{5-(1-(3-benzoylphenyl)ethyl)-1,3,4-oxadiazol-2-ylthio}acetyl]-2H-chromen-2-one
  参考文献：
  名称：

  3-[（5-取代-1,3,4-恶二唑-2-基-硫基）乙酰基] -2H-铬-2-酮的合成及抗炎和镇痛活性的评价

  摘要：

  通过适当取代基之间的缩合反应合成了一系列新的3-[（5-取代-1,3,4-恶二唑-2-基-硫基）乙酰基] -2H-铬-2--2-酮（7a – i）。来自多种现有NSAID的5-取代的1,3,4-恶二唑基-2-硫酮（4a – i）和3-（2-溴乙酰基）-2H-铬-2--2-酮（6）在存在下回流下乙醇钠。根据理化，元素分析和光谱数据确定了合成化合物的结构。以200mg / kg体重的剂量筛选标题化合物的体内急性抗炎和镇痛活性。在该系列中，四种化合物7c，7e，7f发现7h和7h具有明显的抗炎和镇痛活性。另外，与标准的NSAID相比，还发现这些化合物具有较小程度的致溃疡潜力。

  DOI：

  10.1007/s00044-010-9494-z
• 作为产物：
  描述：

  酮基布洛芬 在 hydrazine hydrate 、 硫酸 作用下， 以 乙醇 为溶剂， 生成 2-(3-benzoylphenyl)propanehydrazide
  参考文献：
  名称：

  3-[（5-取代-1,3,4-恶二唑-2-基-硫基）乙酰基] -2H-铬-2-酮的合成及抗炎和镇痛活性的评价

  摘要：

  通过适当取代基之间的缩合反应合成了一系列新的3-[（5-取代-1,3,4-恶二唑-2-基-硫基）乙酰基] -2H-铬-2--2-酮（7a – i）。来自多种现有NSAID的5-取代的1,3,4-恶二唑基-2-硫酮（4a – i）和3-（2-溴乙酰基）-2H-铬-2--2-酮（6）在存在下回流下乙醇钠。根据理化，元素分析和光谱数据确定了合成化合物的结构。以200mg / kg体重的剂量筛选标题化合物的体内急性抗炎和镇痛活性。在该系列中，四种化合物7c，7e，7f发现7h和7h具有明显的抗炎和镇痛活性。另外，与标准的NSAID相比，还发现这些化合物具有较小程度的致溃疡潜力。

  DOI：

  10.1007/s00044-010-9494-z

文献信息

• Fabrication of organogels achieved by prodrug-based organogelators of ketoprofen
  作者：Rahul R. Mahire、Deepika S. Agrawal、Devanand K. Patil、Dhananjay H. More

  DOI：10.1039/c4ra03688c

  日期：——

  The treatment strategy of curing diseases using prodrugs of an anti-inflammatory drug is widespread. In the present study, we report on the synthesis of prodrugs of ketoprofen, consisting of a derivatization of ketoprofen and long hydrocarbon chain of fatty acids with diacylhydrazine linkage. The presence of an acidic moiety in ketoprofen may lead to ulceration in the gastrointestinal tract that reduces the efficacy of the drug with an increased adverse effect. The synthesis of prodrugs of ketoprofen involves the use of fatty acids as a carrier and hydrazine as a spacer. Synthesized prodrugs were characterized by infrared, 1H-NMR and mass spectroscopy. The resulting prodrugs were found to be insoluble in water and precipitated out in acetonitrile, hexane, benzene, and so on. The synthesized prodrugs are slightly soluble in chloroform, methanol and ethanol and only form a gel like structure in carbon tetrachloride. The resulting gels are referred as organogels and prodrugs are referred to as organogelators. The surface morphology of the prepared organogels were studied by field emission-scanning electron microscopy (FE-SEM) and transmission electron microscopy (TEM), and other spectral characteristics were also investigated. FE-SEM and TEM images revealed that there were continuous elongated fiber-like structures present that were in the nanometer size range. Gel–sol temperature profiles of the prepared organogels were also studied using differential scanning calorimetry. The results from all these techniques are presented and discussed from point of view of the use of the derivatives as prodrug formulations. It is demonstrated that the prodrug containing the diacylhydrazine moiety has the ability to form a gel.

  利用抗炎药物的前药治疗疾病的策略应用广泛。在本研究中，我们报道了酮洛芬前药的合成，该前药由酮洛芬的衍生化和具有二酰肼键的长碳链脂肪酸组成。酮洛芬中的酸性基团可能导致胃肠道溃疡，这种副作用减少了药物的有效性并增加了不良反应。酮洛芬前药的合成采用了脂肪酸作为载体和肼作为间隔物。合成的前药通过红外、核磁共振和质谱法进行了特征表征。结果显示，这些前药不溶于水，并在乙腈、己烷、苯等溶剂中沉淀出来。它们在氯仿、甲醇和乙醇中略溶，并且仅在四氯化碳中形成凝胶状结构。这些形成的凝胶被称为有机凝胶，前药被称为有机凝胶形成剂。通过场发射扫描电子显微镜（FE-SEM）和透射电子显微镜（TEM）研究了制备的有机凝胶的表面形态，并调查了其他光谱特性。FE-SEM和TEM图像显示存在连续的纳米级长纤维状结构。还使用差示扫描量热法研究了制备的有机凝胶的凝胶-溶胶温度曲线。从使用这些衍生物作为前药配方的角度出发，展示了所有这些技术的结果并进行了讨论。结果表明，含有二酰肼结构的前药具有形成凝胶的能力。
• PHTHALIMIDE DERIVATIVES OF NON-STEROIDAL ANTI-INFLAMMATORY COMPOUNDS AND/OR TNF-ALPHA MODULATORS, METHOD FOR PRODUCING SAME, PHARMACEUTICAL COMPOSITIONS CONTAINING SAME AND USES THEREOF FOR THE TREATMENT OF INFLAMMATORY DISEASES
  申请人：dos Santos Jean Leandro

  公开号：US20120115817A1

  公开（公告）日：2012-05-10

  The present invention relates to phthalimide derivatives of non-steroidal and/or TNF-α modulating anti-inflammatory compounds as well as the process of obtaining the so-called derivatives, pharmaceutical compositions containing such derivatives and their uses, including use in the treatment of inflammatory diseases, especially those related to chronic inflammatory processes, such as rheumatoid arthritis and intestinal inflammatory diseases (for instance, Chron's disease) and the use of the referred to pharmaceutical compositions as antipyretic, analgesic and platelet antiaggregating medications.

  本发明涉及非甾体和/或调节肿瘤坏死因子-α（TNF-α）的抗炎化合物的酞酰亚胺衍生物，以及获得所述衍生物的方法、包含该衍生物的药物组合物及其用途，包括用于治疗炎症疾病，尤其是与慢性炎症过程相关的疾病，例如类风湿性关节炎和肠道炎症疾病（例如，克罗恩病），以及将所述药物组合物用作退热剂、镇痛剂和抗血小板聚集药物的使用。
• PHTHALIMIDE DERIVATIVES OF NON-STEROIDAL ANTI-INFLAMMATORY COMPOUNDS AND/OR TNF- MODULATORS, METHOD FOR PRODUCING SAME, PHARMACEUTICAL COMPOSITIONS CONTAINING SAME AND USES THEREOF FOR THE TREATMENT OF INFLAMMATORY DISEASES
  申请人：EMS S. A.

  公开号：EP2418200A1

  公开（公告）日：2012-02-15

  The present invention relates to phthalimide derivatives of non-steroidal and/or TNF-α modulating anti-inflammatory compounds as well as the process of obtaining the so-called derivatives, pharmaceutical compositions containing such derivatives and their uses, including use in the treatment of inflammatory diseases, especially those related to chronic inflammatory processes, such as rheumatoid arthritis and intestinal inflammatory diseases (for instance, Chron's disease) and the use of the referred to pharmaceutical compositions as antipyretic, analgesic and platelet antiaggregating medications.

  本发明涉及非甾体类和/或 TNF-α 调节抗炎化合物的邻苯二甲酰亚胺衍生物，以及获得所谓衍生物的工艺、含有此类衍生物的药物组合物及其用途，包括用于治疗炎症性疾病，尤其是与慢性炎症过程有关的疾病，如类风湿性关节炎和肠道炎症性疾病（如慢性疾病），以及将所述药物组合物用作解热、镇痛和抗血小板聚集药物。
• EP2418200
  申请人：——

  公开号：——

  公开（公告）日：——
• Parcha, Versha; Kaur, Jaswinder; Gupta, Vinay, Journal of the Indian Chemical Society, 2008, vol. 85, # 3, p. 321 - 325
  作者：Parcha, Versha、Kaur, Jaswinder、Gupta, Vinay、Anroop

  DOI：——

  日期：——