N-(4-hydroxyphenyl)-4-chlorobutyrylamide

• 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-(4-hydroxyphenyl)-4-chlorobutyrylamide
• 英文别名: 4-chloro-N-(4-hydroxyphenyl)butanamide
• 化学式: C₁₀H₁₂ClNO₂
• 分子量: 213.664
• InChiKey: JRRMKKQFQOQDGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  N-(4-hydroxyphenyl)-4-chlorobutyrylamide 、 saccharin sodium salt 在 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以82%的产率得到N-(4-hydroxyphenyl)-4-(1,1,3-trioxo-1,2-benzothiazol-2-yl)butanamide
  参考文献：
  名称：

  Synthesis and in vivo evaluation of non-hepatotoxic acetaminophen analogs

  摘要：

  A series of acetaminophen (APAP) analogs, 2-(1,1-dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl)-N-(4-hydroxyphenyl)alkanecarboxamides, bearing a heterocyclic moiety linked to the p-acylaminophenol fragment, were prepared in a general project to develop APAP analogs with modulated pharmacokinetic profiles. Unexpectedly, the products described maintained the in vivo analgesic profile, while the characteristic hepatotoxicity of APAP was consistently reduced. One of the products, 5a, was studied in vivo in comparison with APAP. Compound 5a displayed an analgesic efficacy comparable to that of APAP. A relatively high acute oral dose of 5a (6 mmol/kg) produced no measurable toxicity, whereas the equimolar dose of APAP increased transaminase activity, depleted hepatic and renal glutathione, and resulted in mortality. In human hepatocytes (HEPG-2) and in human primary cultures of normal liver cells, APAP, but not 5a, was associated with apoptotic cell death, Fas-ligand up-regulation, and CAR (constitutive androstane receptor) activation, contributing to a favorable safety profile of 5a as an orally delivered analgesic. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.054
• 作为产物：
  描述：

  对氨基苯酚 、 4-氯丁酰氯 在 sodium acetate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.0h， 以56%的产率得到N-(4-hydroxyphenyl)-4-chlorobutyrylamide
  参考文献：
  名称：

  Synthesis and in vivo evaluation of non-hepatotoxic acetaminophen analogs

  摘要：

  A series of acetaminophen (APAP) analogs, 2-(1,1-dioxido-3-oxo-1,2-benzisothiazol-2(3H)-yl)-N-(4-hydroxyphenyl)alkanecarboxamides, bearing a heterocyclic moiety linked to the p-acylaminophenol fragment, were prepared in a general project to develop APAP analogs with modulated pharmacokinetic profiles. Unexpectedly, the products described maintained the in vivo analgesic profile, while the characteristic hepatotoxicity of APAP was consistently reduced. One of the products, 5a, was studied in vivo in comparison with APAP. Compound 5a displayed an analgesic efficacy comparable to that of APAP. A relatively high acute oral dose of 5a (6 mmol/kg) produced no measurable toxicity, whereas the equimolar dose of APAP increased transaminase activity, depleted hepatic and renal glutathione, and resulted in mortality. In human hepatocytes (HEPG-2) and in human primary cultures of normal liver cells, APAP, but not 5a, was associated with apoptotic cell death, Fas-ligand up-regulation, and CAR (constitutive androstane receptor) activation, contributing to a favorable safety profile of 5a as an orally delivered analgesic. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.07.054

文献信息

• High-fluidity polycarbonates and process for preparing them
  申请人：ENICHEM S.p.A.

  公开号：EP0409312A2

  公开（公告）日：1991-01-23

  Linear, thermoplastic, aromatic polycarbonates having an average viscosimetric molecular weight comprised within the range of from 10,000 to 30,000, endowed with high fluidity in the molten state, are obtained by means of the use of chain capping agents of phenol-amidic nature, having the general formula: wherein: R, R₁, which can be either equal to, or different from, each other, are H or CH₃; R₂ is an either linear or branched alkyl radical, containing from 1 to 7 carbon atoms, or a cycloalkyl or alkylene-cycloalkyl radical of from 5 to 7 carbon atoms, with said alkyl, cycloalkyl or alkylene-cycloalkyl radicals possibly bearing a halogen atom.

  线性、热塑性、芳香族聚碳酸酯的平均粘度分子量在 10,000 至 30,000 之间，在熔融状态下具有高流动性，可通过使用具有通式的苯酚-氨基性质的链封端剂获得： 其中 R、R₁ 可以是 H 或 CH₃，也可以互不相同； R₂ 是含有 1 至 7 个碳原子的直链或支链烷基，或含有 5 至 7 个碳原子的环烷基或亚烷基环烷基，所述烷基、环烷基或亚烷基环烷基可能含有卤素原子。