N-cycloheptyl-2-(trichloromethyl)quinazolin-4-amine | 1177248-54-2

• 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: N-cycloheptyl-2-(trichloromethyl)quinazolin-4-amine
• CAS: 1177248-54-2
• 化学式: C₁₆H₁₈Cl₃N₃
• 分子量: 358.698
• InChiKey: ROJDCXRGENVNCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  环庚胺 、 4-氯-2-三氯甲基喹唑啉 以78%的产率得到N-cycloheptyl-2-(trichloromethyl)quinazolin-4-amine
  参考文献：
  名称：

  Synthesis and in vitro antiplasmodial evaluation of 4-anilino-2-trichloromethylquinazolines

  摘要：

  To identify a new safe antiplasmodial molecular scaffold, an original series of 2-trichloromethylquinazolines, functionalized in position 4 by an alkyl-or arylamino substituent, was synthesized from 4-chloro-2-trichloromethylquinazoline 1, via a cheap, fast and efficient solvent-free operating procedure. Among the 40 molecules prepared, several exhibit a good profile with both a significant antiplasmodial activity on the W2 Plasmodium falciparum strain (IC50 values: 0.4-2.2 mu M) and a promising toxicological behavior regarding human cells (HepG2/W2 selectivity indexes: 40-83), compared to the antimalarial drug compounds chloroquine and doxycycline. The in vitro antitoxoplasmic and antileishmanial evaluations were conducted in parallel on the most active molecules, showing that these ones specifically display antiplasmodial properties. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.022

文献信息

• Synthesis and in vitro antiplasmodial evaluation of 4-anilino-2-trichloromethylquinazolines
  作者：Pierre Verhaeghe、Nadine Azas、Sébastien Hutter、Caroline Castera-Ducros、Michèle Laget、Aurélien Dumètre、Monique Gasquet、Jean-Pierre Reboul、Sylvain Rault、Pascal Rathelot、Patrice Vanelle

  DOI：10.1016/j.bmc.2009.05.022

  日期：2009.7

  To identify a new safe antiplasmodial molecular scaffold, an original series of 2-trichloromethylquinazolines, functionalized in position 4 by an alkyl-or arylamino substituent, was synthesized from 4-chloro-2-trichloromethylquinazoline 1, via a cheap, fast and efficient solvent-free operating procedure. Among the 40 molecules prepared, several exhibit a good profile with both a significant antiplasmodial activity on the W2 Plasmodium falciparum strain (IC50 values: 0.4-2.2 mu M) and a promising toxicological behavior regarding human cells (HepG2/W2 selectivity indexes: 40-83), compared to the antimalarial drug compounds chloroquine and doxycycline. The in vitro antitoxoplasmic and antileishmanial evaluations were conducted in parallel on the most active molecules, showing that these ones specifically display antiplasmodial properties. (C) 2009 Elsevier Ltd. All rights reserved.