4-肼基-6-甲氧基嘧啶 | 23905-80-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-肼基-6-甲氧基嘧啶
• 英文名称: 4-hydrazinyl-6-methoxypyrimidine
• 英文别名: (6-methoxypyrimidin-4-yl)hydrazine
• CAS: 23905-80-8
• 化学式: C₅H₈N₄O
• 分子量: 140.145
• InChiKey: IEVYUPUJSDLOID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  73.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  吡啶-2-甲醛 、 4-肼基-6-甲氧基嘧啶 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以72%的产率得到4'-methoxy-6'-(2-(pyridin-2-ylmethylene)hydrazinyl)pyrimidine
  参考文献：
  名称：

  Synthesis and characterization of the anticancer and metal binding properties of novel pyrimidinylhydrazone derivatives

  摘要：

  Three novel pyrimidinylhydrazones substituted at either the aromatic moiety or at the imine carbon atom were synthesized and characterized by standard analytical methods. All compounds were found to be toxic in the micro- to submicromolar range against a diverse panel of cancer cell lines including multidrug resistant (MDR) derivatives expressing P-glycoprotein (Pgp). UV-visible spectrophotometry experiments demonstrated that the most active compound (3) forms highly stable complexes with iron(III) and copper(II) in a wide pH range with a stronger preference towards iron(III). The redox activity of the iron and copper complexes of ligand 3 was investigated using cyclic voltammetry and was tested with cellular reductants. The impact of reactive oxygen species (ROS) on the mechanism of toxicity was assessed using the ROS-sensitive cell permeable dye 2',7'-dichlorofluorescin diacetate (DCFDA). Our results demonstrate that the studied pyrimidinylhydrazones form redox-active iron and copper complexes that are capable of producing intracellular ROS, which might lead to cellular damage and cell death in cancer cells regardless of their resistance status. (C) 2014 Published by Elsevier Inc.

  DOI：

  10.1016/j.jinorgbio.2014.12.015
• 作为产物：
  描述：

  4-氯-6-甲氧基嘧啶 在 肼 作用下， 以 甲醇 、 水 为溶剂， 生成 4-肼基-6-甲氧基嘧啶
  参考文献：
  名称：

  Synthesis and characterization of the anticancer and metal binding properties of novel pyrimidinylhydrazone derivatives

  摘要：

  Three novel pyrimidinylhydrazones substituted at either the aromatic moiety or at the imine carbon atom were synthesized and characterized by standard analytical methods. All compounds were found to be toxic in the micro- to submicromolar range against a diverse panel of cancer cell lines including multidrug resistant (MDR) derivatives expressing P-glycoprotein (Pgp). UV-visible spectrophotometry experiments demonstrated that the most active compound (3) forms highly stable complexes with iron(III) and copper(II) in a wide pH range with a stronger preference towards iron(III). The redox activity of the iron and copper complexes of ligand 3 was investigated using cyclic voltammetry and was tested with cellular reductants. The impact of reactive oxygen species (ROS) on the mechanism of toxicity was assessed using the ROS-sensitive cell permeable dye 2',7'-dichlorofluorescin diacetate (DCFDA). Our results demonstrate that the studied pyrimidinylhydrazones form redox-active iron and copper complexes that are capable of producing intracellular ROS, which might lead to cellular damage and cell death in cancer cells regardless of their resistance status. (C) 2014 Published by Elsevier Inc.

  DOI：

  10.1016/j.jinorgbio.2014.12.015

文献信息

• Metal-Free Photoredox Catalyzed Sulfonylation of Phenylhydrazines with Thiols
  作者：Ambuj Kumar Kushwaha、Arsala Kamal、Pooja Kumari、Sundaram Singh

  DOI：10.1021/acs.orglett.4c00849

  日期：2024.5.10

  a metal-free, environment-friendly photoredox-catalyzed sulfonylation of phenylhydrazines using thiols, employing MeCN:H2O as a green solvent and eosin Y as a photoredox catalyst. This strategy exhibits a broad substrate scope and good functional group compatibility, including hetero(aryl) as well as aliphatic phenylhydrazines. Finally, this protocol also demonstrated good application for the synthesis

  磺酰化方法是一种简单有效的合成磺酰胺的方法。尽管在构建磺酰胺框架方面取得了进展，但苯肼作为胺化源的潜在用途仍有待探索。在此，我们报道了一种无金属、环境友好的光氧化还原催化苯肼磺酰化反应，采用硫醇，采用MeCN:H 2 O作为绿色溶剂，曙红Y作为光氧化还原催化剂。该策略表现出广泛的底物范围和良好的官能团兼容性，包括杂（芳基）以及脂肪族苯肼。最后，该方案还证明了其在药物类似物合成中的良好应用。
• Pape, Veronika F.S.; Tóth, Szilárd; Füredi, András, European Journal of Medicinal Chemistry, 2016, vol. 117, p. 335 - 354
  作者：Pape, Veronika F.S.、Tóth, Szilárd、Füredi, András、Szebényi, Kornélia、Lovrics, Anna、Szabó, Pál、Wiese, Michael、Szakács, Gergely

  DOI：——

  日期：——