| 1588776-73-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• CAS: 1588776-73-1
• 化学式: C₂₂H₂₇NO₂
• 分子量: 337.462
• InChiKey: QGCSDJQPXNOVHF-NBVRZTHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.03
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  在 lithium aluminium tetrahydride 、 ammonium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 10.33h， 以60%的产率得到(E)-3,7-dimethyl-N-(2-(naphthalen-1-yloxy)ethyl)octa-2,6-dien-1-amine
  参考文献：
  名称：

  Multitarget Drug Discovery for Tuberculosis and Other Infectious Diseases

  摘要：

  We report the discovery of a series of new drug leads that have potent activity against Mycobacterium tuberculosis as well as against other bacteria, fungi, and a malaria parasite. The compounds are analogues of the new tuberculosis (TB) drug SQ109 (1), which has been reported to act by inhibiting a transporter called MmpL3, involved in cell wall biosynthesis. We show that 1 and the new compounds also target enzymes involved in menaquinone biosynthesis and electron transport, inhibiting respiration and ATP biosynthesis, and are uncouplers, collapsing the pH gradient and membrane potential used to power transporters. The result of such multitarget inhibition is potent inhibition of TB cell growth, as well as very low rates of spontaneous drug resistance. Several targets are absent in humans but are present in other bacteria, as well as in malaria parasites, whose growth is also inhibited.

  DOI：

  10.1021/jm500131s
• 作为产物：
  描述：

  香叶胺 在 四丁基硫酸氢铵 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 氯仿 、 水 为溶剂， 反应 16.5h， 生成
  参考文献：
  名称：

  Multitarget Drug Discovery for Tuberculosis and Other Infectious Diseases

  摘要：

  We report the discovery of a series of new drug leads that have potent activity against Mycobacterium tuberculosis as well as against other bacteria, fungi, and a malaria parasite. The compounds are analogues of the new tuberculosis (TB) drug SQ109 (1), which has been reported to act by inhibiting a transporter called MmpL3, involved in cell wall biosynthesis. We show that 1 and the new compounds also target enzymes involved in menaquinone biosynthesis and electron transport, inhibiting respiration and ATP biosynthesis, and are uncouplers, collapsing the pH gradient and membrane potential used to power transporters. The result of such multitarget inhibition is potent inhibition of TB cell growth, as well as very low rates of spontaneous drug resistance. Several targets are absent in humans but are present in other bacteria, as well as in malaria parasites, whose growth is also inhibited.

  DOI：

  10.1021/jm500131s