2-amino-4-<(cyclohexylmethyl)amino>pyrimidin-6-one | 146203-13-6

• 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-amino-4-<(cyclohexylmethyl)amino>pyrimidin-6-one
• 英文别名: 2-amino-6-(cyclohexanemethylamino)-3H-pyrimidin-4-one；2-amino-4-(cyclohexylmethylamino)-1H-pyrimidin-6-one
• CAS: 146203-13-6
• 化学式: C₁₁H₁₈N₄O
• 分子量: 222.29
• InChiKey: RNZFGODGDBKATF-UHFFFAOYSA-N

物化性质

• 熔点：
  227-228 °C
• 沸点：
  390.1±45.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  79.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-4-<(cyclohexylmethyl)amino>pyrimidin-6-one 在 吡啶 、 sodium acetate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 9-(cyclohexylmethyl)-N²-((1,1,3,3-tetramethylbutyl)ureido)-7-deazaguanine
  参考文献：
  名称：

  Higher Affinity Quadruply Hydrogen-Bonded Complexation with 7-Deazaguanine Urea

  摘要：

  UG forms a highly stable quadruply hydrogen-bonded heterocomplex with DAN, but the fidelity of the complex is lowered somewhat by the Hoogsteen-side oligornerization of UG (K-assoc similar to 230 M-1, CDCl3). DeUG was prepared as a more robust analogue of UG lacking the Hoogsteen nitrogen atom. Remarkably, the deaza analogue, DeUG, forms a much more stable complex with DAN (> 10-fold higher K-assoc for DeUG.DAN vs UG.DAN) but also dimerizes more strongly (K-dim = 880 +/- 40 M-1, CDCl3) by adopting a conformation preorganized for both binding and dimerization.

  DOI：

  10.1021/ol0601803
• 作为产物：
  描述：

  环己甲胺 在 sodium hydroxide 、 N,N-二异丙基乙胺 作用下， 以 乙二醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 2-amino-4-<(cyclohexylmethyl)amino>pyrimidin-6-one
  参考文献：
  名称：

  Higher Affinity Quadruply Hydrogen-Bonded Complexation with 7-Deazaguanine Urea

  摘要：

  UG forms a highly stable quadruply hydrogen-bonded heterocomplex with DAN, but the fidelity of the complex is lowered somewhat by the Hoogsteen-side oligornerization of UG (K-assoc similar to 230 M-1, CDCl3). DeUG was prepared as a more robust analogue of UG lacking the Hoogsteen nitrogen atom. Remarkably, the deaza analogue, DeUG, forms a much more stable complex with DAN (> 10-fold higher K-assoc for DeUG.DAN vs UG.DAN) but also dimerizes more strongly (K-dim = 880 +/- 40 M-1, CDCl3) by adopting a conformation preorganized for both binding and dimerization.

  DOI：

  10.1021/ol0601803

文献信息

• Nucleosides. 5. Synthesis of guanine and formycin B derivatives as potential inhibitors of purine nucleoside phosphorylase
  作者：Ji Wang Chern、Horng Yuh Lee、Chien Shu Chen、Donna S. Shewach、Peter E. Daddona、Leroy B. Townsend

  DOI：10.1021/jm00060a010

  日期：1993.4

  In an effort to develop potent human purine nucleoside phosphorylase (PNP) inhibitors as immunosuppressive and chemotherapeutic agents, several 8-aminoguanine derivatives were synthesized and evaluated as potential PNP inhibitors. These studies were designed to investigate the hydrophobic effect of a substituent on the N-9 of the purine heterocycle and/or the C-5' positions. Compounds such as 8-aminoguanosine

  为了开发有效的人嘌呤核苷磷酸化酶（PNP）抑制剂作为免疫抑制剂和化学治疗剂，合成了几种8-氨基鸟嘌呤衍生物并将其评估为潜在的PNP抑制剂。这些研究旨在研究取代基对嘌呤杂环的N-9和/或C-5'位置的疏水作用。合成了含有对-（氟磺酰基）苯甲酰基部分的化合物，例如8-氨基鸟苷，鸟苷，甲霉素B和8-氨基无环鸟苷。确定了这些化合物对红细胞PNP的亲和力，并且这些化合物均未显示出比母体化合物更好的亲和力。但是，我们发现在N-9和C-5'位置的疏水作用可能在与PNP活性位点结合中起重要作用。因此，8-amino-5'
• Hydrogen-Bonded DeUG·DAN Heterocomplex: Structure and Stability and a Scalable Synthesis of DeUG with Reactive Functionality
  作者：Darrell W. Kuykendall、Cyrus A. Anderson、Steven C. Zimmerman

  DOI：10.1021/ol802344w

  日期：2009.1.1

  A convenient, scalable synthesis of the supramolecular building block 7-deazaguanine-based urea (DeUG) is reported. Incorporation of reactive moieties (DeUG azide 10 and alkyne 11 for copper-catalyzed azide-alkyne cycloadditions, "click chemistry") and a demonstration of transesterification (DeUG glycol, 12) highlights the versatility. X-ray structures of DeUG and a DeUG-DAN heterocomplex were obtained. K-assoc for the 1.2 heterocomplex was estimated to be 2 x 10(8) M-1 in chloroform.
• Higher Affinity Quadruply Hydrogen-Bonded Complexation with 7-Deazaguanine Urea
  作者：Hugo C. Ong、Steven C. Zimmerman

  DOI：10.1021/ol0601803

  日期：2006.4.1

  UG forms a highly stable quadruply hydrogen-bonded heterocomplex with DAN, but the fidelity of the complex is lowered somewhat by the Hoogsteen-side oligornerization of UG (K-assoc similar to 230 M-1, CDCl3). DeUG was prepared as a more robust analogue of UG lacking the Hoogsteen nitrogen atom. Remarkably, the deaza analogue, DeUG, forms a much more stable complex with DAN (> 10-fold higher K-assoc for DeUG.DAN vs UG.DAN) but also dimerizes more strongly (K-dim = 880 +/- 40 M-1, CDCl3) by adopting a conformation preorganized for both binding and dimerization.