(2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-4-[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxy-tetrahydropyran-2-yl]oxy-3-hydroxy-5-[[4-[[4-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]phenoxy]methyl]triazol-1-yl]methyl]tetrahydrofuran-2-yl]oxy-3-hydroxy-cyclohexoxy]tetrahydropyran-3,4-diol | 1268487-10-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-4-[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxy-tetrahydropyran-2-yl]oxy-3-hydroxy-5-[[4-[[4-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]phenoxy]methyl]triazol-1-yl]methyl]tetrahydrofuran-2-yl]oxy-3-hydroxy-cyclohexoxy]tetrahydropyran-3,4-diol
• 英文别名: (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-4-[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-3-hydroxy-5-[[4-[[4-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]phenoxy]methyl]triazol-1-yl]methyl]oxolan-2-yl]oxy-3-hydroxycyclohexyl]oxyoxane-3,4-diol
• CAS: 1268487-10-0
• 化学式: C₄₄H₆₇N₁₃O₁₃
• 分子量: 986.095
• InChiKey: KOJVIBRTYPXBJK-UOBXGQBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.2
• 重原子数：
  70
• 可旋转键数：
  15
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  408
• 氢给体数：
  13
• 氢受体数：
  24

反应信息

• 作为产物：
  描述：

  在 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 0.5h， 以20 mg的产率得到(2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-4-[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxy-tetrahydropyran-2-yl]oxy-3-hydroxy-5-[[4-[[4-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]phenoxy]methyl]triazol-1-yl]methyl]tetrahydrofuran-2-yl]oxy-3-hydroxy-cyclohexoxy]tetrahydropyran-3,4-diol
  参考文献：
  名称：

  Recognition of HIV-TAR RNA using neomycin–benzimidazole conjugates

  摘要：

  Synthesis of a novel class of compounds and their biophysical studies with TAR-RNA are presented. The synthesis of these compounds was achieved by conjugating neomycin, an aminoglycoside, with benzimidazoles modeled from a B-DNA minor groove binder, Hoechst 33258. The neomycin-benzimidazole conjugates have varying linkers that connect the benzimidazole and neomycin units. The linkers of varying length (5-23 atoms) in these conjugates contain one to three triazole units. The UV thermal denaturation experiments showed that the conjugates resulted in greater stabilization of the TAR-RNA than either neomycin or benzimidazole used in the synthesis of conjugates. These results were corroborated by the FID displacement and tat-TAR inhibition assays. The binding of ligands to the TAR-RNA is affected by the length and composition of the linker. Our results show that increasing the number of triazole groups and the linker length in these compounds have diminishing effect on the binding to TAR-RNA. Compounds that have shorter linker length and fewer triazole units in the linker displayed increased affinity towards the TAR RNA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.014

文献信息

• Recognition of HIV-TAR RNA using neomycin–benzimidazole conjugates
  作者：Nihar Ranjan、Sunil Kumar、Derrick Watkins、Deyun Wang、Daniel H. Appella、Dev P. Arya

  DOI：10.1016/j.bmcl.2013.08.014

  日期：2013.10

  Synthesis of a novel class of compounds and their biophysical studies with TAR-RNA are presented. The synthesis of these compounds was achieved by conjugating neomycin, an aminoglycoside, with benzimidazoles modeled from a B-DNA minor groove binder, Hoechst 33258. The neomycin-benzimidazole conjugates have varying linkers that connect the benzimidazole and neomycin units. The linkers of varying length (5-23 atoms) in these conjugates contain one to three triazole units. The UV thermal denaturation experiments showed that the conjugates resulted in greater stabilization of the TAR-RNA than either neomycin or benzimidazole used in the synthesis of conjugates. These results were corroborated by the FID displacement and tat-TAR inhibition assays. The binding of ligands to the TAR-RNA is affected by the length and composition of the linker. Our results show that increasing the number of triazole groups and the linker length in these compounds have diminishing effect on the binding to TAR-RNA. Compounds that have shorter linker length and fewer triazole units in the linker displayed increased affinity towards the TAR RNA. (C) 2013 Elsevier Ltd. All rights reserved.