6-cyclohexylaminouracil | 6702-72-3

• 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: 6-cyclohexylaminouracil
• 英文别名: 6-(cyclohexylamino)-1H-pyrimidine-2,4-dione
• CAS: 6702-72-3
• 化学式: C₁₀H₁₅N₃O₂
• 分子量: 209.248
• InChiKey: BLMAMCMBWRAEOF-UHFFFAOYSA-N

物化性质

• 溶解度：
  13.1 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  70.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-cyclohexylaminouracil 生成 3.3-Pentamethylen-6.8-dioxo-5.6.7.8-tetrahydro-3H-pyrimido<5.4-c>-1.2.5-oxadiazin
  参考文献：
  名称：

  Goldner,H. et al., Justus Liebigs Annalen der Chemie, 1966, vol. 692, p. 134 - 150

  摘要：

  DOI：
• 作为产物：
  描述：

  6-氯尿嘧啶 、 环己胺 反应 0.58h， 以88%的产率得到6-cyclohexylaminouracil
  参考文献：
  名称：

  在聚焦微波辐射下氟尿嘧啶与硒，硫，氧和氮亲核试剂反应合成取代的尿嘧啶

  摘要：

  在微波辐射下，氟脲与硒，硫，氧和氮亲核试剂的亲核取代反应在几分钟内完成，收率高达99％。使用微波辐射的方法优于在常规加热过程下进行的方法。

  DOI：

  10.1016/j.tet.2005.01.085

文献信息

• Synthesis of substituted uracils by the reactions of halouracils with selenium, sulfur, oxygen and nitrogen nucleophiles under focused microwave irradiation
  作者：Woei-Ping Fang、Yuh-Tsyr Cheng、Yann-Ru Cheng、Yie-Jia Cherng

  DOI：10.1016/j.tet.2005.01.085

  日期：2005.3

  Under microwave irradiation, the nucleophilic substitution reactions of halouracils with selenium, sulfur, oxygen and nitrogen nucleophiles was complete within several minutes with yields up to 99%. The method using microwave irradiation is superior to those conducted under conventional heating processes.

  在微波辐射下，氟脲与硒，硫，氧和氮亲核试剂的亲核取代反应在几分钟内完成，收率高达99％。使用微波辐射的方法优于在常规加热过程下进行的方法。
• Goldner,H. et al., Justus Liebigs Annalen der Chemie, 1966, vol. 692, p. 134 - 150
  作者：Goldner,H. et al.

  DOI：——

  日期：——
• Toxoflavins and Deazaflavins as the First Reported Selective Small Molecule Inhibitors of Tyrosyl-DNA Phosphodiesterase II
  作者：Ali Raoof、Paul Depledge、Niall M. Hamilton、Nicola S. Hamilton、James R. Hitchin、Gemma V. Hopkins、Allan M. Jordan、Laura A. Maguire、Alison E. McGonagle、Daniel P. Mould、Mathew Rushbrooke、Helen F. Small、Kate M. Smith、Graeme J. Thomson、Fabrice Turlais、Ian D. Waddell、Bohdan Waszkowycz、Amanda J. Watson、Donald J. Ogilvie

  DOI：10.1021/jm400568p

  日期：2013.8.22

  The recently discovered enzyme tyrosyl-DNA phosphodiesterase 2 (TDP2) has been implicated in the topoisomerase-mediated repair of DNA damage. In the clinical setting, it has been hypothesized that TDP2 may mediate drug resistance to topoisomerase II (topo II) inhibition by etoposide. Therefore, selective pharmacological inhibition of TDP2 is proposed as a novel approach to overcome intrinsic or acquired resistance to topo II-targeted drug therapy. Following a high-throughput screening (HTS) campaign, toxoflavins and deazaflavins were identified as the first reported sub-micromolar and selective inhibitors of this enzyme. Toxoflavin derivatives appeared to exhibit a clear structure-activity relationship (SAP.) for TDP2 enzymatic inhibition. However, we observed a key redox liability of this series, and this, alongside early in vitro drug metabolism and pharmacokinetics (DMPK) issues, precluded further exploration. The deazaflavins were developed from a singleton HTS hit. This series showed distinct SAR and did not display redox activity; however low cell permeability proved to be a challenge.