3,6-Dimethoxy-2-naphthol | 33033-32-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3,6-Dimethoxy-2-naphthol
• 英文别名: 3,6-Dimethoxynaphthalen-2-ol
• CAS: 33033-32-8
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: YBDUNEJGOXEMMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,6-Dimethoxy-2-naphthol 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 5%-palladium/activated carbon 、 四丁基氟化铵 、 氢气 、 溶剂黄146 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 19.5h， 生成 2-aminoethanol;5-[2-(3,6-dimethoxynaphthalen-2-yl)ethyl]-2,4-dioxo-1H-pyrimidine-6-carboxylic acid
  参考文献：
  名称：

  Design and synthesis of potent substrate-based inhibitors of the Trypanosoma cruzi dihydroorotate dehydrogenase

  摘要：

  Chagas disease, caused by the parasitic protozoan Trypanosoma cruzi, is the leading cause of heart disease in Latin America. T. cruzi dihydroorotate dehydrogenase (DHODH), which catalyzes the production of orotate, was demonstrated to be essential for T. cruzi survival, and thus has been considered as a potential drug target to combat Chagas disease. Here we report the design and synthesis of 75 compounds based on the orotate structure. A comprehensive structure-activity relationship (SAR) study revealed two 5-substituted orotate analogues (5u and 5v) that exhibit nPP values of several ten nanomolar level and a selectivity of more than 30,000-fold over human DHODH. The information presented here will be invaluable in the search for next-generation drug leads for Chagas disease. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.01.009