N¹,N⁴-bis(p-nitrophenylsulfonyl)-1,4-diaminobutane | 609797-23-1

• 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: N¹,N⁴-bis(p-nitrophenylsulfonyl)-1,4-diaminobutane
• 英文别名: N,N'-di-(4-nitrobenzenesulfonyl)-1,4-diaminobutane；1,4-bis-(4-nitro-benzenesulfonylamino)-butane；1,4-Bis-(4-nitro-benzolsulfonylamino)-butan；4-nitro-N-[4-[(4-nitrophenyl)sulfonylamino]butyl]benzenesulfonamide
• CAS: 609797-23-1
• 化学式: C₁₆H₁₈N₄O₈S₂
• 分子量: 458.473
• InChiKey: GAXBYHJEDWVCPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  201
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-phthalimido-2-methylidene-3-chloropropane 、 N¹,N⁴-bis(p-nitrophenylsulfonyl)-1,4-diaminobutane 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成
  参考文献：
  名称：

  Synthesis of 2,11-bis(methylidene)spermine, a new inhibitor of spermine oxidase

  摘要：

  Earlier unknown 1,12-diamino-2,11-bis(methylidene)-4,9-diazadodecane, which may be considered as an enzyme-activated inhibitor of spermine oxidase, was synthesized in 6 steps starting from 2-chloromethyl-3-chloropropene-1 in a high yield. Application of newly synthesized spermine analogue for the inhibition of spermine oxidase was discussed.

  DOI：

  10.1134/s1068162016030080
• 作为产物：
  描述：

  四亚甲基二胺 、 对硝基苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到N¹,N⁴-bis(p-nitrophenylsulfonyl)-1,4-diaminobutane
  参考文献：
  名称：

  Synthesis of Hsp90 inhibitor dimers as potential antitumor agents

  摘要：

  Structure-based drug design was used to systematically synthesize PU3-dimers. The cytotoxicity of PU3 dimers 6 against breast cancer cell lines was evaluated, and their potency increased as the length of the bridging linker increased. Among the compounds tested, 6e with a C-20 linker was the most potent and exhibited a 20- to 30-fold increase in activity compared with that of the parent compound 5. Western blot analyses of the cell lysates treated with 6c revealed that 6c resulted in the concentration-dependent degradation of the Hsp90 client protein Her2, which is consistent with other Hsp90 inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.070

文献信息

• 64. Sulphanilamide derivatives
  作者：F. S. Spring、E. P. H. Young

  DOI：10.1039/jr9440000248

  日期：——
• N¹-(Aminoalkyl)-sulfanilamides and N¹-(Acetamidoalkyl)-sulfanilamides
  作者：Lawrence H. Amundsen、Lena A. Malentacchi

  DOI：10.1021/ja01208a015

  日期：1946.4
• Synthesis of Hsp90 inhibitor dimers as potential antitumor agents
  作者：Kazuhiro Muranaka、Akiko Sano、Satoshi Ichikawa、Akira Matsuda

  DOI：10.1016/j.bmc.2008.04.070

  日期：2008.6

  Structure-based drug design was used to systematically synthesize PU3-dimers. The cytotoxicity of PU3 dimers 6 against breast cancer cell lines was evaluated, and their potency increased as the length of the bridging linker increased. Among the compounds tested, 6e with a C-20 linker was the most potent and exhibited a 20- to 30-fold increase in activity compared with that of the parent compound 5. Western blot analyses of the cell lysates treated with 6c revealed that 6c resulted in the concentration-dependent degradation of the Hsp90 client protein Her2, which is consistent with other Hsp90 inhibitors. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of 2,11-bis(methylidene)spermine, a new inhibitor of spermine oxidase
  作者：N. A. Grigorenko、M. A. Khomutov、A. R. Simonian、S. N. Kochetkov、A. R. Khomutov

  DOI：10.1134/s1068162016030080

  日期：2016.7

  Earlier unknown 1,12-diamino-2,11-bis(methylidene)-4,9-diazadodecane, which may be considered as an enzyme-activated inhibitor of spermine oxidase, was synthesized in 6 steps starting from 2-chloromethyl-3-chloropropene-1 in a high yield. Application of newly synthesized spermine analogue for the inhibition of spermine oxidase was discussed.