1,5-dichloro-2-[(2,4-dichloro-5-methylphenyl)disulfanyl]-4-methylbenzene | 88519-69-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,5-dichloro-2-[(2,4-dichloro-5-methylphenyl)disulfanyl]-4-methylbenzene
• CAS: 88519-69-1
• 化学式: C₁₄H₁₀Cl₄S₂
• 分子量: 384.177
• InChiKey: PJXJVCCMXWQPIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,5-dichloro-2-[(2,4-dichloro-5-methylphenyl)disulfanyl]-4-methylbenzene 在 硫酸 、 锌 作用下， 以 水 为溶剂， 生成 2,4-二氯-5-甲基硫代苯酚
  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
• 作为产物：
  描述：

  2,4-二氯-5-甲基氟苯磺酰氯 在 <(C8H17)3NCH3>⁺Cl^- 、 二氧化硫 、 水 、 氢碘酸 作用下， 以93%的产率得到1,5-dichloro-2-[(2,4-dichloro-5-methylphenyl)disulfanyl]-4-methylbenzene
  参考文献：
  名称：

  Bauer, Wolfgang, Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 96, # 1-4, p. 493 - 494

  摘要：

  DOI：

文献信息

• Verfahren zur Herstellung von Disulfiden
  申请人：CASSELLA Aktiengesellschaft

  公开号：EP0093363A1

  公开（公告）日：1983-11-09

  Bei dem Verfahren zur Herstellung von aromatischen, heteroaromatischen oder Farbstoff-Disulfiden durch Reduktion der entsprechenden Sulfochloride mit lodwasserstoffsäure oder mit lodwasserstoffsäure liefernden Substanzen in Gegenwart von Reduktionsmitteln, die lod in lodwasserstoffsäure überführen, wird die Reaktion in einem aus Wasser und einer organischen Phase bestehenden 2-Phasensystem in Gegenwart eines Phasentransferkatalysators durchgeführt.

  在用氢碘酸或在将碘转化为氢碘酸的还原剂存在下用生成氢碘酸的物质还原相应的磺酰氯来制备芳香族、杂芳香族或染料二硫化物的工艺中，反应是在由水和有机相组成的两相体系中，在相转移催化剂存在下进行的。
• Bauer, Wolfgang, Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 96, # 1-4, p. 493 - 494
  作者：Bauer, Wolfgang

  DOI：——

  日期：——
• Redox-active dinitrodiphenylthioethers against Leishmania: Synthesis, structure–activity relationships and mechanism of action studies
  作者：Dawn A. Delfín、Rachel E. Morgan、Xiaohua Zhu、Karl A. Werbovetz

  DOI：10.1016/j.bmc.2008.11.031

  日期：2009.1

  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.