2,5-双三氟甲基-4-羟基喹啉 | 35853-44-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 2,5-双三氟甲基-4-羟基喹啉
• 英文名称: 2,5-Bis-(trifluormethyl)-4-chinolinol
• 英文别名: 2,5-bis(trifluoromethyl)-4-quinolinol；2,5-Bis(trifluoromethyl)quinolin-4-ol；2,5-bis(trifluoromethyl)-1H-quinolin-4-one
• CAS: 35853-44-2
• 化学式: C₁₁H₅F₆NO
• 分子量: 281.157
• InChiKey: DOCZCYFBVOIVFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,5-双三氟甲基-4-羟基喹啉 、 3-溴丙炔 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 2,5-bis(trifluoromethyl)-4-(2-propyn-1-yloxy)quinoline
  参考文献：
  名称：

  Structure−Activity Relationships for a Series of Quinoline-Based Compounds Active against Replicating and Nonreplicating Mycobacterium tuberculosis

  摘要：

  Tuberculosis (TB) remains as a global pandemic that is aggravated by a lack of health care, the spread of HIV, and the emergence of multidrug-resistant TB (MDR-TB) and extensively drug-resistant TB (XDR-TB) strains. New anti-TB drugs are urgently required to shorten the long 6-12 month treatment regimen and to battle drug-resistant Mtb strains. We have identified several potent quinoline-based anti-TB compounds, bearing an isoxazole containing side-chain. The most potent compounds, 7g and 13, exhibited submicromolar activity against the replicating bacteria (R-TB), with minimum inhibitory concentrations (MICs) of 0.77 and 0.95 mu M, respectively. In general, these compounds also had micromolar activity against the nonreplicating persistent bacteria (NRP-TB) and did not show toxicity on Vero cells up to 128 mu M concentration. Compounds 7g and 13 were shown to retain their anti-TB activity against rifampin, isoniazid, and streptomycin resistant Mtb strains. The results suggest that quinoline-isoxazole-based anti-TB compounds are promising leads for new TB drug development.

  DOI：

  10.1021/jm900003c
• 作为产物：
  描述：

  间氨基三氟甲苯 、 三氟乙酰乙酸乙酯 在 PPA 作用下， 生成 2,5-双三氟甲基-4-羟基喹啉 、 2,7-双三氟甲基-4-羟基喹啉
  参考文献：
  名称：

  Structure−Activity Relationships for a Series of Quinoline-Based Compounds Active against Replicating and Nonreplicating Mycobacterium tuberculosis

  摘要：

  Tuberculosis (TB) remains as a global pandemic that is aggravated by a lack of health care, the spread of HIV, and the emergence of multidrug-resistant TB (MDR-TB) and extensively drug-resistant TB (XDR-TB) strains. New anti-TB drugs are urgently required to shorten the long 6-12 month treatment regimen and to battle drug-resistant Mtb strains. We have identified several potent quinoline-based anti-TB compounds, bearing an isoxazole containing side-chain. The most potent compounds, 7g and 13, exhibited submicromolar activity against the replicating bacteria (R-TB), with minimum inhibitory concentrations (MICs) of 0.77 and 0.95 mu M, respectively. In general, these compounds also had micromolar activity against the nonreplicating persistent bacteria (NRP-TB) and did not show toxicity on Vero cells up to 128 mu M concentration. Compounds 7g and 13 were shown to retain their anti-TB activity against rifampin, isoniazid, and streptomycin resistant Mtb strains. The results suggest that quinoline-isoxazole-based anti-TB compounds are promising leads for new TB drug development.

  DOI：

  10.1021/jm900003c

文献信息

• Trifluoromethyl substituted analogs of quinine and quinidine
  申请人：Hoffmann-La Roche Inc.

  公开号：US03953453A1

  公开（公告）日：1976-04-27

  Trifluoromethyl substituted analogs of quinine and quinidine are prepared by reacting a 4-quinolyllithium compound with a 4,5-erythro-5-ethyl-(or vinyl)-quinuclidine-2 .xi.-carboxaldehyde or the corresponding quinuclidine-2 .xi.-carboxylic acid alkyl ester. The end products are useful as antimalarial agents.

  三氟甲基取代的奎宁和奎宁啶的类似物是通过将4-喹诺啉锂化合物与4,5-内消旋-5-乙基（或乙烯基）喹诺啉-2 .xi.-羧醛或相应的喹诺啉-2 .xi.-羧酸烷基酯反应制备的。最终产品可用作抗疟疾药物。
• US3953453A
  申请人：——

  公开号：US3953453A

  公开（公告）日：1976-04-27
• Structure−Activity Relationships for a Series of Quinoline-Based Compounds Active against Replicating and Nonreplicating <i>Mycobacterium tuberculosis</i>
  作者：Annamaria Lilienkampf、Jialin Mao、Baojie Wan、Yuehong Wang、Scott G. Franzblau、Alan P. Kozikowski

  DOI：10.1021/jm900003c

  日期：2009.4.9

  Tuberculosis (TB) remains as a global pandemic that is aggravated by a lack of health care, the spread of HIV, and the emergence of multidrug-resistant TB (MDR-TB) and extensively drug-resistant TB (XDR-TB) strains. New anti-TB drugs are urgently required to shorten the long 6-12 month treatment regimen and to battle drug-resistant Mtb strains. We have identified several potent quinoline-based anti-TB compounds, bearing an isoxazole containing side-chain. The most potent compounds, 7g and 13, exhibited submicromolar activity against the replicating bacteria (R-TB), with minimum inhibitory concentrations (MICs) of 0.77 and 0.95 mu M, respectively. In general, these compounds also had micromolar activity against the nonreplicating persistent bacteria (NRP-TB) and did not show toxicity on Vero cells up to 128 mu M concentration. Compounds 7g and 13 were shown to retain their anti-TB activity against rifampin, isoniazid, and streptomycin resistant Mtb strains. The results suggest that quinoline-isoxazole-based anti-TB compounds are promising leads for new TB drug development.