(2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2R)-3-[4-[[(2R)-3-[(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]oxy-2-hydroxypropyl]-methylamino]butyl-methylamino]-2-hydroxypropoxy]-3-hydroxycyclohexyl]oxyoxane-3,4-diol

• 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-[(2R)-3-[4-[[(2R)-3-[(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]oxy-2-hydroxypropyl]-methylamino]butyl-methylamino]-2-hydroxypropoxy]-3-hydroxycyclohexyl]oxyoxane-3,4-diol
• 化学式: C₃₆H₇₆N₁₀O₁₄
• 分子量: 873.058
• InChiKey: NVTAOQRIEMRLHK-ZWHIGZPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -10.3
• 重原子数：
  60
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  432
• 氢给体数：
  16
• 氢受体数：
  24

反应信息

• 作为产物：
  描述：

  (2R,2'R)-3,3'-(butane-1,4-diylbis(methylazanediyl))bis(1-(((1R,2R,3S,5R,6S)-3,5-diazido-2-(((2R,3R,4R,5R,6R)-3-azido-6-(azidomethyl)-4,5-bis(benzyloxy)tetrahydro-2H-pyran-2-yl)oxy)-6-(benzyloxy)cyclohexyl)oxy)propan-2-ol) 在 palladium dihydroxide 氢气 、 溶剂黄146 作用下， 生成 (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2R)-3-[4-[[(2R)-3-[(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]oxy-2-hydroxypropyl]-methylamino]butyl-methylamino]-2-hydroxypropoxy]-3-hydroxycyclohexyl]oxyoxane-3,4-diol
  参考文献：
  名称：

  Structure–activity relationships of bivalent aminoglycosides and evaluation of their microbiological activities

  摘要：

  A library of 4,5- and 4,6-linked bivalent aminoglycoside (AMG) antibiotics consisting of neamine and nebramine pharmacophores have been synthesized. We probed the effect of the linker on antibiotic activity with a series of selected synthetic analogues with varied length and substituents. A number of compounds demonstrated in vitro activity against several bacterial strains and showed activity against drug resistant strains of Pseudomonas aeruginosa. Among the compounds prepared, analogues 12a-d were novel 4,6-linked AMGs containing the nebramine pharmacophore. In addition the lead compound OPT-11 possessed an ED50 of <= 5 mg/kg in a Staphylococcus aureus ATCC 29213 mouse protection model. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.029

文献信息

• Structure–activity relationships of bivalent aminoglycosides and evaluation of their microbiological activities
  作者：Chang-Hsing Liang、Alex Romero、David Rabuka、Paulo W.M. Sgarbi、Kenneth A. Marby、Jonathan Duffield、Sulan Yao、Mayling L. Cheng、Yoshi Ichikawa、Pamela Sears、Changyong Hu、San-Bao Hwang、Youe-Kong Shue、Steven J. Sucheck

  DOI：10.1016/j.bmcl.2005.02.029

  日期：2005.4

  A library of 4,5- and 4,6-linked bivalent aminoglycoside (AMG) antibiotics consisting of neamine and nebramine pharmacophores have been synthesized. We probed the effect of the linker on antibiotic activity with a series of selected synthetic analogues with varied length and substituents. A number of compounds demonstrated in vitro activity against several bacterial strains and showed activity against drug resistant strains of Pseudomonas aeruginosa. Among the compounds prepared, analogues 12a-d were novel 4,6-linked AMGs containing the nebramine pharmacophore. In addition the lead compound OPT-11 possessed an ED50 of <= 5 mg/kg in a Staphylococcus aureus ATCC 29213 mouse protection model. (c) 2005 Elsevier Ltd. All rights reserved.