4-(trichloromethyl)quinazoline | 99356-81-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-(trichloromethyl)quinazoline
• CAS: 99356-81-7
• 化学式: C₉H₅Cl₃N₂
• 分子量: 247.511
• InChiKey: LCLJJOZPSXRCIX-UHFFFAOYSA-N

物化性质

• 熔点：
  91-91.5 °C(Solv: ligroine (8032-32-4))
• 沸点：
  348.9±37.0 °C(Predicted)
• 密度：
  1.534±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(trichloromethyl)quinazoline 生成 4-methoxy-4-(trichloromethyl)-1H-quinazoline
  参考文献：
  名称：

  MENCARELLI, P.;STEGEL, F., J. ORG. CHEM., 1985, 50, N 25, 5415-5417

  摘要：

  DOI：
• 作为产物：
  描述：

  (6CI,7CI,8CI,9CI)-4-甲基喹唑啉 在 sodium acetate 、 氯 作用下， 以 溶剂黄146 为溶剂， 以1.4 g的产率得到4-(trichloromethyl)quinazoline
  参考文献：
  名称：

  Formation of a neutral covalent adduct in the nucleophilic aromatic substitution reaction involving a carbon leaving group

  摘要：

  DOI：

  10.1021/jo00225a092

文献信息

• 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.
• Carbon leaving group in aromatic nucleophilic substitution. Quantitative comparison with a common leaving group
  作者：Mario Mattioli、Paolo Mencarelli、Franco Stegel

  DOI：10.1021/jo00240a030

  日期：1988.3
• Reactions of 4-(trihalomethyl)quinazolines with aliphatic amines. Role of the halogen atom and of the amine on the reaction pattern
  作者：Mario Mattioli、Paolo Mencarelli

  DOI：10.1021/jo00289a070

  日期：1990.1
• Formation of a neutral covalent adduct in the nucleophilic aromatic substitution reaction involving a carbon leaving group
  作者：Paolo Mencarelli、Franco Stegel

  DOI：10.1021/jo00225a092

  日期：1985.12
• MENCARELLI, P.;STEGEL, F., J. ORG. CHEM., 1985, 50, N 25, 5415-5417
  作者：MENCARELLI, P.、STEGEL, F.

  DOI：——

  日期：——