N,N'-(diselanediyldibenzene-4,1-diyl)bis[4-(trifluoromethyl)benzenesulfonamide] | 1579196-45-4

• 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: N,N'-(diselanediyldibenzene-4,1-diyl)bis[4-(trifluoromethyl)benzenesulfonamide]
• 英文别名: 4-(trifluoromethyl)-N-[4-[[4-[[4-(trifluoromethyl)phenyl]sulfonylamino]phenyl]diselanyl]phenyl]benzenesulfonamide
• CAS: 1579196-45-4
• 化学式: C₂₆H₁₈F₆N₂O₄S₂Se₂
• 分子量: 758.482
• InChiKey: IMVLGCWEGQXIJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  42.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  92.34
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  4-aminophenylselenocyanate 在 sodium tetrahydroborate 作用下， 以 乙醚 、 乙醇 为溶剂， 生成 N,N'-(diselanediyldibenzene-4,1-diyl)bis[4-(trifluoromethyl)benzenesulfonamide]
  参考文献：
  名称：

  Novel hybrid selenosulfonamides as potent antileishmanial agents

  摘要：

  Diselenide and sulfonamide derivatives have recently attracted considerable interest as leishmanicidal agents in drug discovery. In this study, a novel series of sixteen hybrid selenosulfonamides has been synthesized and screened for their in vitro activity against Leishmania infantum intracellular amastigotes and THP-1 cells. These assays revealed that most of the compounds exhibited antileishmanial activity in the low micromolar range and led us to identify three lead compounds (derivatives 2, 7 and 14) with IC50 values ranging from 0.83 to 1.47 mu M and selectivity indexes (SI) over 17, much higher than those observed for the reference drugs miltefosine and edelfosine. When evaluated against intracellular amastigotes, hybrid compound 7 emerged as the most active compound (IC50 = 2.8 mu M), showing higher activity and much less toxicity against THP-1 cells than edelfosine. These compounds could potentially serve as templates for future drug-optimization and drug-development efforts for their use as therapeutic agents in developing countries. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.030

文献信息

• Novel hybrid selenosulfonamides as potent antileishmanial agents
  作者：Ylenia Baquedano、Esther Moreno、Socorro Espuelas、Paul Nguewa、María Font、Kilian Jesús Gutierrez、Antonio Jiménez-Ruiz、Juan Antonio Palop、Carmen Sanmartín

  DOI：10.1016/j.ejmech.2013.12.030

  日期：2014.3

  Diselenide and sulfonamide derivatives have recently attracted considerable interest as leishmanicidal agents in drug discovery. In this study, a novel series of sixteen hybrid selenosulfonamides has been synthesized and screened for their in vitro activity against Leishmania infantum intracellular amastigotes and THP-1 cells. These assays revealed that most of the compounds exhibited antileishmanial activity in the low micromolar range and led us to identify three lead compounds (derivatives 2, 7 and 14) with IC50 values ranging from 0.83 to 1.47 mu M and selectivity indexes (SI) over 17, much higher than those observed for the reference drugs miltefosine and edelfosine. When evaluated against intracellular amastigotes, hybrid compound 7 emerged as the most active compound (IC50 = 2.8 mu M), showing higher activity and much less toxicity against THP-1 cells than edelfosine. These compounds could potentially serve as templates for future drug-optimization and drug-development efforts for their use as therapeutic agents in developing countries. (C) 2014 Elsevier Masson SAS. All rights reserved.