2-[((2-(4-imidazoyl)ethyl)amino)carbonyl]-6-[((2-aminoethyl)amino)methyl]pyridine | 115171-93-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-[((2-(4-imidazoyl)ethyl)amino)carbonyl]-6-[((2-aminoethyl)amino)methyl]pyridine
• 英文别名: 2-{((2-(4-imidazolyl)ethyl)amino)carbonyl}-6-(N-(2-aminoethyl)aminomethyl)pyridine trihydrochloride；6-[(2-aminoethylamino)methyl]-N-[2-(1H-imidazol-5-yl)ethyl]pyridine-2-carboxamide
• CAS: 115171-93-2
• 化学式: C₁₄H₂₀N₆O
• 分子量: 288.352
• InChiKey: AQLQWJNRBXQAJT-UHFFFAOYSA-N

物化性质

• 沸点：
  619.2±55.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  109
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  iron(III) chloride hexahydrate 、 2-[((2-(4-imidazoyl)ethyl)amino)carbonyl]-6-[((2-aminoethyl)amino)methyl]pyridine 在 N-甲基咪唑 作用下， 以 乙醇 为溶剂， 以62%的产率得到
  参考文献：
  名称：

  Synthesis, spectroscopic, redox properties, and DNA cleavage activity of low-spin iron(III) complexes of bleomycin analogues

  摘要：

  The reaction of the bleomycin (BLM) analogues, 2-[((2-(4-imidazoyl)ethyl)amino)carbonyl]-6-[((2-aminoethyl)amino)methyl]pyridine = L-1 or 2-[((2-(4-imidazoyl)ethyl)amino)carbonyl]-6-[((2-amino-2-carbamoylethyl)amino)methyl]pyridine = L-2 with an equimolar amount of FeCl3.6H(2)O in ethanol in the presence of N-methylimidazole afforded deep-red microcrystals, [Fe-III(H- 1L1)(H2O)]Cl-2 (1) or [Fe-III(H-1L2)(H2O)]Cl-2.0.5H(2)O (2), respectively. These Fe-III complexes have been characterized by electronic and EPR spectroscopies and cyclic voltammetry. The electronic spectra of 1 and 2 in methanol are similar to that of authentic Fe-III-pepleomycin, which is a member of the family of BLMs. The EPR spectra of 1 and 2 in frozen methanol at 77 K exhibited rhombic low-spin Fe-III signals (g(1) = 2.40, g(2) = 2.32, and g(3) = 1.86 for 1 and g(1) = 2.38, g(2) = 2.31, and g(3) = 1.86 for 2). The cyclic voltammograms of 1 and 2 in DMF at I = 0.1 M tetraethylammonium chloride, TEACl, displayed one-electron Fe-III/II redox process at E-1/2 = - 0.04 V and + 0.05 V versus Ag/AgCl for 1 and 2, respectively. Both Fe-III complexes, 1 and 2, cleaved pUC19 DNA at 0.1 mM in the presence of H2O2. Complex 1 was found to cleave 293 base-pair DNA with a little selectivity as compared with the Fe-III-BLM complex, indicating that the metal-chelating moiety may be necessary for the sequence selectivity of DNA strand scission by BLM. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0020-1693(99)00279-0
• 作为产物：
  描述：

  histamine dichloride 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 2-[((2-(4-imidazoyl)ethyl)amino)carbonyl]-6-[((2-aminoethyl)amino)methyl]pyridine
  参考文献：
  名称：

  Highficld, Jackie A.; Mehta, Lina K.; Patrick, John, Journal of the Chemical Society. Perkin transactions I, 1999, # 16, p. 2343 - 2351

  摘要：

  DOI：

文献信息

• Kimura, Eiichi; Kurosaki, Hiromasa; Kurogi, Yasuhisa, Inorganic Chemistry, 1992, vol. 31, # 21, p. 4314 - 4321
  作者：Kimura, Eiichi、Kurosaki, Hiromasa、Kurogi, Yasuhisa、Shionoya, Mitsuhiko、Shiro, Motoo

  DOI：——

  日期：——
• Highficld, Jackie A.; Mehta, Lina K.; Patrick, John, Journal of the Chemical Society. Perkin transactions I, 1999, # 16, p. 2343 - 2351
  作者：Highficld, Jackie A.、Mehta, Lina K.、Patrick, John、Candeias, Luis P.、Wardman, Peter

  DOI：——

  日期：——
• Synthesis, spectroscopic, redox properties, and DNA cleavage activity of low-spin iron(III) complexes of bleomycin analogues
  作者：Hiromasa Kurosaki、Yoshinobu Ishikawa、Kentarou Hayashi、Miwako Sumi、Yoshiko Tanaka、Masafumi Goto、Kazufumi Inada、Isao Taniguchi、Mitsuhiko Shionoya、Hiroaki Matsuo、Masanori Sugiyama、Eiichi Kimura

  DOI：10.1016/s0020-1693(99)00279-0

  日期：1999.11

  The reaction of the bleomycin (BLM) analogues, 2-[((2-(4-imidazoyl)ethyl)amino)carbonyl]-6-[((2-aminoethyl)amino)methyl]pyridine = L-1 or 2-[((2-(4-imidazoyl)ethyl)amino)carbonyl]-6-[((2-amino-2-carbamoylethyl)amino)methyl]pyridine = L-2 with an equimolar amount of FeCl3.6H(2)O in ethanol in the presence of N-methylimidazole afforded deep-red microcrystals, [Fe-III(H- 1L1)(H2O)]Cl-2 (1) or [Fe-III(H-1L2)(H2O)]Cl-2.0.5H(2)O (2), respectively. These Fe-III complexes have been characterized by electronic and EPR spectroscopies and cyclic voltammetry. The electronic spectra of 1 and 2 in methanol are similar to that of authentic Fe-III-pepleomycin, which is a member of the family of BLMs. The EPR spectra of 1 and 2 in frozen methanol at 77 K exhibited rhombic low-spin Fe-III signals (g(1) = 2.40, g(2) = 2.32, and g(3) = 1.86 for 1 and g(1) = 2.38, g(2) = 2.31, and g(3) = 1.86 for 2). The cyclic voltammograms of 1 and 2 in DMF at I = 0.1 M tetraethylammonium chloride, TEACl, displayed one-electron Fe-III/II redox process at E-1/2 = - 0.04 V and + 0.05 V versus Ag/AgCl for 1 and 2, respectively. Both Fe-III complexes, 1 and 2, cleaved pUC19 DNA at 0.1 mM in the presence of H2O2. Complex 1 was found to cleave 293 base-pair DNA with a little selectivity as compared with the Fe-III-BLM complex, indicating that the metal-chelating moiety may be necessary for the sequence selectivity of DNA strand scission by BLM. (C) 1999 Elsevier Science S.A. All rights reserved.