4-[2-(4-bromophenyl)-2-oxoethylsulfonyl]benzonitrile | 1253695-39-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[2-(4-bromophenyl)-2-oxoethylsulfonyl]benzonitrile
• CAS: 1253695-39-4
• 化学式: C₁₅H₁₀BrNO₃S
• 分子量: 364.219
• InChiKey: CGSDUKIZBRGZEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  75.0
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-甲基-3-苯基-1-丙烯 、 4-[2-(4-bromophenyl)-2-oxoethylsulfonyl]benzonitrile 在 copper diacetate 、 manganese(III) triacetate dihydrate 、 溶剂黄146 作用下， 反应 0.75h， 以10%的产率得到4-[5-benzyl-2-(4-bromophenyl)-5-methyl-4,5-dihydrofuran-3-ylsulfonyl]benzonitrile
  参考文献：
  名称：

  Synthesis and evaluation of original amidoximes as antileishmanial agents

  摘要：

  An original series of amidoxime derivatives was synthesized using manganese(III) acetate, Buchwald-Hartwig and Heck reactions. Two amidoximes (39 and 52) showed interesting in vitro activities toward Leishmania donovani promastigotes, exhibiting 8.3 and 8.8 mu M IC50 values. Moreover, the cytotoxicity of these compounds was evaluated on human THP1 cells, giving access to the corresponding selectivity index. Among the 25 tested compounds, amidoximes 38 and 39 and diamidoximes 50 and 52 exhibited a better selectivity index than pentamidine used as a drug compound reference. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.099
• 作为产物：
  描述：

  2,4'-二溴苯乙酮 、 4-氰基苯磺酰氯 在 碳酸氢钠 、 sodium sulfite 作用下， 以 水 、 乙醇 为溶剂， 反应 0.5h， 以77%的产率得到4-[2-(4-bromophenyl)-2-oxoethylsulfonyl]benzonitrile
  参考文献：
  名称：

  Synthesis and evaluation of monoamidoxime derivatives: Toward new antileishmanial compounds

  摘要：

  A new series of monoamidoxime derivatives was synthesized using manganese(III) acetate by microwave irradiation. Several amidoximes (27-31, 33, 38) showed valuable in vitro activities toward Leishmania donovani promastigotes, exhibiting IC50 values between 5.21 and 7.89 mu M. In parallel, the cytotoxicity of these compounds was evaluated on murine J774A.1 cells, revealing the corresponding selectivity index (SI). Among the 13 tested compounds, 4 monoamidoximes (27-30) exhibited an SI more than 20 times better than pentamidine. Moreover, monoamidoxime 28 (4-[5-Benzyl-3-(4-fluorophenylsulfonyl)-5-methyl-4,5-dihydrofuran-2-yl]-N'-hydroxybenzimidamide) is 40 times more selective than pentamidine, and 1.6 times more than amphotericin B, used as reference drug compounds. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.026