N-(3,5-二氟-4-羟基苯基)-乙酰胺 | 151414-41-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(3,5-二氟-4-羟基苯基)-乙酰胺
• 英文名称: 3,5-difluoro-4-hydroxyacetanilide
• 英文别名: N-(3,5-difluoro-4-hydroxyphenyl)acetamide
• CAS: 151414-41-4
• 化学式: C₈H₇F₂NO₂
• 分子量: 187.146
• InChiKey: FNGKYBRZEZRPTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3,5-二氟-4-羟基苯基)-乙酰胺 在 silver(l) oxide 作用下， 以 氘代氯仿 为溶剂， 反应 15.0h， 以85%的产率得到N-(3,5-Difluoro-4-oxo-cyclohexa-2,5-dienylidene)-acetamide
  参考文献：
  名称：

  Rat liver microsomal cytochrome P450-dependent oxidation of 3,5-disubstituted analogues of paracetamol

  摘要：

  1. The cytochrome P450-dependent binding of paracetamol and a series of 3,5-disubstituted paracetamol analogues (R = -F, -Cl, -Br, -I, -CH3, -C2H5, -iC(3)H(7)) have been determined with beta-naphthoflavone (beta NF)-induced rat liver microsomes and produced reverse type I spectral changes. K-s,K-app varied from 0.14 mM for 3,5-diiC(3)H(7)-paracetamol to 2.8 mM for paracetamol.2. All seven analogues underwent rat liver microsomal cytochrome P450-dependent oxidation, as reflected by the formation of GSSG in the presence of GSH. The GSSG-formation was increased in all cases upon pretreatment of rats by beta-naphthoflavone (beta NF) and was generally decreased upon pretreatment by phenobarbital (PB).3. Rat liver microsomal cytochrome P450 as well as horseradish peroxidase catalysed the formation of 3,5-disubstituted NAPQI analogues from the corresponding parent compounds, as identified by UV-spectrophotometry of the NAPQI analogues and by GC/MS detection of the following GSH-conjugates: 2-glutathione-S-yl-3,5-dimethyl-1,4-dihydroxybenzene, 2-glutathione-S-yl-3,5-dichloro-paracetamol, and 2-glutathione-S-yl-3,5-dibromo-paracetamol.4. In liver microsomal (beta NF-induced) incubations, apparent K,values, as determined for the cytochrome P450 catalysis-dependent oxidation of GSH, for seven 3,5-disubstituted paracetamol analogues (R = -F, -Cl, -Br, -I, -CH3, -C2H5, iC(3)H(7)) varied from 0.07 to 0.64 mM. Paracetamol exhibited an apparent K-m of 0.73 mM. Apparent V-max values for the cytochrome P450 catalysis dependent oxidation of GSH varied from 0.66 nmol min(-1) mg(-1)protein for paracetamol to 3.0 nmol min(-1) mg(-1) protein for 3,5-dimethyl-paracetamol.

  DOI：

  10.3109/00498259609046740
• 作为产物：
  描述：

  2,6-二氟苯酚 在 palladium on activated charcoal 、 硫酸 、 硝酸 、 ammonium formate 、 三溴化硼 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.67h， 生成 N-(3,5-二氟-4-羟基苯基)-乙酰胺
  参考文献：
  名称：

  氟取代对扑热息痛的理化性质和止痛活性的影响。

  摘要：

  研究了6-羟基乙酰苯胺（对乙酰氨基酚）的六个氟化类似物的理化性质和止痛作用。与羟基相邻的氟取代增加了亲脂性和氧化电位，而与酰胺相邻的取代对亲脂性的影响很小，但导致氧化电位的增加更大。对于在2和6位具有氟的类似物，也缺乏酰胺基团和芳环的共平面性和共轭性。将氟引入对乙酰氨基酚的酰胺基团使亲脂性提高了4倍，并且还提高了对乙酰氨基酚的氧化电位。在苯醌诱导的雄性瑞士白老鼠的腹部收缩试验中，ED50的镇痛活性值表明，氟取代环可降低活性，特别是在2,6位 将氟引入酰胺基团显着增强了活性。镇痛作用与理化性质的关系表明，酰胺基团与芳环的共轭（和平面性）对于活性至关重要，并且容易氧化也可能是重要的因素。

  DOI：

  10.1111/j.2042-7158.1993.tb07099.x

文献信息

• [EN] THYROID HORMONE RECEPTOR AGONISTS<br/>[FR] AGONISTES DU RÉCEPTEUR DES HORMONES THYROÏDIENNES
  申请人：INVENTISBIO SHANGHAI LTD

  公开号：WO2020073974A1

  公开（公告）日：2020-04-16

  Provided herein are novel thyroid hormone receptor (TR) agonists, e. g., having Formula I, II, or III. Also provided are methods of preparing the novel TR agonists and method of using the novel TR agonists for treating diseases or disorder modulated by TR agonists, such as NAFLD, NASH, diabetes, hyperlipidemia and/or hypercholesterolemia.

  本文提供了新型甲状腺激素受体（TR）激动剂，例如具有公式I、II或III的激动剂。还提供了制备新型TR激动剂的方法以及利用新型TR激动剂治疗由TR激动剂调节的疾病或紊乱的方法，例如NAFLD、NASH、糖尿病、高脂血症和/或高胆固醇血症。
• Use of 4' of 5'-hydroxy and 4'- or 5'-alkoxy-substituted electron transfer agents in compositions, elements, test kits and analytical methods
  申请人：Johnson & Johnson Clinical Diagnostics, Inc.

  公开号：EP0603953A1

  公开（公告）日：1994-06-29

  Aqueous compositions, test kits, test devices and methods can be used to detect hydrogen peroxide or peroxidase by generating a colorimetric or chemiluminescent signal in the presence of the analyte. Signal generation is enhanced by the presence of certain substituted 4-hydroxy- or 4-alkoxy-substituted phenyl or naphthyl electron transfer agents.

  水性组合物、检测试剂盒、检测设备和方法可用于检测过氧化氢或过氧化物酶，在被分析物存在的情况下产生比色或化学发光信号。某些取代的 4-羟基或 4-烷氧基取代的苯基或萘基电子转移剂的存在可增强信号的产生。
• Analytical element and immunoassay using a 4-hydroxy or 4-alkoxyarylacetamide as stabilizer
  申请人：Johnson & Johnson Clinical Diagnostics, Inc.

  公开号：EP0603954A2

  公开（公告）日：1994-06-29

  A dry analytical element can be used to sensitively and rapidly detect a wide variety of specific binding ligands in either a competitive binding or sandwich assay format. The assays are carried out using a peroxidase-labeled immunoreactant. The peroxidase label is stabilized with a 4-hydroxy or 4-alkoxyarylacetamide which is located in one or more zones of the element. Not only is the label stabilized with the stabilizer, but the assay is more sensitive.

  干式分析元件可用于以竞争性结合或夹心检测的形式灵敏、快速地检测各种特异性结合配体。检测使用过氧化物酶标记的免疫反应物。过氧化物酶标签用 4-羟基或 4-烷氧基芳基乙酰胺稳定，这种乙酰胺位于元件的一个或多个区域。使用稳定剂不仅可以稳定标签，还能提高检测灵敏度。
• Immunoassay using a 4-hydroxy or 4-alkoxyarylacetamide as stabilizer
  申请人：Johnson & Johnson Clinical Diagnostics, Inc.

  公开号：EP0603954B1

  公开（公告）日：2000-03-08
• Chemiluminescent reagent and assay using a substituted acetanilide for light generation
  申请人：JOHNSON & JOHNSON CLINICAL DIAGNOSTICS, INC.

  公开号：EP0704539B1

  公开（公告）日：2001-02-28