5-(4,6-diamino-1,3,5-triazin-2-yl)cytosine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 5-(4,6-diamino-1,3,5-triazin-2-yl)cytosine
• 英文别名: 6-amino-5-(4,6-diamino-1,3,5-triazin-2-yl)-1H-pyrimidin-2-one
• 化学式: C₇H₈N₈O
• 分子量: 220.194
• InChiKey: YYFAQWJWBAVCHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  158
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-(4,6-diamino-1,3,5-triazin-2-yl)cytosine 在 哌啶 、 2,2'-二硫双(5-硝基吡啶) 、 sodium hydride 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 37.0h， 生成 JanusB-Nea2
  参考文献：
  名称：

  Synthesis of Janus Compounds for the Recognition of G-U Mismatched Nucleobase Pairs

  摘要：

  The design and synthesis of two Janus-type heterocycles with the capacity to simultaneously recognize guanine and uracyl in G-U mismatched pairs through complementary hydrogen bond pairing is described. Both compounds were conveniently functionalized with a carboxylic function and efficiently attached to a tripeptide sequence by using solid-phase methodologies. Ligands based on the derivatization of guanidinylated analogue have been synthesized, and their interaction with such Janus compounds with a small aminoglycoside, neamine, and its Tau RNA has been investigated by using several biophysical techniques, including including UV-monitored melting curves, fluorescence titration experiments, and H-1 NMR The overall results indicated that Janus-neamine/guanidinoneamine showed some preference for the +3 mutated RNA sequence associated with the development of some tauopathies, although preliminary NMR studies have not confirmed binding to G-U pairs. Moreover, a good correlation has been found between the RNA binding affinity of such Janus-containing ligands and their ability to stabilize this secondary structure upon complexation.

  DOI：

  10.1021/jo401684j
• 作为产物：
  描述：

  2,2-二氰基乙烯基脲 在 sodium methylate 、 potassium hydroxide 作用下， 以 乙二醇 为溶剂， 反应 40.0h， 生成 5-(4,6-diamino-1,3,5-triazin-2-yl)cytosine
  参考文献：
  名称：

  Synthesis of Janus Compounds for the Recognition of G-U Mismatched Nucleobase Pairs

  摘要：

  The design and synthesis of two Janus-type heterocycles with the capacity to simultaneously recognize guanine and uracyl in G-U mismatched pairs through complementary hydrogen bond pairing is described. Both compounds were conveniently functionalized with a carboxylic function and efficiently attached to a tripeptide sequence by using solid-phase methodologies. Ligands based on the derivatization of guanidinylated analogue have been synthesized, and their interaction with such Janus compounds with a small aminoglycoside, neamine, and its Tau RNA has been investigated by using several biophysical techniques, including including UV-monitored melting curves, fluorescence titration experiments, and H-1 NMR The overall results indicated that Janus-neamine/guanidinoneamine showed some preference for the +3 mutated RNA sequence associated with the development of some tauopathies, although preliminary NMR studies have not confirmed binding to G-U pairs. Moreover, a good correlation has been found between the RNA binding affinity of such Janus-containing ligands and their ability to stabilize this secondary structure upon complexation.

  DOI：

  10.1021/jo401684j