4-[2-(4-chlorophenyl)-2-oxoethylsulfonyl]benzonitrile | 1313054-99-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[2-(4-chlorophenyl)-2-oxoethylsulfonyl]benzonitrile
• 英文别名: 4-[2-(4-Chlorophenyl)-2-oxoethyl]sulfonylbenzonitrile
• CAS: 1313054-99-7
• 化学式: C₁₅H₁₀ClNO₃S
• 分子量: 319.768
• InChiKey: FFRNJFHEJIKPBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  83.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-甲基-3-苯基-1-丙烯 、 4-[2-(4-chlorophenyl)-2-oxoethylsulfonyl]benzonitrile 在 盐酸羟胺 、 potassium tert-butylate 、 copper diacetate 、 manganese(III) triacetate dihydrate 、 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 反应 12.75h， 生成 4-[5-benzyl-2-(4-chlorophenyl)-5-methyl-4,5-dihydrofuran-3-ylsulfonyl]-N'-hydroxybenzimidamide
  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
• 作为产物：
  描述：

  2'-溴-4-氯苯乙酮 、 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68%的产率得到4-[2-(4-chlorophenyl)-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

文献信息

• Synthesis and evaluation of monoamidoxime derivatives: Toward new antileishmanial compounds
  作者：Lucie Paloque、Ahlem Bouhlel、Christophe Curti、Aurélien Dumètre、Pierre Verhaeghe、Nadine Azas、Patrice Vanelle

  DOI：10.1016/j.ejmech.2011.04.026

  日期：2011.7

  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.