ethyl 2,3-methano-4-(diethylphosphono)butanoate | 1023-78-5

• 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: ethyl 2,3-methano-4-(diethylphosphono)butanoate
• 英文别名: 2-<(Di-O-aethyl-phosphono)-methyl>-cyclopropan-carbonsaeure-(1)-aethylester；2-<(O.O-Diaethyl-phosphono)-methyl>-cyclopropan-1-carbonsaeure-aethylester；2-[(Di-O-aethyl-phosphono)-methyl]-cyclopropan-carbonsaeure-(1)-aethylester；Ethyl 2-(diethoxyphosphorylmethyl)cyclopropane-1-carboxylate；ethyl 2-(diethoxyphosphorylmethyl)cyclopropane-1-carboxylate
• CAS: 1023-78-5
• 化学式: C₁₁H₂₁O₅P
• 分子量: 264.259
• InChiKey: YBIHKBMFKSQDLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2,3-methano-4-(diethylphosphono)butanoate 在 氢氧化钾 、 硼烷四氢呋喃络合物 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 (Z)-2,3-methano-4-(diethylphosphono)butanal
  参考文献：
  名称：

  Synthesis and biological evaluation of cyclopropyl analogs of 2-amino-5-phosphonopentanoic acid

  摘要：

  A series of cyclopropyl analogues related to 2-amino-5-phosphonopentanoic acid (AP5) were synthesized and their biological activity was assessed as competitive antagonists for the N-methyl-D-aspartate (NMDA) receptor. In vitro receptor binding using [H-3]-L-glutamate as the radioligand provided affinity data, while modulation of [H-3]MK-801 binding was used as a functional assay. The analogues were also evaluated in [H-3]kainate binding to assess selectivity over non-NMDA glutamate receptors. Of the compounds tested, 4,5-methano-AP5 analogue 26 was the most potent selective NMDA antagonist; however, potency was lower than that for [[(+/-)-2-carboxypiperidin-4-yl]methyl]phosphonic acid (CGS 19755, 5).

  DOI：

  10.1021/jm00105a024

文献信息

• Synthesis and biological evaluation of cyclopropyl analogs of 2-amino-5-phosphonopentanoic acid
  作者：Michael S. Dappen、Roberto Pellicciari、Benedetto Natalini、Joseph B. Monahan、Claudio Chiorri、Alex A. Cordi

  DOI：10.1021/jm00105a024

  日期：1991.1

  A series of cyclopropyl analogues related to 2-amino-5-phosphonopentanoic acid (AP5) were synthesized and their biological activity was assessed as competitive antagonists for the N-methyl-D-aspartate (NMDA) receptor. In vitro receptor binding using [H-3]-L-glutamate as the radioligand provided affinity data, while modulation of [H-3]MK-801 binding was used as a functional assay. The analogues were also evaluated in [H-3]kainate binding to assess selectivity over non-NMDA glutamate receptors. Of the compounds tested, 4,5-methano-AP5 analogue 26 was the most potent selective NMDA antagonist; however, potency was lower than that for [[(+/-)-2-carboxypiperidin-4-yl]methyl]phosphonic acid (CGS 19755, 5).