epi-5-N[[[αN-(9-fluorenylmethyloxycarbonyl)-γN-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)]arginyl]aminoethyl]-1,3,2',6'-tetraazido neamine | 1159108-05-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: epi-5-N[[[αN-(9-fluorenylmethyloxycarbonyl)-γN-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)]arginyl]aminoethyl]-1,3,2',6'-tetraazido neamine
• 英文别名: epi-5-N[[[αN-(9-fluorenylmethyloxycarbonyl)-GN-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)]arginyl]aminoethyl]-1,3,2',6'-tetraazido neamine
• CAS: 1159108-05-0
• 化学式: C₄₈H₆₂N₁₈O₁₁S
• 分子量: 1099.2
• InChiKey: RWVYSIMVJQFHAA-XVGFAGLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.83
• 重原子数：
  78.0
• 可旋转键数：
  21.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  444.93
• 氢给体数：
  9.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  epi-5-N[[[αN-(9-fluorenylmethyloxycarbonyl)-γN-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)]arginyl]aminoethyl]-1,3,2',6'-tetraazido neamine 在 二乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以85%的产率得到epi-5-N[[[γN-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)]arginyl]aminoethyl]-1,3,2',6'-tetraazido neamine
  参考文献：
  名称：

  Synthesis and evaluation of novel neamine derivatives effectively targeting to RNA

  摘要：

  Three new derivatives of neamine, 3 (NE), 6 (NEA) and 9 (NEL), were synthesized by connecting arginine or lysine to 5-hydroxyl group of neamine using ethylenediamine as a linker. The binding affinities of these derivatives to A site of 16S RNA and TAR RNA indicate that the modi. cation on 5-hydroxyl of neamine by amino acid can enhance the binding affinity of neamine. Compound 9 (NEL) shows some antibacterial activities. These results demonstrate that modi. cation on 5-hydroxyl group of neamine may provide a promising way for the development of potential candidates effectively targeting to RNAs. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.021
• 作为产物：
  描述：

  epi-5-(2-aminoethyl)-amino-1,3,2',6'-tetraazido neamine 、 Fmoc-Pbf-L-精氨酸 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 以79%的产率得到epi-5-N[[[αN-(9-fluorenylmethyloxycarbonyl)-γN-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)]arginyl]aminoethyl]-1,3,2',6'-tetraazido neamine
  参考文献：
  名称：

  Synthesis and evaluation of novel neamine derivatives effectively targeting to RNA

  摘要：

  Three new derivatives of neamine, 3 (NE), 6 (NEA) and 9 (NEL), were synthesized by connecting arginine or lysine to 5-hydroxyl group of neamine using ethylenediamine as a linker. The binding affinities of these derivatives to A site of 16S RNA and TAR RNA indicate that the modi. cation on 5-hydroxyl of neamine by amino acid can enhance the binding affinity of neamine. Compound 9 (NEL) shows some antibacterial activities. These results demonstrate that modi. cation on 5-hydroxyl group of neamine may provide a promising way for the development of potential candidates effectively targeting to RNAs. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.021

文献信息

• Synthesis and biological evaluation of novel neamine–nucleoside conjugates potentially targeting to RNAs
  作者：Yanli Xu、Hongwei Jin、Zhenjun Yang、Liangren Zhang、Lihe Zhang

  DOI：10.1016/j.tet.2009.04.084

  日期：2009.7

  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.