(2R,3R,4S,5R)-2-(6-amino-2-(((1r,4R)-4-methylcyclohexyl)oxy)-9H-purin-9-yl)-5-methyltetrahydrofuran-3,4-diol | 883729-10-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: (2R,3R,4S,5R)-2-(6-amino-2-(((1r,4R)-4-methylcyclohexyl)oxy)-9H-purin-9-yl)-5-methyltetrahydrofuran-3,4-diol
• CAS: 883729-10-0
• 化学式: C₁₇H₂₅N₅O₄
• 分子量: 363.417
• InChiKey: BPKWHAUDIQIJCD-XULTWRPTSA-N

物化性质

• 沸点：
  658.0±65.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.01
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  128.54
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  2-氯腺嘌呤核苷 在 吡啶 、 水 、 三乙基硼氢化锂 、 对甲苯磺酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 生成 (2R,3R,4S,5R)-2-(6-amino-2-(((1r,4R)-4-methylcyclohexyl)oxy)-9H-purin-9-yl)-5-methyltetrahydrofuran-3,4-diol
  参考文献：
  名称：

  Discovery of bacterial NAD+-dependent DNA ligase inhibitors: Improvements in clearance of adenosine series

  摘要：

  Optimization of clearance of adenosine inhibitors of bacterial NAD(+)-dependent DNA ligase is discussed. To reduce Cytochrome P-450-mediated metabolic clearance, many strategies were explored; however, most modifications resulted in compounds with reduced antibacterial activity and/or unchanged total clearance. The alkyl side chains of the 2-cycloalkoxyadenosines were fluorinated, and compounds with moderate antibacterial activity and favorable pharmacokinetic properties in rat and dog were identified. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.071

文献信息

• SUBSTITUTED ADENINES AND THE USES THEREOF
  申请人：Cavero-Tomas Marta

  公开号：US20090048203A1

  公开（公告）日：2009-02-19

  This invention relates to compounds of Formula (I): and their use in the treatment of bacterial infections.

  本发明涉及式(I)的化合物及其在治疗细菌感染方面的应用。
• Discovery of bacterial NAD+-dependent DNA ligase inhibitors: Improvements in clearance of adenosine series
  作者：Suzanne S. Stokes、Madhusudhan Gowravaram、Hoan Huynh、Min Lu、George B. Mullen、Brendan Chen、Robert Albert、Thomas J. O’Shea、Michael T. Rooney、Haiqing Hu、Joseph V. Newman、Scott D. Mills

  DOI：10.1016/j.bmcl.2011.11.071

  日期：2012.1

  Optimization of clearance of adenosine inhibitors of bacterial NAD(+)-dependent DNA ligase is discussed. To reduce Cytochrome P-450-mediated metabolic clearance, many strategies were explored; however, most modifications resulted in compounds with reduced antibacterial activity and/or unchanged total clearance. The alkyl side chains of the 2-cycloalkoxyadenosines were fluorinated, and compounds with moderate antibacterial activity and favorable pharmacokinetic properties in rat and dog were identified. (C) 2011 Elsevier Ltd. All rights reserved.