Diethyl-2-(dimethylamino)-ethoxycarbonylmethylphosponat | 26559-63-7

• 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: Diethyl-2-(dimethylamino)-ethoxycarbonylmethylphosponat
• 英文别名: 2-(Dimethylamino)ethyl 2-diethoxyphosphorylacetate
• CAS: 26559-63-7
• 化学式: C₁₀H₂₂NO₅P
• 分子量: 267.262
• InChiKey: SRHPTWWYFJFQDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Diethyl-2-(dimethylamino)-ethoxycarbonylmethylphosponat 在 盐酸 、 sodium hydride 作用下， 以 1,4-二氧六环 为溶剂， 反应 144.83h， 生成 (E)-(S)-4-((2R,4aS,4bS,7S,8aR,10aR)-7-Hydroxy-2,4b-dimethyl-1-oxo-tetradecahydro-phenanthren-2-yl)-hex-2-enoic acid 2-dimethylamino-ethyl ester
  参考文献：
  名称：

  A New Approach to the Design of Novel Inhibitors of Na⁺,K⁺-ATPase:  17α-Substituted Seco-D 5β-Androstane as Cassaine Analogues

  摘要：

  A new three-dimensional model for the relative binding mode of cassaine 1 and digitoxigenin 2 at the digitalis receptor site is proposed on the basis of the structural and conformational similarities among 1, 2 and its 14,15-seco analogues 3 and 4. Accordingly, the speculation that also 17 alpha-substituted derivatives of the digitalis 5 beta,14 beta-androstane skeleton could efficiently bind to the Na+,K+-ATPase receptor is put forward and verified through the synthesis of some related compounds. The binding affinity shown by 2-(N,N-dimethylamino)ethyl 3 beta,14-dihydroxy-5 beta,14 beta-androstane-17 alpha-acrylate 6 (IC50 = 5.89 mu M) and, much more significantly, by the corresponding 14,15-seco-14-oxo derivative 9 (IC50 = 0.12 mu M) substantiates the new hypothesis and opens new prospects to the design of novel inhibitors of Na+,K+-ATPase as potential positive inotropic compounds.

  DOI：

  10.1021/jm980108d
• 作为产物：
  描述：

  N,N-二甲基乙醇胺 、 二乙基磷乙酸 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 144.0h， 以98%的产率得到Diethyl-2-(dimethylamino)-ethoxycarbonylmethylphosponat
  参考文献：
  名称：

  A New Approach to the Design of Novel Inhibitors of Na⁺,K⁺-ATPase:  17α-Substituted Seco-D 5β-Androstane as Cassaine Analogues

  摘要：

  A new three-dimensional model for the relative binding mode of cassaine 1 and digitoxigenin 2 at the digitalis receptor site is proposed on the basis of the structural and conformational similarities among 1, 2 and its 14,15-seco analogues 3 and 4. Accordingly, the speculation that also 17 alpha-substituted derivatives of the digitalis 5 beta,14 beta-androstane skeleton could efficiently bind to the Na+,K+-ATPase receptor is put forward and verified through the synthesis of some related compounds. The binding affinity shown by 2-(N,N-dimethylamino)ethyl 3 beta,14-dihydroxy-5 beta,14 beta-androstane-17 alpha-acrylate 6 (IC50 = 5.89 mu M) and, much more significantly, by the corresponding 14,15-seco-14-oxo derivative 9 (IC50 = 0.12 mu M) substantiates the new hypothesis and opens new prospects to the design of novel inhibitors of Na+,K+-ATPase as potential positive inotropic compounds.

  DOI：

  10.1021/jm980108d

文献信息

• GB1175219
  申请人：——

  公开号：——

  公开（公告）日：——
• A New Approach to the Design of Novel Inhibitors of Na⁺,K⁺-ATPase:  17α-Substituted Seco-D 5β-Androstane as Cassaine Analogues
  作者：Sergio De Munari、Paolo Barassi、Alberto Cerri、Giorgio Fedrizzi、Mauro Gobbini、Massimo Mabilia、Piero Melloni

  DOI：10.1021/jm980108d

  日期：1998.7.1

  A new three-dimensional model for the relative binding mode of cassaine 1 and digitoxigenin 2 at the digitalis receptor site is proposed on the basis of the structural and conformational similarities among 1, 2 and its 14,15-seco analogues 3 and 4. Accordingly, the speculation that also 17 alpha-substituted derivatives of the digitalis 5 beta,14 beta-androstane skeleton could efficiently bind to the Na+,K+-ATPase receptor is put forward and verified through the synthesis of some related compounds. The binding affinity shown by 2-(N,N-dimethylamino)ethyl 3 beta,14-dihydroxy-5 beta,14 beta-androstane-17 alpha-acrylate 6 (IC50 = 5.89 mu M) and, much more significantly, by the corresponding 14,15-seco-14-oxo derivative 9 (IC50 = 0.12 mu M) substantiates the new hypothesis and opens new prospects to the design of novel inhibitors of Na+,K+-ATPase as potential positive inotropic compounds.