4-(2-Chlorophenyl)sulfanyl-2-(trichloromethyl)quinazoline | 1336933-33-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-(2-Chlorophenyl)sulfanyl-2-(trichloromethyl)quinazoline
• CAS: 1336933-33-5
• 化学式: C₁₅H₈Cl₄N₂S
• 分子量: 390.12
• InChiKey: SEVPSZYHMSRSCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻氯苯硫酚 、 4-氯-2-三氯甲基喹唑啉 在 sodium hydride 作用下， 以 二甲基亚砜 、 mineral oil 为溶剂， 反应 1.33h， 以75%的产率得到4-(2-Chlorophenyl)sulfanyl-2-(trichloromethyl)quinazoline
  参考文献：
  名称：

  4-Thiophenoxy-2-trichloromethyquinazolines display in vitro selective antiplasmodial activity against the human malaria parasite Plasmodium falciparum

  摘要：

  A series of original quinazolines bearing a 4-thiophenoxy and a 2-trichloromethyl group was synthesized in a convenient and efficient way and was evaluated toward its in vitro antiplasmodial potential. The series revealed global good activity against the K1-multi-resistant Plasmodium falciparum strain, especially with hit compound 5 (IC50 = 0.9 mu M), in comparison with chloroquine and doxycycline chosen as reference-drugs. Both the in vitro cytotoxicity study which was conducted on the human HepG2 cell line and the in vitro antitoxoplasmic screening against Toxoplasma gondii indicate that this series presents an interesting selective antiplasmodial profile. Structure-activity- and toxicity relationships highlight that the trichloromethyl group plays a key role in the antiplasmodial activity and also show that the modulation of the thiophenol moiety influences the toxicity/activity ratio. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.113

文献信息

• 4-Thiophenoxy-2-trichloromethyquinazolines display in vitro selective antiplasmodial activity against the human malaria parasite Plasmodium falciparum
  作者：Pierre Verhaeghe、Aurélien Dumètre、Caroline Castera-Ducros、Sébastien Hutter、Michèle Laget、Cyril Fersing、Marion Prieri、Julien Yzombard、France Sifredi、Sylvain Rault、Pascal Rathelot、Patrice Vanelle、Nadine Azas

  DOI：10.1016/j.bmcl.2011.06.113

  日期：2011.10

  A series of original quinazolines bearing a 4-thiophenoxy and a 2-trichloromethyl group was synthesized in a convenient and efficient way and was evaluated toward its in vitro antiplasmodial potential. The series revealed global good activity against the K1-multi-resistant Plasmodium falciparum strain, especially with hit compound 5 (IC50 = 0.9 mu M), in comparison with chloroquine and doxycycline chosen as reference-drugs. Both the in vitro cytotoxicity study which was conducted on the human HepG2 cell line and the in vitro antitoxoplasmic screening against Toxoplasma gondii indicate that this series presents an interesting selective antiplasmodial profile. Structure-activity- and toxicity relationships highlight that the trichloromethyl group plays a key role in the antiplasmodial activity and also show that the modulation of the thiophenol moiety influences the toxicity/activity ratio. (C) 2011 Elsevier Ltd. All rights reserved.