4-(2-((4-bromophenyl)sulfonyl)acetyl)benzonitrile | 654676-92-3

• 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)sulfonyl)acetyl)benzonitrile
• 英文别名: 4-[2-(4-bromophenylsulfonyl)acetyl]benzonitrile；(4-bromophenylsulphonylmethyl)-(4-cyanophenyl)-ketone；4-[2-(4-bromophenyl)sulfonylacetyl]benzonitrile
• CAS: 654676-92-3
• 化学式: C₁₅H₁₀BrNO₃S
• 分子量: 364.219
• InChiKey: VYVIGJUPOMUACJ-UHFFFAOYSA-N

物化性质

• 沸点：
  591.4±50.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 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：

  4-(2-((4-bromophenyl)sulfonyl)acetyl)benzonitrile 、 2-甲基-3-苯基-1-丙烯 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-3-(4-bromophenylsulfonyl)-5-methyl-4,5-dihydrofuran-2-yl]-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'-氰基苯乙酮 、 4-溴苯磺酰氯 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-bromophenyl)sulfonyl)acetyl)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

• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSES CHIMIQUES
  申请人：ASTRAZENECA AB

  公开号：WO2004011410A1

  公开（公告）日：2004-02-05

  Compounds of formula (I):wherein variable groups are as defined within; for use in the inhibition of 11βHSD1 are described.

  式(I)的化合物：其中变量基团如定义内；用于抑制11βHSD1。
• Functionalization of Alkynes and Alkenes Using a Cascade Reaction Approach: Synthesis of β-Keto Sulfones under Metal-free Conditions
  作者：Mukesh Kumar、Riyaz Ahmed、Maninder Singh、Shweta Sharma、Thanusha Thatikonda、Parvinder Pal Singh

  DOI：10.1021/acs.joc.9b02779

  日期：2020.1.17

  reporting a multicomponent cascade reaction approach for the synthesis of β-keto sulfones by exploiting differential reactivity pattern of substrates under open-atmosphere and metal-free conditions. The coupling partners are aryldiazonium salts, unsaturated compounds, and DABSO. The optimized conditions worked well with both alkenes and alkynes. Moreover, the reaction also works with metabisulfite for

  在这里，我们正在报道一种在开放气氛和无金属条件下通过利用底物的不同反应模式来合成β-酮砜的多组分级联反应方法。偶联伙伴是芳基重氮盐，不饱和化合物和DABSO。优化的条件对烯烃和炔烃都适用。此外，该反应还与焦亚硫酸盐一起用作砜的来源。受控液相色谱-质谱法和18 O标记的实验表明，空气是β-酮砜的酮基上引入的氧原子的来源。
• Ketones
  申请人：Barton John Peter

  公开号：US20050272036A1

  公开（公告）日：2005-12-08

  Compounds of formula (I): wherein variable groups are as defined within; for use in the inhibition of 11βHSD1 are described.

  描述了式(I)的化合物：其中变量基团如定义的那样；用于抑制11βHSD1。
• Synthesis and evaluation of original amidoximes as antileishmanial agents
  作者：Ahlem Bouhlel、Christophe Curti、Aurélien Dumètre、Michèle Laget、Maxime D. Crozet、Nadine Azas、Patrice Vanelle

  DOI：10.1016/j.bmc.2010.06.099

  日期：2010.10.15

  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.
• 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.