α-acetamido-N-benzyl-α-(thiazol-2-yl)acetamide

• 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: α-acetamido-N-benzyl-α-(thiazol-2-yl)acetamide
• 英文别名: 2-acetamido-N-benzyl-2-(2-thiazolyl)acetamide；2-acetamido-N-benzyl-2-(1,3-thiazol-2-yl)acetamide
• 化学式: C₁₄H₁₅N₃O₂S
• 分子量: 289.358
• InChiKey: GJSXNTZBKCDSSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  99.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  α-acetamido-N-benzyl-α-cyanoacetamide 在 二硫代磷酸二乙酯 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 16.0h， 生成 α-acetamido-N-benzyl-α-(thiazol-2-yl)acetamide
  参考文献：
  名称：

  Synthesis and anticonvulsant activities of .alpha.-heterocyclic .alpha.-acetamido-N-benzylacetamide derivatives

  摘要：

  Earlier studies showed that (R,S)-alpha-acetamido-N-benzylacetamides (2) containing a five- and six-membered aromatic or heteroaromatic group appended at the C(alpha) site displayed outstanding activity in the maximal electroshock-induced seizure (MES) test in mice. An expanded set of C(alpha)-heteroaromatic analogues of 2 have been prepared and evaluated. The observed findings extended the structure-activity relationships previously discerned for this novel class of anti-convulsants and have validated previous trends. The alpha-furan-2-yl (4), alpha-oxazol-2-yl (18), and alpha-thiazol-2-yl (19) alpha-acetamido-N-benzylacetamides afforded excellent protection against MES-induced seizures in mice. The ED50 and PI values for these adducts rivaled those reported for phenytoin. The outstanding properties provided by 4 led to an in-depth examination of the effect of structural modification at key sites within this compound on biological activity. The pharmacological data in this series indicated that stringent steric and electronic requirements existed for maximal activity and revealed the outstanding activity of (R)-(-)-alpha-acetamido-N-(4-fluorobenzyl)-alpha-(furan-2-yl)acetamide [(R)-30].

  DOI：

  10.1021/jm00074a016

文献信息

• EP0592490A4
  申请人：——

  公开号：EP0592490A4

  公开（公告）日：1994-08-17
• AMINO ACID DERIVATIVE ANTICONVULSANT
  申请人：RESEARCH CORPORATION TECHNOLOGIES, INC.

  公开号：EP0592490A1

  公开（公告）日：1994-04-20
• US5378729A
  申请人：——

  公开号：US5378729A

  公开（公告）日：1995-01-03
• US5654301A
  申请人：——

  公开号：US5654301A

  公开（公告）日：1997-08-05
• [EN] AMINO ACID DERIVATIVE ANTICONVULSANT
  申请人：RESEARCH CORPORATION TECHNOLOGIES, INC.

  公开号：WO1992021648A1

  公开（公告）日：1992-12-10

  (EN) The present invention relates to compounds of formula (I).(FR) L'invention concerne des composés ayant la formule (I).