2-(methylthio)-1,4,5,6-tetrahydropyrimidin-5-ol hydrochloride | 1178880-45-9

• 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: 2-(methylthio)-1,4,5,6-tetrahydropyrimidin-5-ol hydrochloride
• CAS: 1178880-45-9
• 化学式: C₅H₁₀N₂OS*ClH
• 分子量: 182.674
• InChiKey: WNMHPTZORXCIGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.09
• 重原子数：
  10.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  44.62
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(methylthio)-1,4,5,6-tetrahydropyrimidin-5-ol hydrochloride 在 一水合肼 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 4.5h， 以78.9%的产率得到2-hydrazinyl-1,4,5,6-tetrahydropyrimidin-5-ol dihydrochloride
  参考文献：
  名称：

  Synthesis and DNA cleavage activity of 2-hydrazinyl-1,4,5,6-tetrahydropyrimidine containing hydroxy group

  摘要：

  2-Hydrazinyl-1,4,5,6-tetrahydropyrimidin-5-ol dihydrochloride 2, as well as 2-hydrazinyl-4,5-dihydro-1H-imidazole dihydrochloride 1, was synthesized as metal-free DNA cleaving agent. Agarose gel electrophoresis was used to assess the plasmid pUC 19 DNA cleavage activities in the presence of 1 and 2. DNA cleavage efficiency of 2 exhibits remarkable increases compared with its corresponding non-hydroxy compound 1. Kinetic data of DNA cleavage promoted by 2 fit to the Michaelis-Menten-type equation with k(max) of 0.0378 +/- 0.0013 h (1)giving 10(6)-fold rate acceleration over uncatalyzed DNA. The acceleration is driven by the spatial proximity of the nucleophilic hydroxy group and the electrophilic activation for the phosphodiester by the ammonium and/or guanidinium groups. In vitro cytotoxic activities toward Hela cells and human leukemia HL-60 cells were also examined, and 2 exhibits stronger cytotoxic activities than 1. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2009.05.044
• 作为产物：
  描述：

  甲醇 、 5-羟基-四氢嘧啶-2(1H)-硫酮 在 盐酸 作用下， 以 水 为溶剂， 反应 24.0h， 以65.3%的产率得到2-(methylthio)-1,4,5,6-tetrahydropyrimidin-5-ol hydrochloride
  参考文献：
  名称：

  Synthesis and DNA cleavage activity of 2-hydrazinyl-1,4,5,6-tetrahydropyrimidine containing hydroxy group

  摘要：

  2-Hydrazinyl-1,4,5,6-tetrahydropyrimidin-5-ol dihydrochloride 2, as well as 2-hydrazinyl-4,5-dihydro-1H-imidazole dihydrochloride 1, was synthesized as metal-free DNA cleaving agent. Agarose gel electrophoresis was used to assess the plasmid pUC 19 DNA cleavage activities in the presence of 1 and 2. DNA cleavage efficiency of 2 exhibits remarkable increases compared with its corresponding non-hydroxy compound 1. Kinetic data of DNA cleavage promoted by 2 fit to the Michaelis-Menten-type equation with k(max) of 0.0378 +/- 0.0013 h (1)giving 10(6)-fold rate acceleration over uncatalyzed DNA. The acceleration is driven by the spatial proximity of the nucleophilic hydroxy group and the electrophilic activation for the phosphodiester by the ammonium and/or guanidinium groups. In vitro cytotoxic activities toward Hela cells and human leukemia HL-60 cells were also examined, and 2 exhibits stronger cytotoxic activities than 1. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2009.05.044