ethyl 2-(4-chlorophenyl)-3-nitropropyl(diethoxymethyl)phosphinate | 125742-29-2

• 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: ethyl 2-(4-chlorophenyl)-3-nitropropyl(diethoxymethyl)phosphinate
• 英文别名: 1-chloro-4-[1-[diethoxymethyl(ethoxy)phosphoryl]-3-nitropropan-2-yl]benzene
• CAS: 125742-29-2
• 化学式: C₁₆H₂₅ClNO₆P
• 分子量: 393.804
• InChiKey: UPAXRJCHVKVFPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-chlorophenyl)-3-nitropropyl(diethoxymethyl)phosphinate 在 镍 lithium hydroxide 、 氨 、 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、100.0 kPa 条件下， 反应 3.0h， 生成 3-amino-2-(4-chlorophenyl)-propyl(diethoxymethyl)phosphinic acid
  参考文献：
  名称：

  Phosphinic Acid Analogs of GABA. 2. Selective, Orally Active GABAB Antagonists

  摘要：

  In 1987, 25 years after the synthesis of the potent and selective GABA(B) agonist baclofen (1), Kerr et al.(5) described the first GABA(B) antagonist phaclofen 2. However, phaclofen and structurally similar derivatives 3-5 did not cross the blood-brain barrier and hence were inactive in vivo as central nervous system agents. As a consequence, the therapeutic potential of GABA(B) antagonists remained unclear. In exploring GABA and baclofen derivatives by replacing the carboxylic acid residue with various phosphinic acid groups, we discovered more potent and water soluble GABA(B) antagonists. Electrophysiological experiments in vivo demonstrated that some of the new compounds were capable of penetrating the blood-brain barrier after oral administration. Neurotransmitter release experiments showed that they interacted with several presynaptic GABA(B) receptor subtypes, enhancing the release of GABA, glutamate, aspartate, and somatostatin. The new GABA(B) antagonists interacted also with postsynaptic GABA(B) receptors, as they blocked late inhibitory postsynaptic potentials. They facilitated the induction of long-term potentiation in vitro and in, vivo, suggesting potential cognition enhancing effects. Fifteen compounds were investigated in Various memory and learning paradigms in rodents. Although several compounds were found to be active, only 10 reversed the age-related deficits of old rats in a multiple-trial one-way active avoidance test after chronic treatment. The cognition facilitating effects of 10 were confirmed in learning experiments in Rhesus monkeys. The novel GABA(B) antagonists showed also protective effects in various animal models of absence epilepsy.

  DOI：

  10.1021/jm00017a016
• 作为产物：
  描述：

  原甲酸三乙酯 在 lithium diisopropyl amide 作用下， 反应 2.0h， 生成 ethyl 2-(4-chlorophenyl)-3-nitropropyl(diethoxymethyl)phosphinate
  参考文献：
  名称：

  Diethoxymethylphosphonites and phosphinates. Intermediates for thesynthesis of α,β- and X aminoalkylphosphonous acids

  摘要：

  DOI：

  10.1016/s0040-4020(01)89240-1

文献信息

• Substituted propane-phosphonous acid compounds
  申请人：Ciba-Geigy Corporation

  公开号：US04656298A1

  公开（公告）日：1987-04-07

  The compounds of the formula ##STR1## in which one of the groups R.sup.1, R.sup.2 and R.sup.3 represents hydrogen, C.sub.1-8 -alkyl, C.sub.3-6 -cycloalkyl, phenyl optionally substituted by halogeno, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy and/or trifluoromethyl, or C.sub.7-10 -phenylalkyl optionally substituted in the phenyl moiety by halogeno, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy and/or trifluormethyl, and the other two are hydrogen, or salts thereof. These compounds have valuable pharmaceutical properties.

  公式##STR1##中的化合物，其中R.sup.1、R.sup.2和R.sup.3中的一个代表氢、C.sub.1-8-烷基、C.sub.3-6-环烷基、苯基（可选择地被卤素取代）、C.sub.1-4-烷基、C.sub.1-4-烷氧基和/或三氟甲基，或C.sub.7-10-苯基烷基，苯基部分可选择地被卤素、C.sub.1-4-烷基、C.sub.1-4-烷氧基和/或三氟甲基取代，另外两个是氢，或其盐。这些化合物具有宝贵的药用性能。
• Substituted propane-phosponous acid compounds
  申请人：Ciba-Geigy Corporation

  公开号：US05457095A1

  公开（公告）日：1995-10-10

  The compounds of the formula ##STR1## in which one of the groups R.sup.1, R.sup.2 and R.sup.3 represents hydrogen, C.sub.1-8 -alkyl, C.sub.3-6 -cycloalkyl, phenyl optionally substituted by halogeno, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy and/or trifluoromethyl, or C.sub.7-10 -phenylalkyl optionally substituted in the phenyl moiety by halogeno, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy and/or trifluormethyl, and the other two are hydrogen, or salts thereof. These compounds have valuable pharmaceutical properties.

  式子为 ##STR1## 的化合物，其中R.sup.1、R.sup.2和R.sup.3中的一个代表氢、C.sub.1-8-烷基、C.sub.3-6-环烷基、苯基，该苯基可选择地被卤素、C.sub.1-4-烷基、C.sub.1-4-烷氧基和/或三氟甲基取代，或C.sub.7-10-苯基烷基，该苯基烷基可选择地被卤素、C.sub.1-4-烷基、C.sub.1-4-烷氧基和/或三氟甲基取代，另外两个为氢，或其盐。这些化合物具有有价值的药物性质。
• Substituted propane-phosphonuous acid compounds
  申请人：Ciba-Geigy Corporation

  公开号：US04772738A1

  公开（公告）日：1988-09-20

  The compounds of the formula ##STR1## in which one of the groups R.sup.1, R.sup.2 and R.sup.3 represents hydrogen, C.sub.1-8 -alkyl, C.sub.3-6 -cycloalkyl, phenyl optionally substituted by halogeno, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy and/or trifluoromethyl, or C.sub.7-10 -phenylalkyl optionally substituted in the phenyl moiety by halogeno, C.sub.1-4 -alkyl, C.sub.1-4 -alkoxy and/or trifluormethyl, and the other two are hydrogen, or salts thereof. These compounds have valuable pharmaceutical properties.

  式子为##STR1##的化合物，其中R.sup.1、R.sup.2和R.sup.3中的一个代表氢，C.sub.1-8-烷基，C.sub.3-6-环烷基，苯基，该苯基可选用卤代基，C.sub.1-4-烷基，C.sub.1-4-烷氧基和/或三氟甲基，或C.sub.7-10-苯基烷基，该苯基烷基中的苯基可选用卤代基，C.sub.1-4-烷基，C.sub.1-4-烷氧基和/或三氟甲基，而另外两个是氢，或其盐。这些化合物具有有价值的药物特性。
• Dingwall, J. G.; Ehrenfreund, J.; Hall, R. G., Phosphorus and Sulfur and the Related Elements, 1987, vol. 30, p. 571 - 574
  作者：Dingwall, J. G.、Ehrenfreund, J.、Hall, R. G.、Jack, J.

  DOI：——

  日期：——
• DINGWALL, J. G.;EHRENFREUND, J.;HALL, R. G., TETRAHEDRON, 45,(1989) N2, C. 3787-3808
  作者：DINGWALL, J. G.、EHRENFREUND, J.、HALL, R. G.

  DOI：——

  日期：——