6-(2-Hydroxyanilino)uracil | 105147-86-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(2-Hydroxyanilino)uracil
• 英文别名: 6-(2-Hydroxyanilino)pyrimidine-2,4(1H,3H)-dione；6-(2-hydroxyanilino)-1H-pyrimidine-2,4-dione
• CAS: 105147-86-2
• 化学式: C₁₀H₉N₃O₃
• 分子量: 219.2
• InChiKey: KROCLOCEYZOUEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.5
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(2-Hydroxyanilino)uracil 在 caesium carbonate 作用下， 以 乙酸酐 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 10-<2-(Butyloxy)phenyl>-3-butylisoalloxazine
  参考文献：
  名称：

  Coenzyme models. 47. Synthesis and reactivity studies of novel flavinophanes and 5-deazaflavinophanes: correlation between flavin reactivity and ring strain

  摘要：

  DOI：

  10.1021/ja00195a055
• 作为产物：
  描述：

  6-氯尿嘧啶 、 2-氨基苯酚 生成 6-(2-Hydroxyanilino)uracil
  参考文献：
  名称：

  具有平面手性的新型脱氮黄素的合成。氧化还原引起的“跳绳”消旋

  摘要：

  合成了具有平面手性的新的5-脱氮黄素（dFl（n）），其中10-（2'-羟基）苯基中的N（3）和O（2'α）通过一条链连接（n = 8， 10）。（+）-dF1（n = 8）在通过（R）-和（S）-1,1'-bi-2-萘酚进行的荧光猝灭中显示出较大的手性区分。在环境条件下光学稳定的（+）-dF1（n = 10），仅在转变为还原形式时才消旋。这是氧化还原引起的跳绳消旋作用的第一个例子。

  DOI：

  10.1016/s0040-4039(00)84327-0

文献信息

• Synthesis of new deazaflavins with planar chirality. Redox-induced “rope-skipping” racemization
  作者：Seiji Shinkai、Toshiro Yamaguchi、Hideki Nakao、Osamu Manabe

  DOI：10.1016/s0040-4039(00)84327-0

  日期：1986.1

  New 5-deazaflavins with planar chirality (dFl(n)) were synthesized in which N(3) and O(2′α) in the 10-(2′-hydroxy)phenyl group were linked by a chain (n=8,10). (+)-dFl(n=8) showed a large chiral discrimination in fluorescence quenching by (R)- and (S)-1,1′-bi-2- naphthol. (+)-dFl(n=10), which was optically stable at ambient conditions, racemized only when it was converted to the reduced form. This

  合成了具有平面手性的新的5-脱氮黄素（dFl（n）），其中10-（2'-羟基）苯基中的N（3）和O（2'α）通过一条链连接（n = 8， 10）。（+）-dF1（n = 8）在通过（R）-和（S）-1,1'-bi-2-萘酚进行的荧光猝灭中显示出较大的手性区分。在环境条件下光学稳定的（+）-dF1（n = 10），仅在转变为还原形式时才消旋。这是氧化还原引起的跳绳消旋作用的第一个例子。
• Shinkai, Seiji; Kawase, Akito; Manabe, Osamu, Journal of the Chemical Society. Perkin transactions I, 1990, # 4, p. 1075 - 1078
  作者：Shinkai, Seiji、Kawase, Akito、Manabe, Osamu

  DOI：——

  日期：——
• SHINKAI, SEIJI;KAWASE, AKITO;MANABE, OSAMU, J. CHEM. SOC. PT 1. PERKIN TRANS.,(1990) N, C. 1075-1078
  作者：SHINKAI, SEIJI、KAWASE, AKITO、MANABE, OSAMU

  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.
• Coenzyme models. 47. Synthesis and reactivity studies of novel flavinophanes and 5-deazaflavinophanes: correlation between flavin reactivity and ring strain
  作者：Seiji Shinkai、Akito Kawase、Toshiro Yamaguchi、Osamu Manabe、Yoshikazu Wada、Fumio Yoneda、Yoshihisa Ohta、Kichisuke Nishimoto

  DOI：10.1021/ja00195a055

  日期：1989.6