tert-butyl ((3R,6S)-6-(iodomethyl)tetrahydro-2H-pyran-3-yl)carbamate | 881657-58-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: tert-butyl ((3R,6S)-6-(iodomethyl)tetrahydro-2H-pyran-3-yl)carbamate
• 英文别名: (3R,6S)-(6-iodomethyl-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester；tert-butyl N-[(3R,6S)-6-(iodomethyl)oxan-3-yl]carbamate
• CAS: 881657-58-5
• 化学式: C₁₁H₂₀INO₃
• 分子量: 341.189
• InChiKey: JFRDAJHOMKAWKJ-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl ((3R,6S)-6-(iodomethyl)tetrahydro-2H-pyran-3-yl)carbamate 在 hexaammonium heptamolybdate tetrahydrate 、 甲基磺酰胺 、 双氧水 、 双(三甲基硅烷基)氨基钾 、 三氟乙酸 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 、 水 、 乙酸乙酯 、 甲苯 、 叔丁醇 为溶剂， 反应 5.5h， 生成 (1S,2R)-1-[(2S,5R)-5-aminooxan-2-yl]-2-(6-methoxyquinolin-4-yl)ethane-1,2-diol
  参考文献：
  名称：

  Design, Synthesis, and Characterization of Novel Tetrahydropyran-Based Bacterial Topoisomerase Inhibitors with Potent Anti-Gram-Positive Activity

  摘要：

  There is an urgent need for new antibacterial drugs that are effective against infections caused by multidrug-resistant pathogens. Novel nonfluoroquinolone inhibitors of bacterial type II topoisomerases (DNA gyrase and topoisomerase IV) have the potential to become such drugs because they display potent antibacterial activity and exhibit no target-mediated cross-resistance with fluoroquinolones. Bacterial topoisomerase inhibitors that are built on a tetrahydropyran ring linked to a bicyclic aromatic moiety through a syn-diol linker show potent anti-Gram-positive activity, covering isolates with clinically relevant resistance phenotypes. For instance, analog 49c was found to be a dual DNA gyrase topoisomerase IV inhibitor, with broad antibacterial activity and low propensity for spontaneous resistance development, but suffered from high hERG K channel block. On the other hand, analog 49e displayed lower hERG K channel block while retaining potent in vitro antibacterial activity and acceptable frequency for resistance development. Furthermore, analog 49e showed moderate clearance in rat and promising in vivo efficacy against Staphylococcus aureus in a murine infection model.

  DOI：

  10.1021/jm400963y
• 作为产物：
  描述：

  ((2S,5R)-5-((tert-butoxycarbonyl)amino)tetrahydro-2H-pyran-2-yl)methyl 4-methylbenzenesulfonate 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以99%的产率得到tert-butyl ((3R,6S)-6-(iodomethyl)tetrahydro-2H-pyran-3-yl)carbamate
  参考文献：
  名称：

  Design, Synthesis, and Characterization of Novel Tetrahydropyran-Based Bacterial Topoisomerase Inhibitors with Potent Anti-Gram-Positive Activity

  摘要：

  There is an urgent need for new antibacterial drugs that are effective against infections caused by multidrug-resistant pathogens. Novel nonfluoroquinolone inhibitors of bacterial type II topoisomerases (DNA gyrase and topoisomerase IV) have the potential to become such drugs because they display potent antibacterial activity and exhibit no target-mediated cross-resistance with fluoroquinolones. Bacterial topoisomerase inhibitors that are built on a tetrahydropyran ring linked to a bicyclic aromatic moiety through a syn-diol linker show potent anti-Gram-positive activity, covering isolates with clinically relevant resistance phenotypes. For instance, analog 49c was found to be a dual DNA gyrase topoisomerase IV inhibitor, with broad antibacterial activity and low propensity for spontaneous resistance development, but suffered from high hERG K channel block. On the other hand, analog 49e displayed lower hERG K channel block while retaining potent in vitro antibacterial activity and acceptable frequency for resistance development. Furthermore, analog 49e showed moderate clearance in rat and promising in vivo efficacy against Staphylococcus aureus in a murine infection model.

  DOI：

  10.1021/jm400963y

文献信息

• 3-AMINO-6-(1-AMINO-ETHYL)-TETRAHYDROPYRAN DERIVATIVES
  申请人：Hubschwerlen Christian

  公开号：US20100179135A1

  公开（公告）日：2010-07-15

  Antibacterial compounds including 3-amino-6-(1-amino-ethyl)-tetrahydropyran derivatives are provided, and methods of treatment or prevention of bacterial infection with such compounds are provided.

  提供了包括3-氨基-6-(1-氨乙基)-四氢吡喃衍生物在内的抗菌化合物，并提供了使用这些化合物进行治疗或预防细菌感染的方法。
• WO2007/105154
  申请人：——

  公开号：——

  公开（公告）日：——
• WO2008/152603
  申请人：——

  公开号：——

  公开（公告）日：——
• NEW BICYCLIC ANTIBIOTICS
  申请人：Actelion Pharmaceuticals Ltd.

  公开号：EP1799676A2

  公开（公告）日：2007-06-27
• ANTIBIOTIC COMPOUNDS
  申请人：Actelion Pharmaceuticals Ltd.

  公开号：EP1996579A2

  公开（公告）日：2008-12-03