6-(1-methylhydrazino)uracil | 68558-26-9

• 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-(1-methylhydrazino)uracil
• 英文别名: 6-(1-Methylhydrazino)-2,4-pyrimidinediol；6-[amino(methyl)amino]-1H-pyrimidine-2,4-dione
• CAS: 68558-26-9
• 化学式: C₅H₈N₄O₂
• 分子量: 156.144
• InChiKey: QWORRGCLMAIWHJ-UHFFFAOYSA-N

物化性质

• 熔点：
  284-285 °C (decomp)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  87.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(1-methylhydrazino)uracil 以37%的产率得到
  参考文献：
  名称：

  WAID K.; BREITMAIER E., SYNTHESIS, 1978, NO 10, 748-749

  摘要：

  DOI：
• 作为产物：
  描述：

  6-氯尿嘧啶 、 甲基肼 以 乙醇 为溶剂， 反应 2.0h， 以94%的产率得到6-(1-methylhydrazino)uracil
  参考文献：
  名称：

  Syntheses and properties of 4-deazatoxoflavins and related compounds.

  摘要：

  将6-(1-甲基肼基)尿嘧啶(I)与苯乙烯溴化物在甲氧基乙醇中反应，得到相应的3-芳基-1-甲基吡啶并[4, 5-c]吡唑-5, 7(1H, 6H)-二酮（3-芳基-6-去甲基-4-去氢氧类黄素)(II)和3-芳基-5, 7-二氧基-1-甲基-1, 4, 5, 6, 7-五氢吡啶并[4, 3-c][1, 2, 4]三嗪(III)。用碘甲烷对II和III进行甲基化反应，得到相应的3-芳基-4-去氢氧类黄素(IV)和1, 6-二甲基-5, 7-二氧吡啶并[4, 3-c][1, 2, 4]三嗪(V)。IV与对氯过苯甲酸在氯仿中反应，生成相应的3-芳基-4, 4a-环氧-4-去氢氧类黄素(VI)。从动力学和合成的角度比较了II对醇的氧化能力与IV的氧化能力。IV与30%水合苛性碱反应，专一性地生成4, 8-二氢-4-去氢氧类黄素(VII)和4, 8-二氢-4-去氢氧类黄素-4-酮(VIII)，该反应通过最初形成的4-羟基-4, 8-二氢-4-去氢氧类黄素(IX)与未改变的IV之间的分子间氧化还原反应进行。VI与10%水合氢氧化钠反应，得到6-芳基-4-羟基-2-甲基吡嗪-3(2H)-酮(X)。

  DOI：

  10.1248/cpb.30.172

文献信息

• AUTORECYCLING OXIDATION OF AMINES TO CARBONYL COMPOUNDS CATALYZED BY 3,4-DISUBSTITUTED 4-DEAZATOXOFLAVIN DERIVATIVES
  作者：Tomohisa Nagamatsu、Yuko Hashiguchi、Yoshiharu Sakuma、Fumio Yoneda

  DOI：10.1246/cl.1982.1309

  日期：1982.9.5

  3,4-Disubstituted 4-deazatoxoflavin derivatives (II) were prepared by the condensation of 6-(1-methylhydrazino)uracils (I) with appropriate α-diketones. The compounds II oxidized long-chain alkylamines such as n-octylamine and n-dodecylamine besides benzylamine and cyclohexylamine to yield the corresponding carbonyl compounds via imines, catalytically with a markedly high turnover number.

  3,4-二取代的 4-脱氮氧代黄素衍生物 (II) 是通过 6-(1-甲基肼基) 尿嘧啶 (I) 与适当的 α-二酮缩合制备的。除了苄胺和环己胺外，化合物II氧化长链烷基胺如正辛胺和正十二胺，通过亚胺产生相应的羰基化合物，催化转化率显着高。
• Microwave-assisted synthesis of 3-aryl-pyrimido[5,4-e][1,2,4]triazine-5,7(1H,6H)-dione libraries: derivatives of toxoflavin
  作者：Nick Todorovic、Andrew Giacomelli、John A. Hassell、Christopher S. Frampton、Alfredo Capretta

  DOI：10.1016/j.tetlet.2010.09.044

  日期：2010.11

  The parallel synthesis of a library of toxoflavin derivatives is described. The microwave-assisted approach involves the de novo generation of the heterocyclic scaffold and allows for facile introduction of a variety of fragments.

  描述了一种平行合成的毒素类黄素衍生物的文库。微波辅助方法涉及从头产生杂环支架，并允许容易地引入各种片段。
• 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.
• Sakuma, Yoshiharu; Nagamatsu, Tomohisa; Hashiguchi, Yuko, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 3, p. 851 - 859
  作者：Sakuma, Yoshiharu、Nagamatsu, Tomohisa、Hashiguchi, Yuko、Yoneda, Fumio

  DOI：——

  日期：——
• NAGAMATSU, TOMOHISA;HASHIGUCHI, YUKO;SAKUMA, YOSHIHARU;YONEDA, FUMIO, CHEM. LETT., 1982, N 9, 1309-1312
  作者：NAGAMATSU, TOMOHISA、HASHIGUCHI, YUKO、SAKUMA, YOSHIHARU、YONEDA, FUMIO

  DOI：——

  日期：——