4,5,6-trichloro-2-{[(dimethylamino)methylidene]amino}pyrimidine | 1195949-91-7

• 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: 4,5,6-trichloro-2-{[(dimethylamino)methylidene]amino}pyrimidine
• 英文别名: 4,5,6-Trichloro-2-{[(dimethylamino)methylidene]amino}pyrimidine；N,N-dimethyl-N'-(4,5,6-trichloropyrimidin-2-yl)methanimidamide
• CAS: 1195949-91-7
• 化学式: C₇H₇Cl₃N₄
• 分子量: 253.518
• InChiKey: PMPGNUZOBPJARF-UHFFFAOYSA-N

物化性质

• 熔点：
  >260 °C
• 沸点：
  368.7±52.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  41.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5,6-trichloro-2-{[(dimethylamino)methylidene]amino}pyrimidine 在 盐酸 作用下， 以 水 为溶剂， 反应 96.0h， 以46%的产率得到2-氨基-4,5,6-三氯嘧啶
  参考文献：
  名称：

  Syntheses of 2-amino-4,6-dichloro-5-nitropyrimidine and 2-amino-4,5,6-trichloropyrimidine: an unusual aromatic substitution

  摘要：

  2-Amino-4,6-dichloro-5-nitropyrimidine is an intermediate required for the preparation of nitropyrimidines as inactivators of the DNA repairing protein MGMT. When attempting its synthesis, 2-amino-4,5,6-trichloropyrimidine is obtained instead, via unusual aromatic substitution of the nitro group in 2-amino-4-hydroxy-5-nitropyrimidin-6-one by chloride. The synthesis, the reactivity of 4,5,6-trichloropyrimidine and the efficient preparation of 2-amino-4,6-dichloro-5-nitropyrimidine are presented. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.08.029
• 作为产物：
  描述：

  (氯亚甲基)二甲基氯化铵 、 2-氨基-4,6-二羟基-5-硝基嘧啶 在 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 1.0h， 以41%的产率得到4,5,6-trichloro-2-{[(dimethylamino)methylidene]amino}pyrimidine
  参考文献：
  名称：

  Syntheses of 2-amino-4,6-dichloro-5-nitropyrimidine and 2-amino-4,5,6-trichloropyrimidine: an unusual aromatic substitution

  摘要：

  2-Amino-4,6-dichloro-5-nitropyrimidine is an intermediate required for the preparation of nitropyrimidines as inactivators of the DNA repairing protein MGMT. When attempting its synthesis, 2-amino-4,5,6-trichloropyrimidine is obtained instead, via unusual aromatic substitution of the nitro group in 2-amino-4-hydroxy-5-nitropyrimidin-6-one by chloride. The synthesis, the reactivity of 4,5,6-trichloropyrimidine and the efficient preparation of 2-amino-4,6-dichloro-5-nitropyrimidine are presented. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.08.029

文献信息

• Towards more specific O6-methylguanine-DNA methyltransferase (MGMT) inactivators
  作者：Sergio Lopez、Geoffrey P. Margison、R. Stanley McElhinney、Alessandra Cordeiro、T. Brian H. McMurry、Isabel Rozas

  DOI：10.1016/j.bmc.2011.01.038

  日期：2011.3

  Searching for a novel family of inactivators of the human DNA repair protein O-6-methylguanine-DNA methyltransferase (MGMT) which is known to bind to the DNA minor groove, we have computationally modelled and synthesised two series of 2-amino-6-aryloxy-5-nitropyrimidines with morpholino or aminodiaryl substituents (potential minor groove binders) at the 4-position. Synthesis of these compounds was achieved by successive substitution of each of the two Cl atoms of 2-amino-4,6-dichloro-nitropyrimidine by the corresponding amino and aryloxy derivatives. Biochemical evaluation of these compounds as MGMT inactivators showed poor activities, but in general the 4-bromothenyloxy derivatives showed better inactivation than the benzyloxy versions. DNA binding assessment was not possible due to insolubility problems. (C) 2011 Elsevier Ltd. All rights reserved.