α-acetamido-N-benzyl-α-(1-pyrrolyl)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-(1-pyrrolyl)acetamide
• 英文别名: 2-acetamido-N-benzyl-2-(1-pyrrolyl)acetamide；2-acetamido-N-benzyl-2-pyrrol-1-ylacetamide
• 化学式: C₁₅H₁₇N₃O₂
• 分子量: 271.319
• InChiKey: XZHHUTMRWTVHMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  0.2
• 拓扑面积：
  63.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  α-acetamido-α-ethoxy-N-benzylacetamide 在 三溴化硼 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 α-acetamido-N-benzyl-α-(1-pyrrolyl)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

• Amino acid derivative anticonvulsant
  申请人：RESEARCH CORPORATION TECHNOLOGIES, INC.

  公开号：EP0400440A1

  公开（公告）日：1990-12-05

  The present invention relates to compounds exhibiting central nervous system (CNS) activity which are useful in the treatment of epilepsy and other CNS disorders. The compounds of this invention have the following general formula: and pharmaceutically acceptable salts thereof wherein R is aryl, aryl lower alkyl, heterocyclic or heterocyclic lower alkyl, wherein R is unsubstituted or is substituted with at least one electron withdrawing group or an electron donating group; R₁ is hydrogen or lower alkyl and R₁ is unsubstituted or is substituted with at least one electron withdrawing substituent or at least one electron donating substituent; R₂ and R₃ are independently each hydrogen, lower alkenyl, lower alkynyl, aryl lower alkyl, aryl, heterocycli, heterocycli lower alkyl or Z-Y, wherein R₂ and R₃ may be unsubstituted or substituted with at least one electron withdrawing group or electron donating group; Z is O, S, NR₄, PR₄ or a chemical bond; Y is hydrogen, lower alkyl, aryl, aryl lower alkyl, lower alkenyl, lower alkynyl, or halo, and Y may be unsubstituted or substituted with at least one electron donating group or electron donating group; provided that when Y is halo, Z is a chemical bond or ZY taken together is NR₄NR₅R₆, NR₄OR₅, ONR₄R₅, OPR₄R₅, PR₄OR₅, SNR₄R₅, NR₄SR₅, SPR₄R₅, PR₄SR₅, NR₄PR₅R₆ or PR₄NR₅R₆, R₄, R₅ and R₆ are independently hydrogen, lower alkyl, aryl, aryl lower alkyl, lower alkenyl, lower alkynyl, and R₄, R₅ and R₆ may be unsubstituted or substituted with an electron withdrawing group or an electron donating group and n is 1-4.

  本发明涉及可用于治疗癫痫和其他中枢神经系统疾病的具有中枢神经系统（CNS）活性的化合物。本发明的化合物具有以下通式： 及其药学上可接受的盐 其中 R 是芳基、芳基低级烷基、杂环或杂环低级烷基，其中 R 未被取代或被至少一个取电子基团或供电子基团取代； R₁ 是氢或低级烷基，且 R₁ 未被取代或被至少一个取电子取代基或至少一个供电子取代基取代； R₂和R₃各自独立地是氢、低级烯基、低级炔基、芳基低级烷基、芳基、杂环基、杂环基低级烷基或Z-Y，其中R₂和R₃可以未被取代或被至少一个取电子基团或捐电子基团取代； Z 是 O、S、NR₄、PR₄ 或化学键； Y 是氢、低级烷基、芳基、芳基低级烷基、低级烯基、低级炔基或卤素，并且 Y 可以是未取代的或被至少一个电子捐献基团或电子捐献基团取代的；但当 Y 是卤素时，Z 是化学键或 ZY 合在一起是 NR₄NR₅, NR₄OR₅, ONR₄R₅, OPR₄R₅, PR₄OR₅, SNR₄R₅, NR₄SR₅, SPR₄R₅, PR₄SR₅, NR₄PR₅R₆ 或 PR₄NR₅R₆ 、 R₄、R₅ 和 R₆ 独立地是氢、低级烷基、芳基、芳基低级烷基、低级烯基、低级炔基，并且 R₄、R₅ 和 R₆ 可以是未取代的，也可以是被取电子基团或供电子基团取代的，并且 n 为 1-4。
• 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