4,7,10,13-四氮杂十六烷二腈 | 67990-04-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 4,7,10,13-四氮杂十六烷二腈
• 英文名称: 1,10-bis(2-cyanoethyl)triethylenetetraamine
• 英文别名: 4,7,10,13-Tetraazahexadecanedinitrile；3-[2-[2-[2-(2-cyanoethylamino)ethylamino]ethylamino]ethylamino]propanenitrile
• CAS: 67990-04-9
• 化学式: C₁₂H₂₄N₆
• 分子量: 252.363
• InChiKey: LZRSZAAWHRMGRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  18
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  95.7
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,7,10,13-四氮杂十六烷二腈 在 sodium azide 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 1,10-bis<2-(1H-tetrazol-5-yl)ethyl>triethylenetetramine hydrochloride
  参考文献：
  名称：

  Ermakova, M. I.; Shikhova, I. A.; Latosh, N. I., Journal of general chemistry of the USSR, 1981, vol. 51, # 1, p. 152 - 155

  摘要：

  DOI：
• 作为产物：
  描述：

  丙烯腈 、 三乙烯四胺 生成 4,7,10,13-四氮杂十六烷二腈
  参考文献：
  名称：

  Mukherjee; Singh; Mathur, Journal of the Indian Chemical Society, 2000, vol. 77, # 7, p. 332 - 335

  摘要：

  DOI：

文献信息

• Novel isosteric charge-deficient spermine analogue—1,12-diamino-3,6,9-triazadodecane: synthesis, pK a measurement and biological activity
  作者：Janne Weisell、Mervi T. Hyvönen、Jouko Vepsäläinen、Leena Alhonen、Tuomo A. Keinänen、Alex R. Khomutov、Pasi Soininen

  DOI：10.1007/s00726-009-0409-6

  日期：2010.2

  Ionic interactions are essential for the biological functions of the polyamines spermidine and spermine in mammalian physiology. Here, we describe a simple gram scale method to prepare 1,12-diamino-3,6,9-triazadodecane (SpmTrien), an isosteric charge-deficient spermine analogue. The protonation sites of SpmTrien were determined at pH range of 2.2-11.0 using two-dimensional H-1-N-15 NMR spectroscopy, which proved to be more feasible than conventional methods. The macroscopic pK (a) values of SpmTrien (3.3, 6.3, 8.5, 9.5 and 10.3) are significantly lower than those of 1,12-diamino-4,9-diazadodecane (spermine). The effects of SpmTrien and its parent molecule, 1,8-diamino-3,6-diazaoctane (Trien), on cell growth and polyamine metabolism were investigated in DU145 prostate carcinoma cells. SpmTrien downregulated the biosynthetic enzymes ornithine decarboxylase (ODC) and S-adenosyl-l-methionine decarboxylase and decreased intracellular polyamine levels, whereas the effects of Trien alone were minor. Interestingly, both SpmTrien and Trien were able to partially overcome growth arrest induced by an ODC inhibitor, alpha-difluoromethylornithine, indicating that they are able to mimic some functions of the natural polyamines. Thus, SpmTrien is a novel tool to influence polyamine interaction sites at the molecular level and offers a new means to study the contribution of the protonation of spermine amino group(s) in the regulation of polyamine-dependent biological processes.
• ERMAKOVA M. K.; SHIXOVA I. A.; LATOSH N. I., ZH. OBSHCH. XIMII, 1981, 51, HO 1, 174-178
  作者：ERMAKOVA M. K.、 SHIXOVA I. A.、 LATOSH N. I.

  DOI：——

  日期：——
• ZAGIDULLIN, R. N., XIM. PROM-ST,(1987) N 12, 714-716
  作者：ZAGIDULLIN, R. N.

  DOI：——

  日期：——
• Ermakova, M. I.; Shikhova, I. A.; Latosh, N. I., Journal of general chemistry of the USSR, 1981, vol. 51, # 1, p. 152 - 155
  作者：Ermakova, M. I.、Shikhova, I. A.、Latosh, N. I.

  DOI：——

  日期：——
• Mukherjee; Singh; Mathur, Journal of the Indian Chemical Society, 2000, vol. 77, # 7, p. 332 - 335
  作者：Mukherjee、Singh、Mathur

  DOI：——

  日期：——