epi-5-(2-aminoethyl)-amino-1,3,2',6'-tetraazido neamine | 948916-00-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: epi-5-(2-aminoethyl)-amino-1,3,2',6'-tetraazido neamine
• CAS: 948916-00-5
• 化学式: C₁₄H₂₄N₁₄O₅
• 分子量: 468.435
• InChiKey: OLUJAHRTBSOPOF-NMILMINPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.15
• 重原子数：
  33.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  312.24
• 氢给体数：
  5.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  epi-5-(2-aminoethyl)-amino-1,3,2',6'-tetraazido neamine 在 吡啶 、 硫化氢 、 三乙胺 作用下， 以 水 为溶剂， 反应 1.0h， 生成 Nea-Eda
  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：

  、 乙二胺 生成 epi-5-(2-aminoethyl)-amino-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

• Studies on the synthesis of neamine-dinucleosides and neamine-PNA conjugates and their interaction with RNA
  作者：Hui Mei、Lei Xing、Li Cai、Hong-Wei Jin、Peng Zhao、Zhen-Jun Yang、Liang-Ren Zhang、Li-He Zhang

  DOI：10.1016/j.bmcl.2008.09.062

  日期：2008.10

  neamine-dinucleotide conjugates 8a-g and neamine-PNA conjugates 12a-c and 14a-d, were synthesized. Compound 8a-g were synthesized by the condensation of azido-neamine with dinucleotide-5'-carboxylic acids, followed by reduction and deprotection. Compound 12a-c and 14a-d were synthesized by the similar strategy. The binding affinities of conjugates 8a-g, 12a-c, and 14a-d towards 16S RNA, 18S RNA, and TAR RNA were evaluated

  合成了两种类型的神经胺衍生物，即神经胺-二核苷酸缀合物8a-g和神经胺-PNA缀合物12a-c和14a-d。通过叠氮基-亚胺与二核苷酸-5'-羧酸的缩合，然后还原和脱保护，来合成化合物8a-g。通过相似的策略合成化合物12a-c和14a-d。通过SPR评估缀合物8a-g，12a-c和14a-d对16S RNA，18S RNA和TAR RNA的结合亲和力。这表明缀合物12a-c和14a-d以与神经胺相同的水平与16S，18S RNA相互作用，与神经胺相比，14a和14d显示出对TAR RNA的约两倍的结合亲和力。但是，神经胺二核苷酸共轭物8a-g对16S，18S和TAR RNA的结合亲和力很弱，
• 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.
• Synthesis of aminodisaccharide–nucleoside conjugates for RNA binding
  作者：Li Cai、Qin Li、Bo Ren、Zhen-Jun Yang、Liang-Ren Zhang、Li-He Zhang

  DOI：10.1016/j.tet.2007.06.002

  日期：2007.8

  Two types of aminodisaccharide-nucleoside conjugates were synthesized by the condensation of azidodisaccharide and nucleoside using aliphatic diamine as a linker. The corresponding azidodisaccharides could be yielded from neamine in good yield. The binding properties to 16S RNA of these conjugates were evaluated by SPR. It was found that the nucleobase played a significant role in the binding of these conjugates to 16S RNA and a shorter linker between the aminodisaccharide and nucleoside was favorable for 16S RNA binding. (c) 2007 Elsevier Ltd. All rights reserved.