N,N'-bis(3-dimethylamino-1-phenylpropylidene)hydrazine dihydrochloride | 118720-31-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N'-bis(3-dimethylamino-1-phenylpropylidene)hydrazine dihydrochloride
• 英文别名: 3-dimethylaminopropiophenone azine dihydrochloride；3-[[3-(dimethylamino)-1-phenylpropylidene]hydrazinylidene]-N,N-dimethyl-3-phenylpropan-1-amine;hydrochloride
• CAS: 118720-31-3
• 化学式: C₂₂H₃₀N₄*2ClH
• 分子量: 423.429
• InChiKey: MKCVHPZGWNKDHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  31.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-bis(3-dimethylamino-1-phenylpropylidene)hydrazine dihydrochloride 在 phosphate buffer 、 sodium carbonate 作用下， 以 乙醚 、 水 为溶剂， 反应 167.0h， 生成 2-(3-{[3-(2-Hydroxy-ethylsulfanyl)-1-phenyl-prop-(E)-ylidene]-hydrazono}-3-phenyl-propylsulfanyl)-ethanol
  参考文献：
  名称：

  Dimmock; Erciyas; Kirkpatrick, Pharmazie, 1988, vol. 43, # 9, p. 614 - 616

  摘要：

  DOI：
• 作为产物：
  描述：

  苯乙酮 在 盐酸 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 27.5h， 生成 N,N'-bis(3-dimethylamino-1-phenylpropylidene)hydrazine dihydrochloride
  参考文献：
  名称：

  Kucukoglu, Kaan; Gul, Mustafa; Atalay, Mustafa, Arzneimittel-Forschung/Drug Research, 2011, vol. 61, # 6, p. 366 - 371

  摘要：

  DOI：

文献信息

• Cytotoxicity of Some Azines of Acetophenone Derived Mono-Mannich Bases against Jurkat Cells
  作者：Halise Inci Gul、Mustafa Gul、Jouko Vepsälainen、Ercin Erciyas、Osmo Hänninen

  DOI：10.1248/bpb.26.631

  日期：——

  Acetophenone derived mono-Mannich bases (Ig1—Ig4), 1-aryl-3-amino-1-propanone hydrochlorides, which are known to have cytotoxicity in Jurkat cells, were synthesized. Then, they were converted to corresponding azine derivatives (D1—D4), N, N′-bis(3-amino-1-aryl-propylidene)hydrazine dihydrochlorides, which are bifunctional agents. The aryl part was replaced by phenyl in Ig1, Ig2, Ig3, D1, D2, and D3, and by p-hydroxyphenyl in Ig4 and D4. The amine part was replaced by dimethylamine in Ig1, D1, Ig4 and D4, by piperidine in Ig2 and D2, and by morpholine in Ig3 and D3. The aim of this study was to investigate whether the modification in chemical structure, converting the mono-Mannich base to a corresponding azine derivative, improves the cytotoxicity. In addition, the effect of the representative compound, D3, N, N′-bis(3-morpholine-4-yl-1-phenylpropylidene)hydrazine dihydrochloride, on cellular glutathione level after 1 h exposure in phosphate buffer at 37 °C was also determined to provide information on a possible mechanism of cytotoxic action. Compounds D2—D4 are reported for the first time in this study. Except for Ig2 and D2, the cytotoxicity of mono-Mannich bases, Ig1, Ig3 and Ig4 and corresponding azine derivatives, D1, D3 and D4 were higher than the reference compound 5-FU. Azine derivatives D1 and D4 had almost equal cytotoxic potency with corresponding mono-Mannich bases Ig1 and Ig4, respectively. On the other hand, azine derivatives D2 and D3, had 1.28 and 1.90-times less cytotoxicity in Jurkat cells compared with the mono-Mannich bases, Ig2 and Ig3, respectively, from which they are derived. Azine derivative D3 dose-dependently decreased the total cellular glutathione level, suggesting that azine derivatives may exert cytotoxicity by thiol alkylation. Azine derivatives with equal or less cytotoxic potency compared to the mono-Mannich bases they are derived from seemed to be less suitable derivatives for the development of new cytotoxic compounds.

  合成了苯乙酮衍生的单曼尼希碱（Ig1-Ig4）、1-芳基-3-氨基-1-丙酮盐酸盐，已知它们对 Jurkat 细胞具有细胞毒性。然后，将它们转化为相应的氮衍生物（D1-D4）、N，N′-双（3-氨基-1-芳基-亚丙基）肼二盐酸盐，它们是双功能制剂。芳基部分在 Ig1、Ig2、Ig3、D1、D2 和 D3 中被苯基取代，在 Ig4 和 D4 中被对羟基苯基取代。胺部分在 Ig1、D1、Ig4 和 D4 中被二甲胺取代，在 Ig2 和 D2 中被哌啶取代，在 Ig3 和 D3 中被吗啉取代。本研究的目的是探讨化学结构的改变（将单曼尼希碱转化为相应的氮衍生物）是否会提高细胞毒性。此外，还测定了代表性化合物 D3（N, N′-双（3-吗啉-4-基-1-苯基亚丙基）肼二盐酸盐）在 37 °C 磷酸盐缓冲液中暴露 1 小时后对细胞谷胱甘肽水平的影响，以提供有关细胞毒性作用的可能机制的信息。本研究首次报告了 D2-D4 化合物。除 Ig2 和 D2 外，单曼尼希碱、Ig1、Ig3 和 Ig4 以及相应的偶氮衍生物 D1、D3 和 D4 的细胞毒性均高于参考化合物 5-FU。叠氮衍生物 D1 和 D4 与相应的单曼尼希碱 Ig1 和 Ig4 的细胞毒性效力几乎相同。另一方面，叠氮衍生物 D2 和 D3 在 Jurkat 细胞中的细胞毒性分别比其衍生的单曼尼希碱基 Ig2 和 Ig3 低 1.28 倍和 1.90 倍。叠氮衍生物 D3 可剂量依赖性地降低细胞谷胱甘肽的总含量，这表明叠氮衍生物可能是通过硫醇烷基化作用来产生细胞毒性的。与单曼尼希碱相比，具有相同或较低细胞毒性的叠氮衍生物似乎不太适合开发新的细胞毒性化合物。