2-(2'-aminoethyl)amine-3',4',5',6'-tetrahydropyrimidine | 790655-77-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-(2'-aminoethyl)amine-3',4',5',6'-tetrahydropyrimidine
• 英文别名: N-(1,4,5,6-tetrahydro-pyrimidin-2-yl)-ethylenediamine；N-(1,4,5,6-Tetrahydro-pyrimidin-2-yl)-aethylendiamin；N'-(1,4,5,6-tetrahydropyrimidin-2-yl)ethane-1,2-diamine
• CAS: 790655-77-5
• 化学式: C₆H₁₄N₄
• mdl: MFCD19205890
• 分子量: 142.204
• InChiKey: KCJFCQAGUUUWRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  62.4
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2'-aminoethyl)amine-3',4',5',6'-tetrahydropyrimidine 、 meso-Tetra(4-carboxyphenyl)porphine 在 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙二醇二甲醚 为溶剂， 反应 48.0h， 生成 5,10,15,20-tetrakis{4-[(2'-amino-1',4',5',6'-tetrahydropyrimidine)-2-(ethylamino)carbonyl]phenyl}-21H-23H-porphine tetrahydroiodide
  参考文献：
  名称：

  Novel Cationic Transport Agents for Oligonucleotide Delivery into Primary Leukemic Cells

  摘要：

  Novel cationic compounds forming complexes with oligodeoxyribonucleotides (ODNs) were prepared, and their ability to transport ODNs into cultured primary leukemic cells was tested. Two cationic porphyrin derivatives (2 and 3) were found to be at least 1 order of magnitude more efficient in this respect than commercially available agents. The ODN transporting capacity of novel compounds was dependent on the magnitude and the nature of their positive charges as well as on the porphyrin/ODN molar ratio. Porphyrin-ODN complexes were internalized into cells, and their dissociation was demonstrated by accumulation of fluorescein isothiocyanate-ODN fluorescence in the nucleus. Importantly, porphyrin 3 significantly protected complexed ODN against degradation and efficiently mediated the specific antisense effect on targeted v-Myb expression, resulting in reproducible growth inhibition of treated cells. Low toxicity, serum compatibility, and water solubility of porphyrin 3 make this compound a promising novel tool for modulation of gene expression in primary leukemic cells.

  DOI：

  10.1021/jm021060d
• 作为产物：
  描述：

  乙二胺 、 1,4,5,6-四氢-N-硝基-2-嘧啶胺 生成 2-(2'-aminoethyl)amine-3',4',5',6'-tetrahydropyrimidine 、 N,N'-bis-(1,4,5,6-tetrahydro-pyrimidin-2-yl)-ethylenediamine
  参考文献：
  名称：

  The Reaction of Amines with 2-Nitramino-1,3-diaza-2-cycloalkenes

  摘要：

  DOI：

  10.1021/ja01163a113

文献信息

• The Reaction of Amines with 2-Nitramino-1,3-diaza-2-cycloalkenes
  作者：A. F. McKay、J. R. Coleman、Gordon A. Grant

  DOI：10.1021/ja01163a113

  日期：1950.7
• Novel Cationic Transport Agents for Oligonucleotide Delivery into Primary Leukemic Cells
  作者：Jarmila Králová、Michal Dvořák、Vladimír Král

  DOI：10.1021/jm021060d

  日期：2003.5.1

  Novel cationic compounds forming complexes with oligodeoxyribonucleotides (ODNs) were prepared, and their ability to transport ODNs into cultured primary leukemic cells was tested. Two cationic porphyrin derivatives (2 and 3) were found to be at least 1 order of magnitude more efficient in this respect than commercially available agents. The ODN transporting capacity of novel compounds was dependent on the magnitude and the nature of their positive charges as well as on the porphyrin/ODN molar ratio. Porphyrin-ODN complexes were internalized into cells, and their dissociation was demonstrated by accumulation of fluorescein isothiocyanate-ODN fluorescence in the nucleus. Importantly, porphyrin 3 significantly protected complexed ODN against degradation and efficiently mediated the specific antisense effect on targeted v-Myb expression, resulting in reproducible growth inhibition of treated cells. Low toxicity, serum compatibility, and water solubility of porphyrin 3 make this compound a promising novel tool for modulation of gene expression in primary leukemic cells.