4-(4-Methoxyphenyl)sulfanyl-3,5-dinitrobenzonitrile | 1137560-59-8

• 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-(4-Methoxyphenyl)sulfanyl-3,5-dinitrobenzonitrile
• CAS: 1137560-59-8
• 化学式: C₁₄H₉N₃O₅S
• 分子量: 331.309
• InChiKey: URWJDKXRWTVPBB-UHFFFAOYSA-N

物化性质

• 熔点：
  194-196 °C(Solvent: Dichloromethane; Hexane)
• 沸点：
  449.8±45.0 °C(predicted)
• 密度：
  1.51±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-甲氧基苯硫酚 、 4-氯-3,5-二硝基苯甲腈 在 三乙胺 、 copper(l) iodide 、 新铜试剂 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 以57%的产率得到4-(4-Methoxyphenyl)sulfanyl-3,5-dinitrobenzonitrile
  参考文献：
  名称：

  Redox-active dinitrodiphenylthioethers against Leishmania: Synthesis, structure–activity relationships and mechanism of action studies

  摘要：

  BTB 06237 (2-[(2,4-dichloro-5-methylphenyl)sulfanyl]-1,3-dinitro-5-(trifluoromethyl)benzene), a compound previously identified through QSAR pharmacophore development and a virtual screen of the May-bridge database, possesses potent and selective activity against Leishmania parasites. In the present study, several analogs of BTB 06237 were synthesized and analyzed for activity against Leishmania axenic amastigotes, their ability to reduce the level of parasitemia in peritoneal macrophages, and their ability to generate reactive oxygen species (ROS) in L. donovani promastigotes. It was found that an aromatic ring must be present in the position occupied by the 2,4-dichloro-5-methylphenyl group in the lead compound, but changing the functional groups generally has little effect on the antileishmanial potency. Alterations to the 1,3-dinitro-5-(trifluoromethyl) benzene ring have more influence on antiparasitic activity with two aromatic nitro groups and a third electron-withdrawing group being required. This structural requirement corresponds with redox potential, the ability to generate ROS in the parasites, and dissipation of the mitochondrial membrane potential. Finally, we used this collection of data to design a new antileishmanial compound with strong activity in vitro and improved properties as an antileishmanial candidate. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.11.031