(R)-N-(4'-trifluoromethoxybiphenyl-4-yl)methyl-2-acetamido-3-methoxypropionamide | 1262534-72-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-N-(4'-trifluoromethoxybiphenyl-4-yl)methyl-2-acetamido-3-methoxypropionamide
• 英文别名: (2R)-2-acetamido-3-methoxy-N-[[4-[4-(trifluoromethoxy)phenyl]phenyl]methyl]propanamide
• CAS: 1262534-72-4
• 化学式: C₂₀H₂₁F₃N₂O₄
• 分子量: 410.393
• InChiKey: JDUJPGAUZQDZEM-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  对溴苄胺 在 N-甲基吗啉 、 盐酸 、 potassium carbonate 、 三乙胺 、 sodium hydroxide 、 silver(l) oxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 1.36h， 生成 (R)-N-(4'-trifluoromethoxybiphenyl-4-yl)methyl-2-acetamido-3-methoxypropionamide
  参考文献：
  名称：

  Substituted N-(Biphenyl-4′-yl)methyl (R)-2-Acetamido-3-methoxypropionamides: Potent Anticonvulsants That Affect Frequency (Use) Dependence and Slow Inactivation of Sodium Channels

  摘要：

  We prepared 13 derivatives of N-(biphenyl-4'-yl)methyl (R)-2-acetamido-3-methoxypropionamide that differed in type and placement of a R-substituent in the terminal aryl unit. We demonstrated that the R-substituent impacted the compound's whole animal and cellular pharmacological activities. In rodents, select compounds exhibited excellent anticonvulsant activities and protective indices (PI = TD50/ED50) that compared favorably with clinical antiseizure drugs. Compounds with a polar, aprotic R-substituent potently promoted Na+ channel slow inactivation and displayed frequency (use) inhibition of Na+ currents at low micromolar concentrations. The possible advantage of affecting these two pathways to decrease neurological hyperexcitability is discussed.

  DOI：

  10.1021/jm500707r

文献信息

• Novel N-Benzylamide Substituted Derivatives of 2-(Acylamido)acetic Acid and 2-(Acylamido)propionic Acids: Potent Neurological Agents
  申请人：Kohn Harold L.

  公开号：US20120232015A1

  公开（公告）日：2012-09-13

  A first aspect of the invention is a compound (sometimes also referred to herein as an “active agent” or “active compound”) of Formula Ia, or more particularly Formula Ib, or a pharmaceutically acceptable salt or prodrug thereof. Compositions thereof and methods of using the same (e.g. for the treatment of a neurological disease) are also described.

  本发明的第一个方面是公式Ia的化合物（有时也在此处称为“活性剂”或“活性化合物”）或更具体地为公式Ib的化合物，或其药物可接受的盐或前药。还描述了其组成物和使用方法（例如，用于治疗神经系统疾病）。
• US20140342989A1
  申请人：——

  公开号：US20140342989A1

  公开（公告）日：2014-11-20
• US8829033B2
  申请人：——

  公开号：US8829033B2

  公开（公告）日：2014-09-09
• US8933065B2
  申请人：——

  公开号：US8933065B2

  公开（公告）日：2015-01-13
• [EN] NOVEL N-BENZYLAMIDE SUBSTITUTED DERIVATIVES OF 2-(ACYLAMIDO)ACETIC ACID AND 2-(ACYLAMIDO)PROPIONIC ACIDS: POTENT NEUROLOGICAL AGENTS<br/>[FR] NOUVEAUX DÉRIVÉS À SUBSTITUTION N-BENZYLAMIDE D'ACIDE 2-(ACYLAMIDO)ACÉTIQUE ET D'ACIDES 2-(ACYLAMIDO)PROPIONIQUES : AGENTS NEUROLOGIQUES PUISSANTS
  申请人：UNIV NORTH CAROLINA

  公开号：WO2011037833A2

  公开（公告）日：2011-03-31

  A first aspect of the invention is a compound (sometimes also referred to herein as an "active agent" or "active compound") of Formula Ia, or more particularly Formula Ib, or a pharmaceutically acceptable salt or prodrug thereof. Compositions thereof and methods of using the same (e.g. for the treatment of a neurological disease) are also described.