4-hydrazinyl-2,8-bis(trifluoromethyl)quinoline | 1236921-61-1

• 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
• 英文名称: 4-hydrazinyl-2,8-bis(trifluoromethyl)quinoline
• 英文别名: [2,8-Bis(trifluoromethyl)quinolin-4-yl]hydrazine
• CAS: 1236921-61-1
• 化学式: C₁₁H₇F₆N₃
• 分子量: 295.187
• InChiKey: DXVNHHHHAJBWQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  50.9
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3-二氢苯并呋喃-5-甲醛 、 4-hydrazinyl-2,8-bis(trifluoromethyl)quinoline 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 以73%的产率得到(E)-1-(2,8-bis(trifluoromethyl)quinolin-4-yl)-2-((2,3-dihydrobenzofuran-5-yl)methylene)hydrazine
  参考文献：
  名称：

  New quinoline derivatives: Synthesis and investigation of antibacterial and antituberculosis properties

  摘要：

  Four new series of quinoline derivatives were synthesized starting from 2-trifluoromethyl aniline through multi-step reactions. In the reaction sequence, substituted aniline was cyclized to 4-hydroxy quinoline 1, which was then transformed to 4-chloro-2,8-bis(trifluoromethyl)quinoline 2. The key scaffold 4-hydrazinyl-2,8-bis(trifluoromethyl)quinoline 3, obtained from the compound 2, was successfully converted to target quinoline derivatives, viz. hydrazones 4a-t, ureas 5a-e, thioureas 6a-c and pyrazoles 7a-d, in good yields. The newly synthesized title compounds were evaluated for their in vitro antibacterial activity against Escherichia coli. Staphylococcus aureus, Pseudomonas aeruginosa and Klebsiella pneumoniae (recultured) and antituberculosis activity against Mycobacterium tuberculosis H(37)Rv and MDR-TB. Preliminary results indicated that most of the hydrazone derivatives demonstrated very good antibacterial and antituberculosis activities while other derivatives showed moderate activity. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.04.022
• 作为产物：
  描述：

  2,8-双(三氟甲基)-4-羟基喹啉 在 三乙胺 、 肼 、 三氯化磷 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 4-hydrazinyl-2,8-bis(trifluoromethyl)quinoline
  参考文献：
  名称：

  天然奎宁生物碱启发的新型喹啉衍生物的设计，合成和抗真菌评价

  摘要：

  受奎宁及其类似物的启发，我们设计，合成和评估了两个系列的喹啉小分子化合物（a和2a）和六个系列的喹啉衍生物（3a - f）的抗真菌活性。结果表明，化合物3e和3f系列表现出显着的杀真菌活性。值得注意的是，化合物3f-4（EC 50 = 0.41μg/ mL）和3f-28（EC 50 = 0.55μg/ mL）显示出优异的体外杀真菌活性和对菌核菌的有效体内治疗作用。初步机理研究表明，化合物3f-4和3f-28可能引起细胞膜通透性改变，活性氧的积累，线粒体膜电位的丧失以及有效抑制菌核菌的发芽和形成。这些结果表明，化合物3f-4和3f-28是对抗源自天然产物的核盘菌的新型潜在杀真菌剂。

  DOI：

  10.1021/acs.jafc.9b04224

文献信息

• HETEROARYL SUBSTITUTED PYRIDAZINONE DERIVATIVES
  申请人：Alberati Daniela

  公开号：US20100216793A1

  公开（公告）日：2010-08-26

  The present invention is concerned with novel pyridazinone derivatives of formula (I) wherein R 1 , R 2 , R 3 and R 4 are as defined in the description and in the claims, as well as physiologically acceptable salts and esters thereof. These compounds inhibit PDE10A and can be used as pharmaceuticals.

  本发明涉及具有如下式（I）的新型吡啶并嗪酮衍生物，其中R1、R2、R3和R4如描述和索赔中所定义，并且其生理上可接受的盐和酯。这些化合物抑制PDE10A并可用作药物。
• US9187455B2
  申请人：——

  公开号：US9187455B2

  公开（公告）日：2015-11-17
• [EN] HETEROARYL SUBSTITUTED PYRIDAZINONE DERIVATIVES<br/>[FR] DÉRIVÉS DE PYRIDAZONE À SUBSTITUTION HÉTÉROARYLE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2010094762A1

  公开（公告）日：2010-08-26

  The present invention is concerned with novel pyridazinone derivatives of formula (I) wherein R1, R2, R3 and R4 are as defined in the description and in the claims, as well as physiologically acceptable salts and esters thereof. These compounds inhibit PDE10A and can be used as medicaments.
• New quinoline derivatives: Synthesis and investigation of antibacterial and antituberculosis properties
  作者：Sumesh Eswaran、Airody Vasudeva Adhikari、Imran H. Chowdhury、Nishith K. Pal、K.D. Thomas

  DOI：10.1016/j.ejmech.2010.04.022

  日期：2010.8

  Four new series of quinoline derivatives were synthesized starting from 2-trifluoromethyl aniline through multi-step reactions. In the reaction sequence, substituted aniline was cyclized to 4-hydroxy quinoline 1, which was then transformed to 4-chloro-2,8-bis(trifluoromethyl)quinoline 2. The key scaffold 4-hydrazinyl-2,8-bis(trifluoromethyl)quinoline 3, obtained from the compound 2, was successfully converted to target quinoline derivatives, viz. hydrazones 4a-t, ureas 5a-e, thioureas 6a-c and pyrazoles 7a-d, in good yields. The newly synthesized title compounds were evaluated for their in vitro antibacterial activity against Escherichia coli. Staphylococcus aureus, Pseudomonas aeruginosa and Klebsiella pneumoniae (recultured) and antituberculosis activity against Mycobacterium tuberculosis H(37)Rv and MDR-TB. Preliminary results indicated that most of the hydrazone derivatives demonstrated very good antibacterial and antituberculosis activities while other derivatives showed moderate activity. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Design, Synthesis, and Antifungal Evaluation of Novel Quinoline Derivatives Inspired from Natural Quinine Alkaloids
  作者：Guan-Zhou Yang、Jia-Kai Zhu、Xiao-Dan Yin、Yin-Fang Yan、Yu-Ling Wang、Xiao-Fei Shang、Ying-Qian Liu、Zhong-Min Zhao、Jing-Wen Peng、Hua Liu

  DOI：10.1021/acs.jafc.9b04224

  日期：2019.10.16

  Inspired by quinine and its analogues, we designed, synthesized, and evaluated two series of quinoline small molecular compounds (a and 2a) and six series of quinoline derivatives (3a–f) for their antifungal activities. The results showed that compounds 3e and 3f series exhibited significant fungicidal activities. Significantly, compounds 3f-4 (EC50 = 0.41 μg/mL) and 3f-28 (EC50 = 0.55 μg/mL) displayed

  受奎宁及其类似物的启发，我们设计，合成和评估了两个系列的喹啉小分子化合物（a和2a）和六个系列的喹啉衍生物（3a - f）的抗真菌活性。结果表明，化合物3e和3f系列表现出显着的杀真菌活性。值得注意的是，化合物3f-4（EC 50 = 0.41μg/ mL）和3f-28（EC 50 = 0.55μg/ mL）显示出优异的体外杀真菌活性和对菌核菌的有效体内治疗作用。初步机理研究表明，化合物3f-4和3f-28可能引起细胞膜通透性改变，活性氧的积累，线粒体膜电位的丧失以及有效抑制菌核菌的发芽和形成。这些结果表明，化合物3f-4和3f-28是对抗源自天然产物的核盘菌的新型潜在杀真菌剂。