cis-1-(benzoylamino)-3-<2-(dimethoxyphosphoryl)-ethenyl>cyclobutane-1-N,N-pentamethylenecarboxamide | 161181-70-0

• 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: cis-1-(benzoylamino)-3-<2-(dimethoxyphosphoryl)-ethenyl>cyclobutane-1-N,N-pentamethylenecarboxamide
• CAS: 161181-70-0
• 化学式: C₂₁H₂₉N₂O₅P
• 分子量: 420.445
• InChiKey: VTLQYCHEABGJKF-PNYOVJAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  84.94
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  cis-1-(benzoylamino)-3-<2-(dimethoxyphosphoryl)-ethenyl>cyclobutane-1-N,N-pentamethylenecarboxamide 在 Adam’s catalyst 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以160 mg的产率得到cis-1-(benzoylamino)-3-<2-(dimethoxyphosphoryl)-ethyl>cyclobutane-1-N,N-pentamethylenecarboxamide
  参考文献：
  名称：

  Synthesis, NMDA Receptor Antagonist Activity, and Anticonvulsant Action of 1-Aminocyclobutanecarboxylic Acid Derivatives

  摘要：

  A range of cis- and trans-3-substituted 1-aminocyclobutane-1-carboxylic acids has been synthesized and evaluated for antagonism at excitatory amino acid receptor sites and for anticonvulsant activity. Potent and selective antagonist:activity at N-methyl-D-aspartate (NMDA) receptor sites in neonatal rat motoneurones was shown by compounds in which the 3-substituent was, or contained, a 2'-carboxyethyl or 2'-phosphonoethyl moiety. Substances 4b, 24, 35, and 40 were more potent than the standard NMDA receptor antagonist, D-2-amino-5-phosphonopentanoate (D-AP5) as NMDA antagonists in this preparation, and about equipotent with [3-(+/-)-2-carboxypiperazin-4-yl)-1-propyl]phosphonate (CPP). Anticonvulsant activity, as assessed following intracerebroventricular injection into audiogenic DBA/2 mice, generally paralleled NMDA receptor antagonist activity.

  DOI：

  10.1021/jm00051a005
• 作为产物：
  描述：

  cis-1-(benzoylamino)-3-<2-(dimethoxyphosphoryl)-1-<(methylsulfonyl)oxy>ethyl>cyclobutane-1-N,N-pentamethylenecarboxamide 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以93%的产率得到cis-1-(benzoylamino)-3-<2-(dimethoxyphosphoryl)-ethenyl>cyclobutane-1-N,N-pentamethylenecarboxamide
  参考文献：
  名称：

  Synthesis, NMDA Receptor Antagonist Activity, and Anticonvulsant Action of 1-Aminocyclobutanecarboxylic Acid Derivatives

  摘要：

  A range of cis- and trans-3-substituted 1-aminocyclobutane-1-carboxylic acids has been synthesized and evaluated for antagonism at excitatory amino acid receptor sites and for anticonvulsant activity. Potent and selective antagonist:activity at N-methyl-D-aspartate (NMDA) receptor sites in neonatal rat motoneurones was shown by compounds in which the 3-substituent was, or contained, a 2'-carboxyethyl or 2'-phosphonoethyl moiety. Substances 4b, 24, 35, and 40 were more potent than the standard NMDA receptor antagonist, D-2-amino-5-phosphonopentanoate (D-AP5) as NMDA antagonists in this preparation, and about equipotent with [3-(+/-)-2-carboxypiperazin-4-yl)-1-propyl]phosphonate (CPP). Anticonvulsant activity, as assessed following intracerebroventricular injection into audiogenic DBA/2 mice, generally paralleled NMDA receptor antagonist activity.

  DOI：

  10.1021/jm00051a005