N,N-bis[2-(2-pyridyl)ethyl]-2-(4-nitrophenyl)ethylamine

• 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[2-(2-pyridyl)ethyl]-2-(4-nitrophenyl)ethylamine
• 英文别名: N,N-bis[2-(2-pyridyl)ethyl]-2-(p-nitrophenyl)ethylamine；2-(4-nitrophenyl)-N,N-bis(2-pyridin-2-ylethyl)ethanamine
• 化学式: C₂₂H₂₄N₄O₂
• 分子量: 376.458
• InChiKey: SQGIPANQLFHSRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-bis[2-(2-pyridyl)ethyl]-2-(4-nitrophenyl)ethylamine 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以92.1%的产率得到
  参考文献：
  名称：

  Site-specific DNA oxidation by a dinuclear copper complex containing a photoisomerizable azobenzene ligand

  摘要：

  A dinuclear copper complex possessing an azobenzene backbone (Cu-2(II) 1) was synthesized and its affinity towards DNA was investigated and found to be dependent on the trans-cis isomeric forms. Upon exposure to UV light at 365 nm the trans form of the complex (Cu-2(II) trans-1) underwent photoisomerization into the cis-isomer (Cu-2(II) cis-1), which reverted to the original trans-form on exposure to visible light at 420 nm. Both the trans and cis isomers exhibited moderate DNA cleavage activity toward plasmid duplex DNA in the presence of a reducing agent 3-mercaptopropionic acid (MPA) suggesting that the CuI species could activate molecular oxygen to form a reactive oxygen species in situ. Interestingly, the isomeric copper complexes showed different site-specificities in the oxidation of an oligodeoxynucleotide having single-strand-double-helix junctions in the sequence. The trans isomer Cu-2(I) trans-1 induced oxidation at the consecutive deoxyguanosine site (GG) near the junction; on the other hand, such sitespecificity was not observed in the case of Cu-2(I) cis-1. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.06.037
• 作为产物：
  描述：

  2-乙烯基吡啶 、 4-硝基苯乙胺盐酸盐 在 sodium hydroxide 、 溶剂黄146 作用下， 以 水 、 甲醇 为溶剂， 反应 8.0h， 以50.8%的产率得到N,N-bis[2-(2-pyridyl)ethyl]-2-(4-nitrophenyl)ethylamine
  参考文献：
  名称：

  Site-specific DNA oxidation by a dinuclear copper complex containing a photoisomerizable azobenzene ligand

  摘要：

  A dinuclear copper complex possessing an azobenzene backbone (Cu-2(II) 1) was synthesized and its affinity towards DNA was investigated and found to be dependent on the trans-cis isomeric forms. Upon exposure to UV light at 365 nm the trans form of the complex (Cu-2(II) trans-1) underwent photoisomerization into the cis-isomer (Cu-2(II) cis-1), which reverted to the original trans-form on exposure to visible light at 420 nm. Both the trans and cis isomers exhibited moderate DNA cleavage activity toward plasmid duplex DNA in the presence of a reducing agent 3-mercaptopropionic acid (MPA) suggesting that the CuI species could activate molecular oxygen to form a reactive oxygen species in situ. Interestingly, the isomeric copper complexes showed different site-specificities in the oxidation of an oligodeoxynucleotide having single-strand-double-helix junctions in the sequence. The trans isomer Cu-2(I) trans-1 induced oxidation at the consecutive deoxyguanosine site (GG) near the junction; on the other hand, such sitespecificity was not observed in the case of Cu-2(I) cis-1. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.06.037

文献信息

• Mechanistic Studies of Aliphatic Ligand Hydroxylation of a Copper Complex by Dioxygen:  A Model Reaction for Copper Monooxygenases
  作者：Shinobu Itoh、Hajime Nakao、Lisa M. Berreau、Toshihiko Kondo、Mitsuo Komatsu、Shunichi Fukuzumi

  DOI：10.1021/ja972809q

  日期：1998.4.1

  studies on the aliphatic ligand hydroxylation in a copper complex of tridentate ligand 1a N,N-bis[2-(2-pyridyl)ethyl]-2-phenylethylamine} by O2 have been performed in order to shed light on the structure and reactivity of the active oxygen species of our functional model for copper monooxygenases (Itoh, S.; et al. J. Am. Chem. Soc. 1995, 117, 4714). When the copper complex [CuII(1a)(ClO4)2] was treated

  已经对三齿配体 1a N,N-双[2-(2-吡啶基)乙基]-2-苯乙胺}的铜络合物中脂肪族配体羟基化的机理进行了研究，以阐明 O2 的结构和我们的铜单加氧酶功能模型的活性氧物种的反应性（Itoh, S.；等人，J. Am. Chem. Soc. 1995, 117, 4714）。当铜配合物 [CuII(1a)(ClO4)2] 在 CH2Cl2 中在 O2 气氛下用等摩尔量的安息香和三乙胺处理时，在配体的苄基位置选择性地发生有效的羟基化，以提供氧化产物 2a N,N -双[2-(2-吡啶基)乙基]-2-苯基-2-羟基乙胺}。使用 18O2 的同位素标记实验证实，2a 中 OH 基团的氧原子来自分子氧。使用 UV-vis 的光谱分析，
• Site-specific DNA oxidation by a dinuclear copper complex containing a photoisomerizable azobenzene ligand
  作者：Takeo Ito、Kanako Akamatsu、Kouhei Takeuchi、Manami Satani、Kazuhito Tanabe、Sei-ichi Nishimoto

  DOI：10.1016/j.ica.2013.06.037

  日期：2013.11

  A dinuclear copper complex possessing an azobenzene backbone (Cu-2(II) 1) was synthesized and its affinity towards DNA was investigated and found to be dependent on the trans-cis isomeric forms. Upon exposure to UV light at 365 nm the trans form of the complex (Cu-2(II) trans-1) underwent photoisomerization into the cis-isomer (Cu-2(II) cis-1), which reverted to the original trans-form on exposure to visible light at 420 nm. Both the trans and cis isomers exhibited moderate DNA cleavage activity toward plasmid duplex DNA in the presence of a reducing agent 3-mercaptopropionic acid (MPA) suggesting that the CuI species could activate molecular oxygen to form a reactive oxygen species in situ. Interestingly, the isomeric copper complexes showed different site-specificities in the oxidation of an oligodeoxynucleotide having single-strand-double-helix junctions in the sequence. The trans isomer Cu-2(I) trans-1 induced oxidation at the consecutive deoxyguanosine site (GG) near the junction; on the other hand, such sitespecificity was not observed in the case of Cu-2(I) cis-1. (C) 2013 Elsevier B.V. All rights reserved.