2-三氯甲基喹啉 | 4032-53-5

• 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: 2-三氯甲基喹啉
• 英文名称: 2-trichloromethylquinoline
• 英文别名: 2-trichloromethyl-quinoline；2-Trichlormethyl-chinolin；Trichlor-chinaldin；Trichlorchinaldin；2-(Trichloromethyl)quinoline
• CAS: 4032-53-5
• 化学式: C₁₀H₆Cl₃N
• 分子量: 246.523
• InChiKey: KASSNQGPPUVYNL-UHFFFAOYSA-N

物化性质

• 熔点：
  56 °C
• 沸点：
  325.9±37.0 °C(Predicted)
• 密度：
  1.466±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  2-三氯甲基喹啉 在 盐酸 、 tin 、 溶剂黄146 作用下， 生成 2-(氯甲基)喹啉
  参考文献：
  名称：

  Brown et al., Journal of the Chemical Society, 1951, p. 1145,1147

  摘要：

  DOI：
• 作为产物：
  描述：

  2-甲基喹啉 在 sodium acetate 、 氯 、 溶剂黄146 作用下， 生成 2-三氯甲基喹啉
  参考文献：
  名称：

  Hammick, Journal of the Chemical Society, 1923, vol. 123, p. 2883

  摘要：

  DOI：

文献信息

• Folli, Ugo; Goldoni, Francesca; Iarossi, Dario, Journal of the Chemical Society. Perkin transactions II, 1995, # 5, p. 1017 - 1020
  作者：Folli, Ugo、Goldoni, Francesca、Iarossi, Dario、Sbardellati, Silvia、Taddei, Ferdinando

  DOI：——

  日期：——
• Discovery of a new antileishmanial hit in 8-nitroquinoline series
  作者：Lucie Paloque、Pierre Verhaeghe、Magali Casanova、Caroline Castera-Ducros、Aurélien Dumètre、Litaty Mbatchi、Sébastien Hutter、Manel Kraiem-M'Rabet、Michèle Laget、Vincent Remusat、Sylvain Rault、Pascal Rathelot、Nadine Azas、Patrice Vanelle

  DOI：10.1016/j.ejmech.2012.04.029

  日期：2012.8

  A series of nitrated 2-substituted-quinolines was synthesized and evaluated in vitro toward Leishmania donovani promastigotes. In parallel, the in vitro cytotoxicity of these molecules was assessed on the murine J774 and human HepG2 cell lines. Thus, a very promising antileishmanial hit molecule was identified (compound 21), displaying an IC50 value of 6.6 mu M and CC50 values >= 100 mu M, conferring quite good selectivity index to this molecule, in comparison with 3 drug-compounds of reference (amphotericin B, miltefosine and pentamidine). Compound 21 also appears as an efficient in vitro antileishmanial molecule against both Leishmania infantum promastigotes and the intracellular L. donovani amastigotes (respective IC50 = 7.6 and 6.5 mu M). Moreover, hit quinoline 21 does not show neither significant antiplasmodial nor antitoxoplasmic in vitro activity and though, presents a selective antileishmanial activity. Finally, a structure activity relationships study enabled to define precisely the antileishmanial pharmacophore based on this nitroquinoline scaffold: 2-hydroxy-8-nitroquinoline. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Hammick et al., Journal of the Chemical Society, 1955, p. 2436,2440
  作者：Hammick et al.

  DOI：——

  日期：——
• Synthesis and in vitro evaluation of 4-trichloromethylpyrrolo[1,2-a]quinoxalines as new antiplasmodial agents
  作者：Nicolas Primas、Peggy Suzanne、Pierre Verhaeghe、Sébastien Hutter、Charline Kieffer、Michèle Laget、Anita Cohen、Julie Broggi、Jean-Charles Lancelot、Aurélien Lesnard、Patrick Dallemagne、Pascal Rathelot、Sylvain Rault、Patrice Vanelle、Nadine Azas

  DOI：10.1016/j.ejmech.2014.06.014

  日期：2014.8

  Thanks to a preliminary in vitro screening of several CCl3-substituted-nitrogen containing heterocycles belonging to our chemical library, the 2-trichloromethylquinoxaline scaffold appeared to be of potential interest for developing new antiplasmodial agents. Then, combining these experimental results to the antimalarial properties reported for various pyrrolo[1,2-a]quinoxaline derivatives, an original series of fifteen 7-substituted-4-trichoromethylpyrrolo[1,2-a]quinoxalines was synthesized in a 4 to 5 reaction steps pathway. All molecules were evaluated in vitro toward both their antiplasmodial activity on the K1 multi-resistant Plasmodium falciparum strain and their cytotoxicity on the HepG2 human cell line. Thus, 3 hit molecules were identified, displaying IC50 values in the micromolar range and low cytotoxicity values, reaching good selectivity indexes, in comparison with the reference drugs chloroquine and doxycycline. Structure-activity relationship studies showed that the pyrrolo[1,2-a]quinoxaline scaffold can support selective antiplasmodial activity when substituted at position 4 by a CCl3 group. However, substitution at position 7 of the same scaffold is neither beneficial for cytotoxicity nor favourable for the solubility in the biological media.
• Kato, Tetsuzo; Katagiri, Nobuya; Wagai, Akihiro, Chemical and pharmaceutical bulletin, 1981, vol. 29, # 4, p. 1069 - 1075
  作者：Kato, Tetsuzo、Katagiri, Nobuya、Wagai, Akihiro

  DOI：——

  日期：——