3-benzoyl-α-methylphenyl-acetic acid imidazolide | 78436-48-3

• 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: 3-benzoyl-α-methylphenyl-acetic acid imidazolide
• 英文别名: 2-(3-Benzoylphenyl)-1-imidazol-1-ylpropan-1-one
• CAS: 78436-48-3
• 化学式: C₁₉H₁₆N₂O₂
• 分子量: 304.348
• InChiKey: YPUXUAXWXUYMJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  52
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzoyl-α-methylphenyl-acetic acid imidazolide 、 2-[4-amino-3-bromo-5-(N-ethyl-cyclohexylaminomethyl)-benzoyloxy]-2'-hydroxydiethylsulfide 生成 2-[4-Amino-3-bromo-5-(N-ethyl-cyclohexylaminomethyl)-benzoyloxy]-2'-(3-benzoyl-α-methyl-phenyl-acetoxy)-diethylsulfide
  参考文献：
  名称：

  Esters and amides containing the

  摘要：

  公式##STR1##的化合物，其中每个X可以相同也可以不同于其他X，是氧或亚胺；R.sub.1是氢，氟，氯或溴；R.sub.2和R.sub.3，可以相同也可以相互不同，都是氢；未取代或单取代的1到6碳原子的烷基，其中取代基是苯基或1到3碳原子的二烷基氨基；吡啶基；或5到7碳原子的环烷基；R.sub.2和R.sub.3，与彼此以及它们所连接的氮原子一起，是吡咯烷基，哌啶基，己亚胺基，吗啉基，N-芳基哌嗪基或N-(1到3碳原子的烷基)哌嗪基；A是5到7碳原子的环烷基；未取代或取代的2到10碳原子的亚烷基，其中取代基是一到两个每个含有1到3碳原子的烷基，一到两个每个含有2到4碳原子的碳烷氧基，一到两个苯基，一到四个羟基，一个卤甲基，一个羟甲基，一个1到18碳原子的烷酰氧基，一个在烷酰基部分含有1到18碳原子的烷酰氧甲基或一个##STR2##其中R.sub.1，R.sub.2和R.sub.3具有先前定义的含义；或2到10碳原子的亚烷基，通过氧，硫，亚砜，磺酰基，苯基，环己基，吡啶基，哌嗪基或未取代或取代的亚胺基中断，其中亚胺基上的取代基是1到6碳原子的烷基，苯基或1到3碳原子的苯烷基；B是一种抗炎的羧酸的酰基残基；以及它们的非毒性，药理学上可接受的酸加成盐。这些化合物以及它们的盐可以用作抗炎药。

  公开号：

  US04362738A1
• 作为产物：
  描述：

  酮基布洛芬 、 N,N'-羰基二咪唑 以 氯仿 为溶剂， 反应 4.0h， 生成 3-benzoyl-α-methylphenyl-acetic acid imidazolide
  参考文献：
  名称：

  Chondroitin sulfate-based anti-inflammatory macromolecular prodrugs

  摘要：

  Macromolecular prodrugs of three non-steroidal anti-inflammatory drugs (NSAIDs), ibuprofen, ketoprofen, and naproxen, were prepared by the covalent attachment of the drugs onto chondroitin sulfate (ChS) using PEG 1000 as a spacer. Drug-PEG adducts were synthesized using 1,1'-carbonyl diimidazole as a coupling agent in dimethyl sulfoxide, followed by the reaction with ChS in highly dilute aqueous solution at pH 6.8 via N-(3-dimethylaminopropyl)N'-ethylcarbodiimide hydrochloride (EDAC) as a conjugation agent. The drug-ChS con confirmed by FTIR, H-1 NMR and C-13 NMR and the molar percent of drug substitution onto ChS was characterized by H-1 NMR using the peak areas of the three protons of -phi CHCH3 on the drugs to those of -NHCOCH3 on ChS. All drug-ChS conjugates are water-soluble. The release amounts of the free drugs from their corresponding drug-ChS conjugates were evaluated in the presence or absence of either esterase or chondroitinase, and the both enzymes in pH 7.4 Tris-buffer solutions at 37 degrees C by high performance liquid chromatography (HPLC). Keto-ChS conjugates. released similar to 100% ketoprofen within 12h in the presence of esterase, but the combination with chondroitinase did not accelerate the release rate. The degradation of Keto-ChS conjugates by chondroitinase was confirmed by gel permeation chromatography (GPC). The Keto-ChS conjugates still retained the enzymatic recognition even at the substitution of ketoprofen as high as 56 mol%. The inhibition percent of carrageenan-induced edema of Keto-ChS-56 was comparable to that of a simple blend of ChS and ketoprofen, suggesting that biologically active ChS and ketoprofen could be liberated from the conjugate. (c) 2006 Elsevier B.V.All rights reserved.

  DOI：

  10.1016/j.ejps.2006.05.010