1-Amino-3-(2-phosphono-acetyl)-cyclobutanecarboxylic acid | 161181-67-5

• 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: 1-Amino-3-(2-phosphono-acetyl)-cyclobutanecarboxylic acid
• CAS: 161181-67-5
• 化学式: C₇H₁₂NO₆P
• 分子量: 237.149
• InChiKey: SEJQDUBASDUVAS-KIRWANIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.07
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  137.92
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-Amino-3-(2-phosphono-acetyl)-cyclobutanecarboxylic acid 在 Adam’s catalyst 氢气 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 20.0h， 以175 mg的产率得到cis-1-amino-3-(2-phosphono-1-hydroxyethyl)cyclobutane-1-carboxylic acid
  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-Azido-3-(phenylsulfonyl)cyclobutane-1-carboxylic acid 在 palladium on activated charcoal 盐酸 、 sodium amalgam 、 正丁基锂 、 氯化亚砜 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 乙酸乙酯 为溶剂， -78.0~130.0 ℃ 、101.33 kPa 条件下， 反应 53.67h， 生成 1-Amino-3-(2-phosphono-acetyl)-cyclobutanecarboxylic acid
  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

文献信息

• Synthesis, NMDA Receptor Antagonist Activity, and Anticonvulsant Action of 1-Aminocyclobutanecarboxylic Acid Derivatives
  作者：Yehiel Gaoni、Astrid G. Chapman、Naila Parvez、Peter C.-K. Pook、David E. Jane、Jeffrey C. Watkins

  DOI：10.1021/jm00051a005

  日期：1994.12

  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.