N-phenyl-α-trifluoromethyllactyl amide | 131131-30-1

• 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-phenyl-α-trifluoromethyllactyl amide
• 英文别名: Propanamide, 3,3,3-trifluoro-2-hydroxy-2-methyl-N-phenyl-；3,3,3-trifluoro-2-hydroxy-2-methyl-N-phenylpropanamide
• CAS: 131131-30-1
• 化学式: C₁₀H₁₀F₃NO₂
• 分子量: 233.19
• InChiKey: JHSBXNFXGVSVQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  2
• 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：
  5

反应信息

• 作为产物：
  描述：

  苯胺 、 R/S-3,3,3-trifluoro-2-hydroxy-2-methylproanoyl chloride 以 N,N-二甲基乙酰胺 为溶剂， 反应 1.5h， 生成 N-phenyl-α-trifluoromethyllactyl amide
  参考文献：
  名称：

  （R）-三氟-2-羟基-2-甲基丙酸的酸酐作为丙酮酸脱氢酶激酶的抑制剂。

  摘要：

  描述了从N-苯基-3,3开始优化一系列作为丙酮酸脱氢酶激酶（PDHK）抑制剂的（R）-3,3，3-三氟-2-羟基-2-甲基丙酸的苯胺衍生物，3-三氟-2-羟基-2-甲基丙酰胺1（IC（50）= 35 +/- 1.4 microM）。已经发现，在苯胺的邻位上的小的吸电子基团，即氯，乙酰基或溴，增加了20-40倍的效力。当苯胺在4位被吸电子基团（即羧基，羧酰胺和亚磺酰胺）取代时，该系列化合物的口服生物利用度最佳（通过AUC测定）。N-（2-氯-4-异丁基氨磺酰基苯基）-（R）-3,3,3-三氟-2-羟基-2-甲基丙酰胺（10a）在主酶分析中抑制PDHK，IC（50）为13 + /-1.5 nM，增强人成纤维细胞中[[14] C]乳酸盐氧化成（14）CO（2）的活性，口服剂量低至30 micromol / kg后2.5和5 h显着降低血液乳酸水平，并增加肌肉，肾脏，肝脏和心脏组织中的PDH。但是

  DOI：

  10.1021/jm0000923

文献信息

• Self-disproportionation of enantiomers of α-trifluoromethyl lactic acid amides via sublimation
  作者：Manabu Yasumoto、Hisanori Ueki、Vadim A. Soloshonok

  DOI：10.1016/j.jfluchem.2009.11.010

  日期：2010.4

  subjected to sublimation under kinetic conditions (Petri dish in open air), the enantiomeric excess of the remainder has noticeably increased. On the other hand, the SDE of Bn amide derivative by sublimation resulted in almost no change in the optical purity of the remainder. These preliminary results on the SDE of the compounds under study, as well as their excellent chemical and physico-chemical characteristics

  已经开发了外消旋和对映体富集的α-三氟甲基乳酸酰胺[NHPh，NH（4-Cl-C 6 H 5），NHBn，NH t -Bu ]衍生物的制备。发现Ph，4-Cl-C 6 H 5和叔-Bu衍生物通过升华具有相当大的对映体自歧化度（SDE）。例如，当光学富集的Ph，4-Cl-C 6 H 5和叔-Bu酰胺衍生物在动力学条件下（露天培养皿）升华，剩余的对映体过量显着增加。另一方面，通过升华的Bn酰胺衍生物的SDE几乎没有改变其余部分的光学纯度。对所研究化合物的SDE的这些初步结果，以及其优异的化学和物理化学特性，使得这些酰胺衍生物易于获得，并且对于通过升华进行SDE的系统研究而言，是非常有前途的底物。
• Substituted n-phenyl 2-hydroxy-2-methyl-3,3,3-trifluropropanamide derivatives which elevate pyruvate dehydrogenase activity
  申请人：Butlin John Roger

  公开号：US20050026931A1

  公开（公告）日：2005-02-03

  Compounds of formula (I) wherein R is methyl or mesyl; and pharmaceutically acceptable salts and in vivo hydrolysable esters thereof are described. Also described are processes for their preparation, pharmaceutical compositions containing it and their use in producing an elevation of PDH activity in a warm-blooded animal.

  本文描述了化学式（I）的化合物，其中R为甲基或甲磺基；以及其药学上可接受的盐和体内可水解的酯。还描述了它们的制备过程，包括含有它们的制药组合物以及它们在产生温血动物中PDH活性升高方面的用途。
• Non-steroidal antiandrogens. Design of novel compounds based on an infrared study of the dominant conformation and hydrogen-bonding properties of a series of anilide antiandrogens
  作者：Jeffrey J. Morris、Leslie R. Hughes、Alasdair T. Glen、Peter J. Taylor

  DOI：10.1021/jm00105a067

  日期：1991.1

  Antiandrogenic activity is observed in anilides containing a tertiary hydroxyl group, and these compounds are used to define a pharmacophore in terms of their physicochemical properties. Infrared spectroscopy shows that these anilides exist in a single conformation, which exerts a powerful influence on the hydrogen-bond donor ability of the hydroxyl group in a model system. Arguments are presented which suggest that hydrogen-bonding ability is an important contributor to biological activity. Compounds were synthesized that reproduced these properties in series not containing an amide bond. Such compounds were found to exhibit good antiandrogen activity. We suggest that quantitative information on hydrogen bonding might also be useful in other systems.
• MORRIS, JEFFREY J.;HUGHES, LESLIE R.;GLEN, ALASDAIR T.;TAYLOR, PETER J., J. MED. CHEM., 34,(1991) N, C. 447-455
  作者：MORRIS, JEFFREY J.、HUGHES, LESLIE R.、GLEN, ALASDAIR T.、TAYLOR, PETER J.

  DOI：——

  日期：——
• SUBSTITUTED N-PHENYL 2-HYDROXY-2-METHYL-3,3,3-TRIFLUOROPROPANAMIDE DERIVATIVES WHICH ELEVATE PYRUVATE DEHYDROGENASE ACTIVITY
  申请人：AstraZeneca AB

  公开号：EP1214296A1

  公开（公告）日：2002-06-19