(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-N-[(2S)-1-[2-[[(1S,2R,3S,5R,6S)-3,5-diamino-2-[(2S,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-6-hydroxycyclohexyl]amino]ethylamino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]-3,4-dihydroxyoxolane-2-carboxamide | 1174010-18-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: (2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-N-[(2S)-1-[2-[[(1S,2R,3S,5R,6S)-3,5-diamino-2-[(2S,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-6-hydroxycyclohexyl]amino]ethylamino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]-3,4-dihydroxyoxolane-2-carboxamide
• CAS: 1174010-18-4
• 化学式: C₃₀H₅₃N₁₅O₁₀
• 分子量: 783.845
• InChiKey: NJRCURBWZJGKHA-KZHHCRMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.7
• 重原子数：
  55
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  437
• 氢给体数：
  15
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-N-[(2S)-1-[2-[[(1S,2R,3S,5R,6S)-3,5-diamino-2-[(2S,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-6-hydroxycyclohexyl]amino]ethylamino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]-3,4-dihydroxyoxolane-2-carboxamide 、 三氟乙酸 以 甲醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of novel neamine–nucleoside conjugates potentially targeting to RNAs

  摘要：

  Eighteen novel neamine-nucleoside conjugates with ethylenediamine-lysine or ethylenediamine-arginine as the linker were synthesized and their potential binding to A site of 16S RNA and TAR RNA was evaluated using SPR (surface plasmon resonance). Compared with neamine, compounds 10i and 10q show 6.3 and 4.8 times potential in binding to A site of 16S RNA and eight and six times potential in binding to TAR RNA, respectively. According to the data of SPR, it indicates that amino acid residue and nucleobase moieties of the designed neamine-nucleosides conjugates exhibit the important contributions for the binding to A site of 16S RNA and TAR RNA. The molecular docking Study on the interaction between the ligands and A site of 16S RNA is in agreement with the experimental data. The novel type of modification may provide a promising way for the development of neamine derivatives effectively targeting to RNAs. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.084
• 作为产物：
  描述：

  在 吡啶 、 硫化氢 、 三乙胺 作用下， 以 水 为溶剂， 反应 1.0h， 生成 (2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-N-[(2S)-1-[2-[[(1S,2R,3S,5R,6S)-3,5-diamino-2-[(2S,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-6-hydroxycyclohexyl]amino]ethylamino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]-3,4-dihydroxyoxolane-2-carboxamide
  参考文献：
  名称：

  Synthesis and biological evaluation of novel neamine–nucleoside conjugates potentially targeting to RNAs

  摘要：

  Eighteen novel neamine-nucleoside conjugates with ethylenediamine-lysine or ethylenediamine-arginine as the linker were synthesized and their potential binding to A site of 16S RNA and TAR RNA was evaluated using SPR (surface plasmon resonance). Compared with neamine, compounds 10i and 10q show 6.3 and 4.8 times potential in binding to A site of 16S RNA and eight and six times potential in binding to TAR RNA, respectively. According to the data of SPR, it indicates that amino acid residue and nucleobase moieties of the designed neamine-nucleosides conjugates exhibit the important contributions for the binding to A site of 16S RNA and TAR RNA. The molecular docking Study on the interaction between the ligands and A site of 16S RNA is in agreement with the experimental data. The novel type of modification may provide a promising way for the development of neamine derivatives effectively targeting to RNAs. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.04.084