2-Bromo-4-(4-methylsulfanylphenyl)-1,3-thiazole | 1222968-56-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-Bromo-4-(4-methylsulfanylphenyl)-1,3-thiazole
• 英文别名: 2-bromo-4-(4-methylsulfanylphenyl)-1,3-thiazole
• CAS: 1222968-56-0
• 化学式: C₁₀H₈BrNS₂
• 分子量: 286.216
• InChiKey: RTGHSUNKHDHMIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Bromo-4-(4-methylsulfanylphenyl)-1,3-thiazole 、 artemisinin 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.66h， 生成
  参考文献：
  名称：

  Thiazole, Oxadiazole, and Carboxamide Derivatives of Artemisinin are Highly Selective and Potent Inhibitors of Toxoplasma gondii

  摘要：

  We have prepared 23 new dehydroartemisinin (DART) trioxane derivatives (11 thiazoles, 2 oxadiazoles, and 10 carboxamides) and have screened them for in vitro activity in the Toxoplasma lytic cycle. Fifteen (65%) of the derivatives were noncytotoxic to host cells (TD50 >= 320 mu M). Eight thiazole derivatives and two carboxamide derivatives displayed effective inhibition of Toxoplasma growth (IC50 = 0.25-0.42 mu M), comparable in potency to artemether (IC50 = 0.31 mu M) and > 100 times more inhibitory than the currently employed front-line drug trimethoprim (IC50 = 46 mu M). The thiazoles as a group were more effective than the other derivatives at inhibiting growth of extracellular as well as intracellular parasites. Unexpectedly, two thiazole trioxanes (5 and 6) were parasiticidal; both inhibited parasite replication irreversibly after parasite exposure to 10 mu M of drug for 24 h, whereas the standard trioxane drugs artemisinin and artemether were not parasiticidal. Some of the new derivatives of artemisinin described here represent effective anti-Toxoplasma trioxanes as well as molecular probes for elucidating the mechanism of action of the DART class of artemisinin derivatives.

  DOI：

  10.1021/jm901857d

文献信息

• Thiazole, Oxadiazole, and Carboxamide Derivatives of Artemisinin are Highly Selective and Potent Inhibitors of <i>Toxoplasma gondii</i>
  作者：Christopher P. Hencken、Lorraine Jones-Brando、Claudia Bordón、Remo Stohler、Bryan T. Mott、Robert Yolken、Gary H. Posner、Lauren E. Woodard

  DOI：10.1021/jm901857d

  日期：2010.5.13

  We have prepared 23 new dehydroartemisinin (DART) trioxane derivatives (11 thiazoles, 2 oxadiazoles, and 10 carboxamides) and have screened them for in vitro activity in the Toxoplasma lytic cycle. Fifteen (65%) of the derivatives were noncytotoxic to host cells (TD50 >= 320 mu M). Eight thiazole derivatives and two carboxamide derivatives displayed effective inhibition of Toxoplasma growth (IC50 = 0.25-0.42 mu M), comparable in potency to artemether (IC50 = 0.31 mu M) and > 100 times more inhibitory than the currently employed front-line drug trimethoprim (IC50 = 46 mu M). The thiazoles as a group were more effective than the other derivatives at inhibiting growth of extracellular as well as intracellular parasites. Unexpectedly, two thiazole trioxanes (5 and 6) were parasiticidal; both inhibited parasite replication irreversibly after parasite exposure to 10 mu M of drug for 24 h, whereas the standard trioxane drugs artemisinin and artemether were not parasiticidal. Some of the new derivatives of artemisinin described here represent effective anti-Toxoplasma trioxanes as well as molecular probes for elucidating the mechanism of action of the DART class of artemisinin derivatives.