3-(benzoylamino)-3-(pentamethylenecarbamoyl)-1-(phenylsulfonyl)cyclobutane-1-carboxylic acid | 161181-44-8

• 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: 3-(benzoylamino)-3-(pentamethylenecarbamoyl)-1-(phenylsulfonyl)cyclobutane-1-carboxylic acid
• 英文别名: 3-Benzamido-1-(benzenesulfonyl)-3-(piperidine-1-carbonyl)cyclobutane-1-carboxylic acid
• CAS: 161181-44-8
• 化学式: C₂₄H₂₆N₂O₆S
• 分子量: 470.546
• InChiKey: ZPQSRYIQFPRQGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(benzoylamino)-3-(pentamethylenecarbamoyl)-1-(phenylsulfonyl)cyclobutane-1-carboxylic acid 在 盐酸 、 sodium amalgam 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 27.0h， 生成 1-AMINOCYCLOBUTANE-CIS-1,3-DICARBOXYLIC 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-N,N-pentamethylene-3-(phenylsulfonyl)cyclobutane-1-carboxamide 在 palladium on activated charcoal 正丁基锂 、 氢气 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， -50.0~20.0 ℃ 、101.33 kPa 条件下， 反应 22.0h， 生成 3-(benzoylamino)-3-(pentamethylenecarbamoyl)-1-(phenylsulfonyl)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

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.