4,4-(1E,1E)-2,2-(1,4-phenylene)-bis(ethene-2,1-diyl)bis(3-nitrobenzonitrile) | 2695-69-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4,4-(1E,1E)-2,2-(1,4-phenylene)-bis(ethene-2,1-diyl)bis(3-nitrobenzonitrile)
• 英文别名: 1,4-Bis-(4-Cyan-2-nitro-trans-styryl)-benzol；1.4-bis-(2-nitro-4-cyano-trans-styryl)-benzene；1.4-Bis-(2-nitro-4-cyan-trans-styryl)-benzol；4-[(E)-2-[4-[(E)-2-(4-cyano-2-nitrophenyl)ethenyl]phenyl]ethenyl]-3-nitrobenzonitrile
• CAS: 2695-69-4
• 化学式: C₂₄H₁₄N₄O₄
• 分子量: 422.4
• InChiKey: OMBKGCHLHBHHMG-NXZHAISVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  139
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4-(1E,1E)-2,2-(1,4-phenylene)-bis(ethene-2,1-diyl)bis(3-nitrobenzonitrile) 在 磷酸三乙酯 作用下， 反应 96.0h， 生成 1,4-bis[6-(3,4,5,6-tetrahydropyrimidin-2-yl)indol-2-yl]benzene
  参考文献：
  名称：

  Antibacterial Drug Leads: DNA and Enzyme Multitargeting

  摘要：

  We report the results of an investigation of the activity of a series of amidine and bisamidine compounds against Staphylococcus aureus and Escherichia coli. The most active compounds bound to an AT-rich DNA dodecamer (CGCGAATTCGCG)(2) and using DSC were found to increase the melting transition by up to 24 degrees C. Several compounds also inhibited undecaprenyl diphosphate synthase (UPPS) with IC50 values of 100-500 nM, and we found good correlations (R-2 = 0.89, S. aureus; R-2 = 0.79, E. coli) between experimental and predicted cell growth inhibition by using DNA Delta(Tm) and UPPS IC50 experimental results together with one computed descriptor. We also solved the structures of three bisamidines binding to DNA as well as three UPPS structures. Overall, the results are of general interest in the context of the development of resistance-resistant antibiotics that involve multitargeting.

  DOI：

  10.1021/jm501449u
• 作为产物：
  描述：

  4-甲基-3-硝基苯甲腈 、 对苯二甲醛 在 哌啶 作用下， 生成 4,4-(1E,1E)-2,2-(1,4-phenylene)-bis(ethene-2,1-diyl)bis(3-nitrobenzonitrile)
  参考文献：
  名称：

  苯甲醛和硝酸二甲苯胺的合成，以及苯甲醛和二异氰酸酯的合成（21.米特朗·杜贝尔·吲哚和Isatogene）

  摘要：

  DOI：

  10.1002/hlca.19360190103

文献信息

• Über die Kondensation der drei Phtal-aldehyde mit nitrierten Toluolen und die Darstellung von Di-isatogenen (21. Mitteilung über Indole und Isatogene)
  作者：Paul Ruggli、Eberhard Wolff

  DOI：10.1002/hlca.19360190103

  日期：——
• Colonge,J.; von Arx,P., Bulletin de la Societe Chimique de France, 1965, p. 1858 - 1862
  作者：Colonge,J.、von Arx,P.

  DOI：——

  日期：——
• Antibacterial Drug Leads: DNA and Enzyme Multitargeting
  作者：Wei Zhu、Yang Wang、Kai Li、Jian Gao、Chun-Hsiang Huang、Chun-Chi Chen、Tzu-Ping Ko、Yonghui Zhang、Rey-Ting Guo、Eric Oldfield

  DOI：10.1021/jm501449u

  日期：2015.2.12

  We report the results of an investigation of the activity of a series of amidine and bisamidine compounds against Staphylococcus aureus and Escherichia coli. The most active compounds bound to an AT-rich DNA dodecamer (CGCGAATTCGCG)(2) and using DSC were found to increase the melting transition by up to 24 degrees C. Several compounds also inhibited undecaprenyl diphosphate synthase (UPPS) with IC50 values of 100-500 nM, and we found good correlations (R-2 = 0.89, S. aureus; R-2 = 0.79, E. coli) between experimental and predicted cell growth inhibition by using DNA Delta(Tm) and UPPS IC50 experimental results together with one computed descriptor. We also solved the structures of three bisamidines binding to DNA as well as three UPPS structures. Overall, the results are of general interest in the context of the development of resistance-resistant antibiotics that involve multitargeting.