2-mercapto-4-methylbenzonitrile | 613263-26-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚类
• 英文名称: 2-mercapto-4-methylbenzonitrile
• 英文别名: 4-Methyl-2-sulfanylbenzonitrile
• CAS: 613263-26-6
• 化学式: C₈H₇NS
• 分子量: 149.216
• InChiKey: WWBWUJWSDYGPDQ-UHFFFAOYSA-N

物化性质

• 熔点：
  38-40 °C
• 沸点：
  296.6±28.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  24.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-mercapto-4-methylbenzonitrile 在 potassium tert-butylate 、 双氧水 、 溶剂黄146 、 三乙胺 作用下， 以 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 生成 9-methylbenzothieno[3,2-c]isoquinolin-5(6H)-one 11-oxide
  参考文献：
  名称：

  取代苯并噻吩并 [3,2-c]isoquinolin-5(6H)-ones 及其亚磺酰基和磺酰基衍生物的合成

  摘要：

  提出了一种以良好收率合成取代苯并噻吩并[3,2-c]异喹啉-5(6H)-酮的方法，该方法包括取代的2-巯基苯甲腈与2-(氯甲基)苯甲酸甲酯和随后用叔丁醇钾处理得到的缩合产物。缩合产物氧化为亚砜或砜，随后用叔丁醇钾处理这些化合物，生成取代的苯并噻吩并[3,2-c]异喹啉-5(6H)-one 11-氧化物或取代的苯并噻吩并[3,2] -c]isoquinolin-5(6H)-一种具有良好产率的 11,11-二氧化物。

  DOI：

  10.1007/s11172-014-0765-6
• 作为产物：
  描述：

  4-甲基-2-硝基苯腈 在 aluminum (III) chloride 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.0h， 生成 2-mercapto-4-methylbenzonitrile
  参考文献：
  名称：

  取代的苄硫醚：它们的环回复特性的合成和量子化学研究。

  摘要：

  开发了不需要快速真空热解的高度取代苯并硫代酸酯的灵活合成方法。这允许使用许多官能团和不可蒸发的分子。分离出高度稳定的衍生物。通过密度泛函方法评估了各种苯硫醚的分子轨道特性。比较了四元环的环还原机理与含氧类似物的环还原机理。

  DOI：

  10.1021/acs.orglett.0c01261

文献信息

• Synthesis and biological evaluation of 2-(3′,4′,5′-trimethoxybenzoyl)-3-aryl/arylaminobenzo[b]thiophene derivatives as a novel class of antiproliferative agents
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Carlota Lopez Cara、Ernest Hamel、Giuseppe Basso、Roberta Bortolozzi、Giampietro Viola

  DOI：10.1016/j.ejmech.2010.09.038

  日期：2010.12

  the B-ring, was synthesized and evaluated for antiproliferative activity, inhibition of tubulin polymerization and cell cycle effects. The most promising compound in this series was 2-(3′,4′,5′-trimethoxybenzoyl)-3-(4′-ethoxyphenyl)-benzo[b]thiophene (4e), which significantly inhibited cancer cell growth at submicromolar concentrations, especially against HeLa and Jurkat cells, and interacted with tubulin

  微管在有丝分裂和间期的生物学重要性使它们成为开发抗癌剂的有趣目标。苯并[ b ]噻吩等小分子作为微管蛋白聚合的抑制剂很有吸引力。因此，一类新的化合物结合了 2-(3',4',5'-三甲氧基苯甲酰基)-3-芳基/芳氨基苯并[ b ]噻吩分子骨架的结构基序，具有给电子（Me, OMe 、SMe 或 OEt) 或 B 环上的吸电子（F 和 Cl）取代基，合成并评估其抗增殖活性、抑制微管蛋白聚合和细胞周期效应。该系列中最有前途的化合物是2-(3',4',5'-三甲氧基苯甲酰基)-3-(4'-乙氧基苯基)-苯并[ b ]噻吩(4e )，在亚微摩尔浓度下显着抑制癌细胞生长，尤其是对 HeLa 和 Jurkat 细胞的抑制，并与微管蛋白相互作用。通过流式细胞术分析确定，4e以时间和浓度依赖性方式引起 G2/M 期阻滞和细胞凋亡。G2/M 的阻断与细胞周期蛋白 B1 的表达增加和 cdc25c 的磷酸化相关。此外，4e扰乱线粒体膜电位并引起
• Synthesis of substituted 5-aminobenzothieno[3,2-c]isoquinolines and their sulfinyl and sulfonyl derivatives
  作者：V. E. Kalugin、A. M. Shestopalov

  DOI：10.1007/s11172-015-0948-9

  日期：2015.4

  A method for the preparation of substituted 5-aminobenzothieno[3,2-c]isoquinolines in good yields by the condensation of substituted 2-mercaptobenzonitriles with 2-(chloromethyl)benzonitrile and a subsequent treatment of the condensation products with potassium tert-butoxide was suggested. The oxidation of the condensation products to sulfoxides or sulfones and a subsequent treatment of these compounds

  通过将取代的 2-巯基苯甲腈与 2-(氯甲基) 苯甲腈缩合，然后用叔丁醇钾处理缩合产物，以良好收率制备取代的 5-氨基苯并噻吩并 [3,2-c] 异喹啉的方法是建议。缩合产物氧化为亚砜或砜，随后用叔丁醇钾处理这些化合物，制备出取代的 5-氨基苯并噻吩并 [3,2-c] 异喹啉 11-氧化物或 5-氨基苯并噻吩并 [3,2] -c]异喹啉 11,11-二氧化物，收率良好。
• Synthesis and preliminary biological evaluation of new anti-tubulin agents containing different benzoheterocycles
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、M. Katherine Jung、Maria Antonietta Iaconinoto、Maria Dora Carrion、Vincent Remusat、Delia Preti、Mojgan Aghazadeh Tabrizi、Fruttarolo Francesca、Erik De Clercq、Jan Balzarini、Ernest Hamel

  DOI：10.1016/j.bmcl.2005.06.022

  日期：2005.9

  A new series of compounds, in which the 2-amino-4-methoxyphenyl ring of phenstatin analogue 5 was replaced with 2- or 3-amino-benzoheterocycles, was synthesized and evaluated for antiproliferative activity and inhibition of colchicine binding. The lack of activity of 3 ',4 '-dimethoxy- and 4 '-methoxy-benzoyl derivatives (8 and 9, respectively) indicates that the 3 ',4 ',5 '-trimethoxybenzoyl moiety is critical for the activity. Two compounds, 7 and 11, displayed potent antiproliferative activity, with IC50 values ranging from 25 to 100 nM against a variety of cancer cell lines. Derivative 11 was more active than CA-4 as an inhibitor of tubulin polymerization. The results demonstrated that the antiproliferative activity was correlated with inhibition of tubulin polymerization. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and Biological Evaluation of 2- and 3-Aminobenzo[<i>b</i>]thiophene Derivatives as Antimitotic Agents and Inhibitors of Tubulin Polymerization
  作者：Romeo Romagnoli、Pier Giovanni Baraldi、Maria Dora Carrion、Carlota Lopez Cara、Delia Preti、Francesca Fruttarolo、Maria Giovanna Pavani、Mojgan Aghazadeh Tabrizi、Manlio Tolomeo、Stefania Grimaudo、Antonella Di Cristina、Jan Balzarini、John A. Hadfield、Andrea Brancale、Ernest Hamel

  DOI：10.1021/jm070050f

  日期：2007.5.1

  Two new series of inhibitors of tubulin polymerization based on the 2-amino-3-(3,4,5-trimethoxybenzoyl)benzo[b]thiophene molecular skeleton and its 3-amino positional isomer were synthesized and evaluated for antiproliferative activity, inhibition of tubulin polymerization, and cell cycle effects. Although many more 3-amino derivatives have been synthesized so far, the most promising compound in this series was 2-amino-6-methyl-3-(3,4,5-trimethoxybenzoyl)benzo[b]thiophene, which inhibits cancer cell growth at subnanomolar concentrations and interacts strongly with tubulin by binding to the colchicine site.
• [EN] INHIBITORS OF 5-LIPOXYGENASE<br/>[FR] INHIBITEURS DE LA 5-LIPOXYGÉNASE
  申请人：AMIRA PHARMACEUTICALS INC

  公开号：WO2011109679A2

  公开（公告）日：2011-09-09

  Described herein are compounds and pharmaceutical compositions containing such compounds, which inhibit the activity of 5-lipoxygenase (5-LO). Also described herein are methods of using such 5-LO inhibitors, alone and in combination with other compounds, for treating respiratory, cardiovascular, and other leukotriene-dependent or leukotriene mediated conditions, diseases, or disorders.