4-<1-(diethylphosphono)ethyl>pyridine | 121524-89-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 4-<1-(diethylphosphono)ethyl>pyridine
• 英文别名: 4-(1-diethylphosphonoethyl)pyridine；4-(1-Diethoxyphosphorylethyl)pyridine
• CAS: 121524-89-8
• 化学式: C₁₁H₁₈NO₃P
• 分子量: 243.243
• InChiKey: HQMCNLLHJKCNKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-<1-(diethylphosphono)ethyl>pyridine 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  4-(Phosphonoalkyl)- and 4-(phosphonoalkenyl)-2-piperidinecarboxylic acids: synthesis, activity at N-methyl-D-aspartic acid receptors and anticonvulsant activity

  摘要：

  A series of 4-(phosphonoalkyl)- and 4-(phosphonoalkenyl)-2-piperidinecarboxylic acids were synthesized, and their biological activity was assessed as competitive ligands for the NMDA receptor, both in vitro by using a receptor binding assay ([3H]CGS 19755 binding) and in vivo by using an NMDA seizure model in mice. The analogues were also evaluated in [3H]AMPA and [3H]kainate binding to assess their affinity for non-NMDA excitatory amino acid receptor subtypes. A number of these analogues show potent and selective NMDA antagonistic activity both in vitro and in vivo. Most notable are 4-(phosphonomethyl)-2-piperidinecarboxylic acid (1a) (CGS 19755) and the phosphonopropenyl analogue 1i, both of which show anticonvulsant activity in the 1-2 mg/kg ip range. With the aid of computer-assisted modeling, a putative bioactive conformation for AP-5 is hypothesized from the SAR data presented and a preliminary model for the antagonist-preferring state of the NMDA receptor is presented.

  DOI：

  10.1021/jm00129a025
• 作为产物：
  描述：

  4-氯甲基吡啶 在 sodium hydride 、 lithium diisopropyl amide 作用下， 反应 2.25h， 生成 4-<1-(diethylphosphono)ethyl>pyridine
  参考文献：
  名称：

  4-(Phosphonoalkyl)- and 4-(phosphonoalkenyl)-2-piperidinecarboxylic acids: synthesis, activity at N-methyl-D-aspartic acid receptors and anticonvulsant activity

  摘要：

  A series of 4-(phosphonoalkyl)- and 4-(phosphonoalkenyl)-2-piperidinecarboxylic acids were synthesized, and their biological activity was assessed as competitive ligands for the NMDA receptor, both in vitro by using a receptor binding assay ([3H]CGS 19755 binding) and in vivo by using an NMDA seizure model in mice. The analogues were also evaluated in [3H]AMPA and [3H]kainate binding to assess their affinity for non-NMDA excitatory amino acid receptor subtypes. A number of these analogues show potent and selective NMDA antagonistic activity both in vitro and in vivo. Most notable are 4-(phosphonomethyl)-2-piperidinecarboxylic acid (1a) (CGS 19755) and the phosphonopropenyl analogue 1i, both of which show anticonvulsant activity in the 1-2 mg/kg ip range. With the aid of computer-assisted modeling, a putative bioactive conformation for AP-5 is hypothesized from the SAR data presented and a preliminary model for the antagonist-preferring state of the NMDA receptor is presented.

  DOI：

  10.1021/jm00129a025

文献信息

• Certain phosphonic acids and derivatives
  申请人：CIBA-GEIGY AG

  公开号：EP0203891B1

  公开（公告）日：1991-05-15
• HUTCHISON, ALAN J.;WILLIAMS, MICHAEL;ANGST, CHRISTOFF;JESUS, REYNALDA DE;+, J. MED. CHEM., 32,(1989) N, C. 2171-2178
  作者：HUTCHISON, ALAN J.、WILLIAMS, MICHAEL、ANGST, CHRISTOFF、JESUS, REYNALDA DE、+

  DOI：——

  日期：——
• US4898854A
  申请人：——

  公开号：US4898854A

  公开（公告）日：1990-02-06
• US4906621A
  申请人：——

  公开号：US4906621A

  公开（公告）日：1990-03-06
• US5057506A
  申请人：——

  公开号：US5057506A

  公开（公告）日：1991-10-15