2-{[N-(aminoethyl)amino]methyl}-4-{N-[2-(4-imidazolyl)ethyl]carbamoyl}-5-bromopyrimidine | 113250-62-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-{[N-(aminoethyl)amino]methyl}-4-{N-[2-(4-imidazolyl)ethyl]carbamoyl}-5-bromopyrimidine
• 英文别名: 2-[(2-aminoethylamino)methyl]-5-bromo-N-[2-(1H-imidazol-5-yl)ethyl]pyrimidine-4-carboxamide
• CAS: 113250-62-7
• 化学式: C₁₃H₁₈BrN₇O
• 分子量: 368.236
• InChiKey: URIOUUDPDOPWID-UHFFFAOYSA-N

物化性质

• 沸点：
  660.8±55.0 °C(Predicted)
• 密度：
  1.515±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  122
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  sodium triscarbonatocobaltate(III) trihydrate 、 2-{[N-(aminoethyl)amino]methyl}-4-{N-[2-(4-imidazolyl)ethyl]carbamoyl}-5-bromopyrimidine 在 HBF₄ 、 AgNO₃ 、 LiNO₃ 作用下， 以 水 为溶剂， 以25%的产率得到
  参考文献：
  名称：

  三种形式的钴 (III)-博来霉素合成类似物的合成、结构和反应性：药物的钴 (III) 螯合物引起的光诱导 DNA 损伤的拟议模式

  摘要：

  模拟抗肿瘤药物博来霉素 (BLM) 的金属结合位点的设计配体 PMAH 的三种钴 (III) 复合物已被合成和结构表征。复合物 [Co(PMA)(H 2 O)](NO 3 ) 2 (5) 在三斜空间群 P1 中结晶，a=7.608 (3) A, b=10.542 (3) A, c=13.116 (4 ) A, α=71.14 (2) o , β=74.59 (3) o , γ=81.66 (3) o , Z=2, V=957.7 (6) A 3

  DOI：

  10.1021/ja00036a036
• 作为产物：
  描述：

  组胺 以 氯仿 为溶剂， 反应 25.0h， 生成 2-{[N-(aminoethyl)amino]methyl}-4-{N-[2-(4-imidazolyl)ethyl]carbamoyl}-5-bromopyrimidine
  参考文献：
  名称：

  Characterization of a crystalline synthetic analog of copper(II)-bleomycin

  摘要：

  DOI：

  10.1021/ja00214a071

文献信息

• [Fe(PMA)]n+ (n = 1,2): good models of iron-bleomycins and examples of mononuclear non-heme iron complexes with significant oxygen-activation capabilities
  作者：Richard J. Guajardo、Samuel E. Hudson、Steven J. Brown、Pradip K. Mascharak

  DOI：10.1021/ja00071a006

  日期：1993.9

  the antitumor drug bleomycin (BLM) have been isolated and characterized by spectroscopic techniques. In both [Fe II (PMA)]Cl.MeOH (4) and [Fe III (PMA)] (NO 3 ) 2 -DMSO (5), the deprotonated PMA - framework is ligated to the metal center through five nitrogens located in the primary and secondary amines, pyrimidine and imidazole rings, and the amide moiety. The sixth coordination site on iron in these

  模拟抗肿瘤药物博来霉素 (BLM) 的金属结合部分的设计配体 PMAH 的 Fe(II) 和 Fe(III) 复合物已被分离并通过光谱技术表征。在 [Fe II (PMA)]Cl.MeOH (4) 和 [Fe III (PMA)] (NO 3 ) 2 -DMSO (5) 中，去质子化的 PMA - 骨架通过位于伯胺和仲胺、嘧啶和咪唑环以及酰胺部分。这些复合物中铁上的第六个配位点被易于替换的溶剂分子占据。这两种模型配合物的光谱和化学行为与 BLM 的 Fe(II) 和 Fe(III) 配合物的相似性强烈表明该药物使用相同的一组供体中心来结合铁
• EPR Spectroscopic Reinvestigation of the Activation of Iron Complexes of PMAH as a Bleomycin Model
  作者：István Lippai、Richard S. Magliozzo、Jack Peisach

  DOI：10.1021/ja980458p

  日期：1999.2.1

  The structure and reactivity of iron complexes of PMAH, which contains Ligands that mimic the metal binding domain of iron bleomycin (FeBLM), have been studied using EPR spectroscopy. It had been reported [Guajardo, R. J.; Hudson, S. E.; Brown, S. J.; Mascharak, P. K. J. Am. Chem. Soc. 1993, 115, 7971] that iron complexes of PMAH can be activated to a ferric hydroperoxide, a structural analog by activated BLM, by various routes, including reaction of [Fe(III)PMA](2+) with iodosylbenzene (PhIO), methanol, and base. We show that with or without PhIO, the latter reaction produces the methoxide complex of Fe(III)PMA, and not the hydroperoxide, contrary to the previous report. Thus, O-O bond formation through generation of a ferric hydroperoxide does not occur. The same methoxide complex (g = 2.28, 2.18, 1.93) is generated by the addition of organic base and CH3OH, or LiOCH3, to [Fe(III)PMA](2+). The formation of this [CH3O-Fe(III)PMA](+) complex is confirmed by EPR titration of [Fe(III)PMA](2+) with -OCH3 and by electrospray mass spectrometry. In contrast, the hydroperoxy complex of Fe(III)PMA (g = 2.22, 2.17, 1.94) can be generated by the reaction of I:Fe(III)PMA](2+) with hydrogen peroxide or during aerobic oxidation of [Fe(II)PMA](+). The present results illustrate that activation of iron complexes of PMAH occur under conditions that produce activated BLM and further demonstrate that reaction of [Fe(III)PMA](2+) with PhIO and base does not provide a route to either a hypervalent iron species or a hydroperoxide intermediate. These results agree with the finding that PhIO cannot: be used to generate activated bleomycin.
• Brown, Steven J.; Olmstead, Marilyn M.; Mascharak, Pradip K., Inorganic Chemistry, 1989, vol. 28, # 19, p. 3720 - 3728
  作者：Brown, Steven J.、Olmstead, Marilyn M.、Mascharak, Pradip K.

  DOI：——

  日期：——
• Brown, Steven J.; Hudson, Samuel E.; Stephan, Douglas W., Inorganic Chemistry, 1989, vol. 28, # 3, p. 468 - 477
  作者：Brown, Steven J.、Hudson, Samuel E.、Stephan, Douglas W.、Mascharak, Pradip K.

  DOI：——

  日期：——
• Light-induced nicking of DNA by a synthetic analog of cobalt(III)-bleomycin
  作者：Steven J. Brown、Samuel E. Hudson、Marilyn M. Olmstead、Pradip K. Mascharak

  DOI：10.1021/ja00198a080

  日期：1989.8