2-hydrazino-2-(methylamino)-1-nitroethene | 91220-92-7

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2-hydrazino-2-(methylamino)-1-nitroethene
• 英文别名: (1-Methylamino-2-nitroethenyl)hydrazine；[1-(Methylamino)-2-nitroethenyl]hydrazine；1-hydrazinyl-N-methyl-2-nitroethenamine
• CAS: 91220-92-7
• 化学式: C₃H₈N₄O₂
• 分子量: 132.122
• InChiKey: ROJVFBYTQKEHNL-UHFFFAOYSA-N

物化性质

• 熔点：
  178-179 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• 沸点：
  292.8±40.0 °C(Predicted)
• 密度：
  1.251±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3β,14β-dihydroxy-5β-androstane-17β-carboxaldehyde 、 2-hydrazino-2-(methylamino)-1-nitroethene 以 1,4-二氧六环 、 水 为溶剂， 反应 8.0h， 以58%的产率得到(E)-17β-({[1-(methylamino)-2-nitroethenyl]hydrazono}methyl)-5β-androstane-3β,14β-diol
  参考文献：
  名称：

  Synthesis and Quantitative Structure−Activity Relationships of 17β-(Hydrazonomethyl)-5β-androstane-3β,14β-diol Derivatives That Bind to Na⁺,K⁺-ATPase Receptor

  摘要：

  A series of 17 beta-(hydrazonomethyl)-5 beta-androstane-3 beta,14 beta-diol derivatives was synthesized and evaluated in the displacement of [H-3]ouabain binding from Na+,K+-ATPase. The data were explored with multiple linear regression and partial least-squares to find possible quantitatives structure-activity relationships. Good correlations were found between binding to the receptor and van der Waals volumes or molar refractivities of the 17 beta-hydrazonomethyl substituents and pK(a) values of the compounds. Equivalent results were obtained using the proton affinity (calculated using MOPAC) of the hydrazone residues instead of experimental pK(a). As basicity or related electronic factors of the substituents explain a significant portion of the observed changes in the activity, an ion-pair interaction between a carboxylate residue of the enzyme and the protonated 17 beta-hydrazonomethyl group, as postulated by Thomas, plays an important role in the interaction of the ligand to the Na+,K+-ATPase receptor.

  DOI：

  10.1021/jm950806n
• 作为产物：
  描述：

  N-甲基-1-甲硫基-2-硝基乙烯胺 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 0.33h， 以87%的产率得到2-hydrazino-2-(methylamino)-1-nitroethene
  参考文献：
  名称：

  潜在的组胺 H2 受体拮抗剂：含有“氨基等效”基团的雷尼替丁类似物

  摘要：

  合成了一些含有“氨基等效”基团的雷尼替丁类似物，并测试了它们的体外 H2 拮抗活性。

  DOI：

  10.1002/ardp.19843170604

文献信息

• Synthesis and Quantitative Structure−Activity Relationships of 17β-(Hydrazonomethyl)-5β-androstane-3β,14β-diol Derivatives That Bind to Na⁺,K⁺-ATPase Receptor
  作者：Luisa Quadri、Alberto Cerri、Patrizia Ferrari、Elena Folpini、Massimo Mabilia、Piero Melloni

  DOI：10.1021/jm950806n

  日期：1996.1.1

  A series of 17 beta-(hydrazonomethyl)-5 beta-androstane-3 beta,14 beta-diol derivatives was synthesized and evaluated in the displacement of [H-3]ouabain binding from Na+,K+-ATPase. The data were explored with multiple linear regression and partial least-squares to find possible quantitatives structure-activity relationships. Good correlations were found between binding to the receptor and van der Waals volumes or molar refractivities of the 17 beta-hydrazonomethyl substituents and pK(a) values of the compounds. Equivalent results were obtained using the proton affinity (calculated using MOPAC) of the hydrazone residues instead of experimental pK(a). As basicity or related electronic factors of the substituents explain a significant portion of the observed changes in the activity, an ion-pair interaction between a carboxylate residue of the enzyme and the protonated 17 beta-hydrazonomethyl group, as postulated by Thomas, plays an important role in the interaction of the ligand to the Na+,K+-ATPase receptor.
• Potential Histamine H2-Receptor Antagonists: Ranitidine Analogues Containing “Semicarbazono Equivalent” Groups
  作者：Giovanni Sorba、Roberta Fruttero、Rosella Calvino、Alberto Gasco、Marco Orsetti

  DOI：10.1002/ardp.19843170604

  日期：——

  Some ranitidine analogues containing “semicarbazono equivalent” groups were synthesized and tested for their H2‐antagonistic in vitro activity.

  合成了一些含有“氨基等效”基团的雷尼替丁类似物，并测试了它们的体外 H2 拮抗活性。