2,8-二(三氟甲基)-4-喹啉胺 | 917561-99-0

• 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: 2,8-二(三氟甲基)-4-喹啉胺
• 英文名称: 2,8-bis-(trifluoromethyl)-4-quinolinamine
• 英文别名: 2,8-bis(trifluoromethyl)quinolin-4-amine；4-Amino-2,8-bis(trifluoromethyl)-quinoline
• CAS: 917561-99-0
• 化学式: C₁₁H₆F₆N₂
• 分子量: 280.172
• InChiKey: JIVITABMOYYSAY-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：
  38.9
• 氢给体数：
  1
• 氢受体数：
  8

安全信息

• 危险品标志：
  Xi
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  2,8-二(三氟甲基)-4-喹啉胺 在 lithium hydroxide monohydrate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 0.5h， 生成 5-[[[N-2,8-bis(trifluoromethyl)-4-quinolinyl]amino]methyl]-3-isoxazolecarboxylic acid
  参考文献：
  名称：

  结核病的NOC化学-抗结核异恶唑-3-羧酸酯衍生物的结构-活性关系的进一步研究

  摘要：

  NOC，NOC！谁在那？通过设计和合成5-芳基和5-[（N-芳基）氨基]甲基类似物，我们扩展了3-异恶唑羧酸乙酯的结构-活性关系（SAR）。亚微摩尔浓度的化合物具有抗结核分枝杆菌（Mtb）的活性，对于某些化合物，在Vero细胞上未观察到毒性。

  DOI：

  10.1002/cmdc.201000169

文献信息

• From Serendipity to Rational Antituberculosis Drug Discovery of Mefloquine-Isoxazole Carboxylic Acid Esters
  作者：Jialin Mao、Hai Yuan、Yuehong Wang、Baojie Wan、Marco Pieroni、Qingqing Huang、Richard B. van Breemen、Alan P. Kozikowski、Scott G. Franzblau

  DOI：10.1021/jm900340a

  日期：2009.11.26

  Both in vitro and in vivo metabolism studies suggested that 5-(2,8-bis(trifluoromethyl)quinolin-4-yloxymethyl)isoxazole-3-carboxylic acid ethyl ester (compound 3) with previously reported anti-tuberculosis activity is rapidly converted to two metabolites 3a and 3b. In order to improve the metabolic stability of this series, chemistry efforts were focused on the modification of the oxymethylene linker of compound 3 in the present study. Compound 9d with an alkene linker was found to be both more metabolically stable and more potent than compound 3, with a minimum inhibitory concentration (MIC) of 0.2 mu M and 2.6 mu M against replicating and nonreplicating Mycobaterium tuberculosis, respectively. These attributes make 9d ail interesting lead compound. A number of modifications were made to the structure of 9d, and it series of active Compounds were discovered. Although some neurotoxicity was observed at it high dosage, this new series was endowed with both improved in vitro anti-TB activity and metabolic stability in comparison to compound 3.
• NOC Chemistry for Tuberculosis-Further Investigations on the Structure-Activity Relationships of Antitubercular Isoxazole-3-carboxylic Acid Ester Derivatives
  作者：Marco Pieroni、Annamaria Lilienkampf、Yuehong Wang、Baojie Wan、Sanghyun Cho、Scott G. Franzblau、Alan P. Kozikowski

  DOI：10.1002/cmdc.201000169

  日期：——

  NOC, NOC! Who's there? We have expanded the body of structure–activity relationships (SAR) regarding the 3‐isoxazolecarboxylic acid ethyl esters by the design and synthesis of 5‐aryl‐ and 5‐[(N‐aryl)amino]methyl analogues. Compounds were active against Mycobacterium tuberculosis (Mtb) at sub‐micromolar concentrations and, for selected compounds, no toxicity was observed on Vero cells.

  NOC，NOC！谁在那？通过设计和合成5-芳基和5-[（N-芳基）氨基]甲基类似物，我们扩展了3-异恶唑羧酸乙酯的结构-活性关系（SAR）。亚微摩尔浓度的化合物具有抗结核分枝杆菌（Mtb）的活性，对于某些化合物，在Vero细胞上未观察到毒性。