8-(5-benzyloxy-1H-indol-1-yl)-1-octyl methanesulfonate | 578726-14-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 8-(5-benzyloxy-1H-indol-1-yl)-1-octyl methanesulfonate
• 英文别名: 8-(5-Phenylmethoxyindol-1-yl)octyl methanesulfonate
• CAS: 578726-14-4
• 化学式: C₂₄H₃₁NO₄S
• 分子量: 429.58
• InChiKey: QOGLAPCWOWWAJA-UHFFFAOYSA-N

物化性质

• 沸点：
  621.6±40.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  65.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-(5-benzyloxy-1H-indol-1-yl)-1-octyl methanesulfonate 在 potassium carbonate 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 {3-[8-(5-Benzyloxy-indol-1-yl)-octyloxycarbonyl]-phenyl}-trimethyl-ammonium; iodide
  参考文献：
  名称：

  Tethered Dimers as NAD Synthetase Inhibitors with Antibacterial Activity

  摘要：

  The solution-phase parallel synthesis of tethered dimers was employed to identify lead inhibitors of bacterial NAD synthetase. Active dimers contained two aromatic end groups joined by a polymethylene linker, with one end group containing a permanent positive charge. Effective inhibitors of NAD synthetase also inhibited the growth of Gram-positive (but not Gram-negative) bacteria, including antibiotic-resistant strains. The desmethyl precursors of active inhibitors lacked a permanent positive charge and were inactive as either enzyme inhibitors or antibacterial agents. Similarly, a close structural analogue of the most active inhibitors contained two additional ether oxygens in the tether and was inactive in both assays. These results are consistent with the premise that NAD synthetase inhibition is responsible for the antibacterial actions and support further studies on NAD synthetase as a new target for antibacterial agents.

  DOI：

  10.1021/jm030003x
• 作为产物：
  描述：

  5-苄氧基吲哚 在 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 8-(5-benzyloxy-1H-indol-1-yl)-1-octyl methanesulfonate
  参考文献：
  名称：

  Tethered Dimers as NAD Synthetase Inhibitors with Antibacterial Activity

  摘要：

  The solution-phase parallel synthesis of tethered dimers was employed to identify lead inhibitors of bacterial NAD synthetase. Active dimers contained two aromatic end groups joined by a polymethylene linker, with one end group containing a permanent positive charge. Effective inhibitors of NAD synthetase also inhibited the growth of Gram-positive (but not Gram-negative) bacteria, including antibiotic-resistant strains. The desmethyl precursors of active inhibitors lacked a permanent positive charge and were inactive as either enzyme inhibitors or antibacterial agents. Similarly, a close structural analogue of the most active inhibitors contained two additional ether oxygens in the tether and was inactive in both assays. These results are consistent with the premise that NAD synthetase inhibition is responsible for the antibacterial actions and support further studies on NAD synthetase as a new target for antibacterial agents.

  DOI：

  10.1021/jm030003x

文献信息

• Tethered Dimers as NAD Synthetase Inhibitors with Antibacterial Activity
  作者：Sadanandan E. Velu、Walter A. Cristofoli、Gabriel J. Garcia、Christie G. Brouillette、Milton C. Pierson、Chi-Hao Luan、Lawrence J. DeLucas、Wayne J. Brouillette

  DOI：10.1021/jm030003x

  日期：2003.7.1

  The solution-phase parallel synthesis of tethered dimers was employed to identify lead inhibitors of bacterial NAD synthetase. Active dimers contained two aromatic end groups joined by a polymethylene linker, with one end group containing a permanent positive charge. Effective inhibitors of NAD synthetase also inhibited the growth of Gram-positive (but not Gram-negative) bacteria, including antibiotic-resistant strains. The desmethyl precursors of active inhibitors lacked a permanent positive charge and were inactive as either enzyme inhibitors or antibacterial agents. Similarly, a close structural analogue of the most active inhibitors contained two additional ether oxygens in the tether and was inactive in both assays. These results are consistent with the premise that NAD synthetase inhibition is responsible for the antibacterial actions and support further studies on NAD synthetase as a new target for antibacterial agents.