(R)-2-Amino-N-{6-[(1R,2R,3S,5R,6S)-3,5-diamino-2-((2R,3R,4R,5S,6R)-3-amino-6-aminomethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-6-hydroxy-cyclohexyloxy]-hexyl}-3-(1H-imidazol-4-yl)-propionamide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2-Amino-N-{6-[(1R,2R,3S,5R,6S)-3,5-diamino-2-((2R,3R,4R,5S,6R)-3-amino-6-aminomethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-6-hydroxy-cyclohexyloxy]-hexyl}-3-(1H-imidazol-4-yl)-propionamide
• 英文别名: (2R)-2-amino-N-[6-[(1R,2R,3S,5R,6S)-3,5-diamino-2-[(2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxy-tetrahydropyran-2-yl]oxy-6-hydroxy-cyclohexoxy]hexyl]-3-(1H-imidazol-4-yl)propanamide；(2R)-2-amino-N-[6-[(1R,2R,3S,5R,6S)-3,5-diamino-2-[(2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-6-hydroxycyclohexyl]oxyhexyl]-3-(1H-imidazol-5-yl)propanamide
• 化学式: C₂₄H₄₆N₈O₇
• 分子量: 558.679
• InChiKey: SKWZCPDPYNBHAW-LCZNQVJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.8
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  276
• 氢给体数：
  10
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 苯甲醚 为溶剂， 反应 12.0h， 生成 (R)-2-Amino-N-{6-[(1R,2R,3S,5R,6S)-3,5-diamino-2-((2R,3R,4R,5S,6R)-3-amino-6-aminomethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-6-hydroxy-cyclohexyloxy]-hexyl}-3-(1H-imidazol-4-yl)-propionamide
  参考文献：
  名称：

  A route for preparing new neamine derivatives targeting HIV-1 TAR RNA

  摘要：

  In the search for molecules possessing antibiotic or antiviral properties and ribonuclease like activity, that is, able to induce the cleavage of bacterial or viral RNA targets, we report a new route for preparing selectively neamine derivatives modified at their 4- and/or 5-hydroxyl functions. Using trityl protective groups for the amino functions and 4-methoxybenzyl groups for the hydroxyl functions, new neamine derivatives, such as histidine, phenanthroline, flavin, adenine conjugates were efficiently obtained after a single deprotection step under acid conditions. For the first time, 4-modified neamine derivatives were prepared. Most of the 4'-derivatives showed affinity and selectivity for TAR RNA close to those of the corresponding 5-derivatives. The most potent compound is the 4'-histidine derivative 31 which binds more tightly to TAR RNA compared to its 5-isomer and neamine and recognizes selectively TAR oligonucleotides having a bulge. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.122

文献信息

• A route for preparing new neamine derivatives targeting HIV-1 TAR RNA
  作者：Emmanuel Riguet、Jérôme Désiré、Christian Bailly、Jean-Luc Décout

  DOI：10.1016/j.tet.2004.06.122

  日期：2004.9

  In the search for molecules possessing antibiotic or antiviral properties and ribonuclease like activity, that is, able to induce the cleavage of bacterial or viral RNA targets, we report a new route for preparing selectively neamine derivatives modified at their 4- and/or 5-hydroxyl functions. Using trityl protective groups for the amino functions and 4-methoxybenzyl groups for the hydroxyl functions, new neamine derivatives, such as histidine, phenanthroline, flavin, adenine conjugates were efficiently obtained after a single deprotection step under acid conditions. For the first time, 4-modified neamine derivatives were prepared. Most of the 4'-derivatives showed affinity and selectivity for TAR RNA close to those of the corresponding 5-derivatives. The most potent compound is the 4'-histidine derivative 31 which binds more tightly to TAR RNA compared to its 5-isomer and neamine and recognizes selectively TAR oligonucleotides having a bulge. (C) 2004 Elsevier Ltd. All rights reserved.