N,N'-bis<3-(tosylamino)propyl>-N,N'-ditosyl-1,4-butanediamine | 113812-13-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N'-bis<3-(tosylamino)propyl>-N,N'-ditosyl-1,4-butanediamine
• 英文别名: 1,5,10,14-tetratosyl-1,5,10,14-tetraazatetradecane；N¹,N⁴,N⁹,N¹²-tetratosylspermine；N¹,N⁴,N⁹,N¹²-tetra(p-toluenesulfonyl)-4,9-diaza-1,12-diaminododecane；4-methyl-N-[3-[(4-methylphenyl)sulfonyl-[4-[(4-methylphenyl)sulfonyl-[3-[(4-methylphenyl)sulfonylamino]propyl]amino]butyl]amino]propyl]benzenesulfonamide
• CAS: 113812-13-8
• 化学式: C₃₈H₅₀N₄O₈S₄
• 分子量: 819.101
• InChiKey: AXHJIJIULYDDDR-UHFFFAOYSA-N

物化性质

• 沸点：
  925.5±75.0 °C(predicted)
• 密度：
  1.288±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  54
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  201
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N,N'-bis<3-(tosylamino)propyl>-N,N'-ditosyl-1,4-butanediamine 在 氨 、 sodium 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 paraffin 为溶剂， 反应 17.0h， 生成 N(1),N(12)-二乙基精胺
  参考文献：
  名称：

  Synthetic polyamine analogs as antineoplastics

  摘要：

  In this paper, we report on the synthesis and biological activity of a number of N-alkylated spermine compounds. The dialkylspermines N1,N12-dimethylspermine (DMSPM-2), N1,N12-diethylspermine (DESPM-3), and N1,N12-dipropylspermine (DPSPM-4) are all shown to inhibit the growth of L1210 cells in culture with IC50 values of less than 1 microM at 96 h. Furthermore, DESPM-3 is shown to be similarly active against Daudi and HL-60 cells in culture. A structure-activity relationship is shown to exist between the position at which spermine is alkylated and its antiproliferative properties. The activity of 10 microM DESPM-3 against L1210 cells was shown to be cytostatic, with greater than 90% cell viability by trypan blue exclusion, even after a 144-h exposure. When L1210 cells were treated with 10 microM DESPM-3 over a 144-h period, their size and mitochondrial DNA content were gradually but substantially diminished. However, flow cytometric measurements of the nuclear DNA content of these treated cells at 96 h indicated only slightly reduced S and G2 populations and significant changes only after 144 h. A cloning assay performed on the cells after 96 h of exposure to this drug (10 microM) indicated that the cells were not growing. Finally, when male DBA/2 mice, inoculated with L1210 leukemia cells, were treated with DESPM-3, their life span was increased in excess of 200% relative to untreated controls. Moreover, many long-term survivors were apparently tumor free at the end of the experiment (60 days).

  DOI：

  10.1021/jm00401a019
• 作为产物：
  描述：

  N,N'-bis(3-formamidopropyl)-N,N'-ditosyl-1,4-butanediamine 在 吡啶 、 盐酸 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 N,N'-bis<3-(tosylamino)propyl>-N,N'-ditosyl-1,4-butanediamine
  参考文献：
  名称：

  天然亚甲基阵列组成的大单环多胺的设计与合成

  摘要：

  开发了一种适用于无环和环状多胺的通用合成方法。该方法以 12 种大单环多胺 1 ([17]N4) 到 12 ([35]N8) 的系统合成为例，由四种天然多胺片段、亚精胺、精胺、thermine 和热精胺的组合组成。这十二个设计的大环是由三个任意选择的关于亚甲基链阵列和氮含量（四到八个）标准定义的可能结构的用尽数量。分析了结构特征的共同元素，发现它们被还原为易于获得的三类简单的 N,N'-二甲苯基链烷二胺，它们源自二胺和三胺。通过 N 的反应系统地增加了氮含量，

  DOI：

  10.1246/bcsj.62.198

文献信息

• Influence of the chain length and metal : ligand ratio on the self-organization processes of Cu²⁺ complexes of [1 + 1] 1<i>H</i>-pyrazole azamacrocycles
  作者：Alberto Lopera、Ariadna Gil-Martínez、Javier Pitarch-Jarque、Begoña Verdejo、Salvador Blasco、M. Paz Clares、Hermas R. Jiménez、Enrique García-España

  DOI：10.1039/d0dt01056a

  日期：——

  amines 1,4,7,10-tetraazadecane (L1), 1,4,8,11-tetraazaundecane (L2) and 1,5,10,14-tetraazatetradecane (L3) are described. Potentiometric studies and HR-ESI-Mass spectrometry show the formation of dimeric binuclear Cu2+ complexes whose organization depends on the type of hydrocarbon chains connecting the amine groups. Furthermore, trinuclear or/and tetranuclear complexes are formed depending also on the

  1 H -3,5-双（氯甲基）吡唑与甲苯磺酸胺1,4,7,10-四氮杂can （L1），1,4,8,11-的反应形成三个新的[1 +1]大环描述了四氮杂十一烷（L2）和1,5,10,14-四氮杂十八烷（L3）。电位测量研究和HR-ESI-质谱研究表明，二聚双核Cu 2+络合物的形成取决于其连接胺基的烃链类型。此外，还取决于聚酰胺桥的长度和烃链的序列形成三核或/和四核配合物。[2 + 2] [Cu 2（H（H -1 L2））的晶体结构2 ]（ClO 4） 4 ·4H 2 O（ 1）和[Cu 2（H -1 L2） 2 ]（ClO 4） 2（ 2）络合物在它们两个中均显示出两个大环，它们通过金属离子自组装，将它们的吡唑酸酯片段相互连接，使其表现为双（单齿）配体。在1中，每个大环的一个中心胺与变形的方形金字塔的轴向位置结合，而其他大环保持质子化，而在2中，所有胺基均参与配位，从而产生严重变形的八面体几何形状。顺磁性11
• Bis-Heteronucleophilic Michael Addition to Divinyl Sulfone: A New Efficient Access to Macrocycles
  作者：Marie-Laure Teyssot、Martine Fayolle、Christian Philouze、Claude Dupuy

  DOI：10.1002/1099-0690(200301)2003:1<54::aid-ejoc54>3.0.co;2-r

  日期：2003.1

  The Michael addition of bis(nitrogen or sulfur) nucleophiles to divinyl sulfone provides the corresponding macrocyclic adducts in good yields. The structures of some new macrocyclic sulfones are established by X-ray crystallographic analysis and NMR spectroscopy. The subsequent cleavage of benzyl or tosyl groups yields the unprotected macrocyclic sulfones.
• T7 RNA polymerase activation and improvement of the transcriptional sequencing by polyamines
  作者：Masaaki Iwata、Masaki Izawa、Nobuya Sasaki、Yoko Nagumo、Hiroyuki Sasabe、Yoshihide Hayashizaki

  DOI：10.1016/s0968-0896(00)00156-5

  日期：2000.8

  We examined the possibility to improve the effectiveness of the in vitro transcription system using T7 RNA polymerase by coexistence with organic bases. The effect of the additives was evaluated by measuring the amount of RNA products in comparison with that of the control system (without additive). We found that four commercial bases and a series of ethylated polyamine analogues newly designed were active enhancers in the following activation order, 1,8-bis(ethylamino)octane > 1,8-octanediamine > 1,5-bis(ethylamino)-pentane > cadaverine > 1,8-bis(ethylamino)-5,14-diazaoctadecane > spermidine 1,18-bis(ethylamino)-5,14-diazaoctadecane > agmatine. It was shown that RNA products were corresponding, only in the presence of active enhancers, to the Full length size of the template DNA, and that sequencing signals were enhanced by the presence of active enhancers with high fidelity so that the transcriptional sequencing was further refined to be a highly sensitive sequencing method from a small amount of linear dsDNA, These results suggest that T7 RNA polymerase was activated by the specific binding of the polyamine additive to produce RNA transcripts with fidelity to the template DNA. Therefore, it is expected that the transcriptional sequencing in the presence of active enhancers might be a powerful and sensitive method, in place of the prevalent DNA amplification method, for genomic science projects and clinical and practical gene diagnoses. (C) 2000 Elsevier Science Ltd. Ail rights reserved.
• Burguete, M. Isabel; Diaz, Pilar; Garcia-Espana, Enrique, Chemical Communications, 1999, # 7, p. 649 - 650
  作者：Burguete, M. Isabel、Diaz, Pilar、Garcia-Espana, Enrique、Luis, Santiago V.、Miravet, Juan F.、Querol, Manuel、Ramirez

  DOI：——

  日期：——
• Thermal Removal of Boc-Protecting Groups During Preparation of Open-Chain Polyamines
  作者：Krzysztof E. Krakowiak、Jerald S. Bradshaw

  DOI：10.1080/00397919608003822

  日期：1996.11

  Per-N-tosylated 3,8-diaza-1,10-decanediamine (9), 4,9-diaza-1,12-dodecanediamine (spermine) (10) and 3,6,9,14,17,20-hexaaza-1,22-docosanediamine (11) were prepared by treating mono-BOG-protected, per-N-tosylated 1,2-ethanediamine (5), 1,3-propanediamine (6) and triethylenetetraamine (7), respectively, with 1,4-dibromobutane and removing the BOG-protecting groups at 100-120 degrees C.