4'',6''-O-cyclohexylidene-3,2',6',3'',4'''-pentakis(N-tert-butoxucarbonyl)arbekacin | 189157-32-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4'',6''-O-cyclohexylidene-3,2',6',3'',4'''-pentakis(N-tert-butoxucarbonyl)arbekacin
• CAS: 189157-32-2
• 化学式: C₅₃H₉₂N₆O₂₀
• 分子量: 1133.34
• InChiKey: BVPNHFVISZXSDN-VQAZRFGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  79.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  336.82
• 氢给体数：
  9.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 4'',6''-O-cyclohexylidene-3,2',6',3'',4'''-pentakis(N-tert-butoxucarbonyl)arbekacin 在 吡啶 作用下， 反应 3.33h， 生成 2'',2'''-di-O-benzoyl-4'',6''-O-cyclohexylidene-3,2',6',3'',4'''-pentakis(N-tert-butoxucarbonyl)arbekacin
  参考文献：
  名称：

  EP1710248

  摘要：

  公开号：
• 作为产物：
  描述：

  环己酮二甲缩酮 、 3,2',6',3'',4'''-pentakis(N-tert-butoxucarbonyl)arbekacin 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 50.0 ℃ 、4.0 kPa 条件下， 反应 2.0h， 生成 4'',6''-O-cyclohexylidene-3,2',6',3'',4'''-pentakis(N-tert-butoxucarbonyl)arbekacin
  参考文献：
  名称：

  Synthesis of 2″-oxidized derivatives of 5-deoxy-5-epi-5-fluoro-dibekacin and -arbekacin, and study on structure-chemical shift relationships of urethane(or amide)-type NH protons in synthetic intermediates

  摘要：

  Three 2''-modified dibekacin-analogs have been prepared as potential compounds active against resistant bacteria producing 2''-O-phosphotransferases; one is 5-deoxy-5,2''-diepi-5-fluorodibekacin (9) prepared from a suitably protected 2''-O-triflyl derivative through the 2'',3''-cyclic carbamate, and the others are 2''-oxo derivatives (12 and 22, both as the hydrate) of 5-deoxy-5-epi-5-fluoro-dibekacin and -arbekacin prepared through oxidation at C-2'' of suitably protected derivatives. Relationships between the t-butoxycarbonyl(= Boc)-NH-shifts of per-N-Boc synthetic intermediates and their structures were studied. It was found that the shifts, measured in pyridine-d(5) at 80 degrees C, which spread over a close range (delta 6-7 ppm), are sensitively influenced by nearby and surrounding groups around the BocNH group in respect of electron-withdrawing character, hydrogen bonding (BocNH ... acceptor), and also solvent effects (BocNH ... NC5H5). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00318-7

文献信息

• Effect of varying the 4″-position of arbekacin derivatives on antibacterial activity against MRSA and Pseudomonas aeruginosa
  作者：Yukiko Hiraiwa、Nobuto Minowa、Takayuki Usui、Yoshihisa Akiyama、Kazunori Maebashi、Daishiro Ikeda

  DOI：10.1016/j.bmcl.2007.08.059

  日期：2007.11

  4 ''-Deoxy-4 ''-episubstituted arbekacin derivatives and 4 ''-epi-5-deoxy-5-episubstituted arbekacin derivatives were designed and synthesized. Arbekacin and 4 ''-epiarbekacin both displayed the same antibacterial activity against Staphylococcus aureus (including methicillin-resistant S. aureus (MRSA)) and Pseudomonas aeruginosa. The 4 ''-epi-5-deoxy-5-episubstituted arbekacin derivatives showed potent antibacterial activity. Among them, the antibacterial activity of 5,4 ''-diepiarbekacin was superior to that of arbekacin or 5-episubstituted arbekacin against Gram-positive and Gram-negative bacteria. The 6 '-N-methyl derivative of the 5,4 ''-diepiarbekacin was effective against P. aeruginosa expressing an aminoglycoside-modifying enzyme AAC(6 ')-Ib. (C) 2007 Elsevier Ltd. All rights reserved.