2-((3,4-dimethylphenyl)sulfonyl)acetonitrile | 1008108-48-2

• 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: 2-((3,4-dimethylphenyl)sulfonyl)acetonitrile
• 英文别名: 3,4-dimethyl-phenylsulfonylacetonitrile；[(3,4-Dimethylphenyl)sulfonyl]acetonitrile；2-(3,4-dimethylphenyl)sulfonylacetonitrile
• CAS: 1008108-48-2
• 化学式: C₁₀H₁₁NO₂S
• 分子量: 209.269
• InChiKey: FAJSMMQWWGAXRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  66.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-((3,4-dimethylphenyl)sulfonyl)acetonitrile 、 甲基2-叠氮基苯甲酸酯 在 sodium 作用下， 以 乙醇 为溶剂， 反应 20.33h， 生成
  参考文献：
  名称：

  Solution Phase Parallel Synthesis of Substituted 3-Phenylsulfonyl-[1,2,3]triazolo[1,5-a]quinazolines: Selective Serotonin 5-HT₆ Receptor Antagonists

  摘要：

  Here we present the solution phase parallel synthesis of a combinatorial library consisting of 776 new substituted 3-phenylsulfonyl-[1,2,3]triazolo[1,5-a]quinazolines and a study of the relation of their structure with a 5-HT6 receptor antagonistic activity in a functional cell (HEK 293) analysis and radioligand competitive binding. We have found highly active and selective 5-HT6R antagonists. The most active 5-HT6R antagonists have IC50 < 100 nM in a functional assay, and K-i < 10 nM in a binding assay, which is 100 times higher than the activity with respect to other serotonin receptors.

  DOI：

  10.1021/cc1000049
• 作为产物：
  描述：

  3-azido-2-methylbut-3-en-2-ol 、 {3,4-Me2C6H3N2}{BF4} 在 sodium metabisulfite 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 8.0h， 以75%的产率得到2-((3,4-dimethylphenyl)sulfonyl)acetonitrile
  参考文献：
  名称：

  从焦亚硫酸钠制得2-磺酰基乙腈的简便方法

  摘要：

  描述了在温和条件下四氟硼酸芳基重氮，偏亚硫酸氢钠和3-叠氮基-2-甲基丁-3-烯-2-醇的三组分反应。通过使用大量廉价的焦亚硫酸钠作为二氧化硫替代品，该方案具有良好的官能团相容性，可提供中等至良好收率的2-芳基磺酰基乙腈。反应在室温下平稳进行，不需要任何催化剂或添加剂。此外，该方法的合成效用通过将2-芳基磺酰基乙腈转化为2-芳基磺酰基乙酰胺和2-芳基磺酰基乙胺得到了证明。

  DOI：

  10.1002/adsc.202001243

文献信息

• Synthesis and biological study of 3-(phenylsulfonyl)thieno[2,3-e][1,2,3]triazolo[1,5-a]pyrimidines as potent and selective serotonin 5-HT6 receptor antagonists
  作者：Alexandre V. Ivachtchenko、Elena S. Golovina、Madina G. Kadieva、Angela G. Koryakova、Sergiy M. Kovalenko、Oleg D. Mitkin、Ilya M. Okun、Irina M. Ravnyeyko、Sergey E. Tkachenko、Oleg V. Zaremba

  DOI：10.1016/j.bmc.2010.05.051

  日期：2010.7

  A number of 3-(phenylsulfonyl)thieno[2,3-e][1,2,3]triazolo[1,5-a]pyrimidines were prepared and their 5-HT6 receptor binding affinity and ability to inhibit the functional cellular responses to serotonin were evaluated. 3-[(3-Chlorophenyl)sulfonyl]-N-(tetrahydrofuran-2-ylmethyl)thieno[2,3-e][1,2,3]triazolo[1,5-a]pyrimidin-5-amine 25,26} appeared to be the most active in a functional assay (IC50 = 29

  制备了许多3-（苯磺酰基）噻吩并[2,3- e ] [1,2,3]三唑并[1,5- a ]嘧啶，它们与5-HT 6受体的结合亲和力和抑制细胞功能的能力评估对5-羟色胺的反应。3-[（3-氯苯基）磺酰基] -N-（四氢呋喃-2-基甲基）噻吩并[2,3- e ] [1,2,3]三唑并[1,5 - a ]嘧啶-5-胺2 5，26 }似乎是最活跃的在功能测定法（IC 50  = 29.0纳米）和3-（苯基磺酰基） - ñ - （2-噻吩甲基）噻吩并[2,3- ë ] [1,2,3]三唑并[1,5- a ]嘧啶-5-胺2 1，28 }表明，在5-HT的最大亲和力6受体放射性配体结合测定法（ķ我 = 1.7纳米）。对5-HT 2A和5-HT 2B受体亲和力的筛选显示3-（苯磺酰基）噻吩并[2,3- e ] [1,2,3]三唑并[1,5- a ]嘧啶是高度选择性的5- HT 6受体配体。
• Development of improved inhibitors of wall teichoic acid biosynthesis with potent activity against Staphylococcus aureus
  作者：Kyungae Lee、Jennifer Campbell、Jonathan G. Swoboda、Gregory D. Cuny、Suzanne Walker

  DOI：10.1016/j.bmcl.2010.01.036

  日期：2010.3

  A small molecule (1835F03) that inhibits Staphylococcus aureus wall teichoic acid biosynthesis, a proposed antibiotic target, has been discovered. Rapid, parallel, solution-phase synthesis was employed to generate a focused library of analogs, providing detailed information about structure-activity relationships and leading to the identification of targocil, a potent antibiotic. (C) 2010 Elsevier Ltd. All rights reserved.
• A Concise Route to 2‐Sulfonylacetonitriles from Sodium Metabisulfite
  作者：Yanfang Yao、Ziqing Yin、Weiyun Chen、Wenlin Xie、Fu‐Sheng He、Jie Wu

  DOI：10.1002/adsc.202001243

  日期：2021.1.19

  A three‐component reaction of aryldiazonium tetrafluoroborates, sodium metabisulfite, and 3‐azido‐2‐methylbut‐3‐en‐2‐ol under mild conditions is described. By using abundant and cheap sodium metabisulfite as the sulfur dioxide surrogate, this protocol features good functional group compatibility, affording 2‐arylsulfonylacetonitriles in moderate to good yields. The reaction proceeds smoothly at room

  描述了在温和条件下四氟硼酸芳基重氮，偏亚硫酸氢钠和3-叠氮基-2-甲基丁-3-烯-2-醇的三组分反应。通过使用大量廉价的焦亚硫酸钠作为二氧化硫替代品，该方案具有良好的官能团相容性，可提供中等至良好收率的2-芳基磺酰基乙腈。反应在室温下平稳进行，不需要任何催化剂或添加剂。此外，该方法的合成效用通过将2-芳基磺酰基乙腈转化为2-芳基磺酰基乙酰胺和2-芳基磺酰基乙胺得到了证明。
• Solution Phase Parallel Synthesis of Substituted 3-Phenylsulfonyl-[1,2,3]triazolo[1,5-<i>a</i>]quinazolines: Selective Serotonin 5-HT₆ Receptor Antagonists
  作者：Alexandre V. Ivachtchenko、Elena S. Golovina、Madina G. Kadieva、Angela G. Koryakova、Sergiy M. Kovalenko、Oleg D. Mitkin、Ilya M. Okun、Irina M. Ravnyeyko、Sergey E. Tkachenko、Oleg V. Zaremba

  DOI：10.1021/cc1000049

  日期：2010.7.12

  Here we present the solution phase parallel synthesis of a combinatorial library consisting of 776 new substituted 3-phenylsulfonyl-[1,2,3]triazolo[1,5-a]quinazolines and a study of the relation of their structure with a 5-HT6 receptor antagonistic activity in a functional cell (HEK 293) analysis and radioligand competitive binding. We have found highly active and selective 5-HT6R antagonists. The most active 5-HT6R antagonists have IC50 < 100 nM in a functional assay, and K-i < 10 nM in a binding assay, which is 100 times higher than the activity with respect to other serotonin receptors.