(E)-2-(4-(methylsulfonyl)styryl)thiophene | 1259295-36-7

• 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: (E)-2-(4-(methylsulfonyl)styryl)thiophene
• 英文别名: 2-[(E)-2-(4-methylsulfonylphenyl)ethenyl]thiophene
• CAS: 1259295-36-7
• 化学式: C₁₃H₁₂O₂S₂
• 分子量: 264.369
• InChiKey: JTGRXCMSCWBAQN-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  70.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  碘甲基三甲基硅烷 、 (E)-2-(4-(methylsulfonyl)styryl)thiophene 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以50%的产率得到(E)-trimethyl(2-((4-(2-(thiophen-2-yl)vinyl)phenyl)sulfonyl)ethyl)silane
  参考文献：
  名称：

  Sulfonamide derivatives of styrylheterocycles as a potent inhibitor of COX-2-mediated prostaglandin E2 production

  摘要：

  The overproduction of prostaglandin E-2 (PGE(2)) plays an important role in a variety of pathophysiological processes including inflammation and carcinogenesis. Therefore, the modulation of PGE(2) production is a promising target in the design of chemotherapeutic agents. In the present study, the inhibitory effects of a series of styrylheterocycles having either a p-SO2NH2 or p-SO2Me group on the production of cyclooxygenase-2-mediated PGE(2) were evaluated in lipopolysaccharide-stimulated RAW264.7 murine macrophages. Among the series of styrylheterocycle derivatives, (E)-4-(2-(thiophen-3-yl)vinyl) benzenesulfonamide exhibited a potent inhibitory activity, with an IC50 value of 0.013 mu M. The inhibitory activity against the overproduction of PGE(2) by the active compound was found to be due in part to the suppression of COX-2 mRNA expression. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.09.136
• 作为产物：
  描述：

  对甲砜基苯甲醛 在 potassium fluoride 、 bis(1,5-cyclooctadiene)nickel (0) 、 N,N-二甲基乙酰胺 、 三乙胺 、 亚磷酸二甲酯 、 三苯基膦 、 4,4'-二叔丁基-2,2'-二吡啶 、 sodium hydroxide 、 magnesium chloride 、 锌 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 17.5h， 生成 (E)-2-(4-(methylsulfonyl)styryl)thiophene
  参考文献：
  名称：

  镍卤化物与乙烯基溴的镍催化还原偶联制备乙烯基芳烃

  摘要：

  这项工作强调了在温和且易于操作的镍催化反应条件下，通过芳基卤化物与乙烯基溴的还原偶联来合成取代的乙烯基芳烃。广泛使用的芳基卤化物，包括杂芳族化合物和乙烯基溴化物，以中等至优异的收率生产了具有高官能团耐受性的产品。镍催化系统在两个C（sp 2）-卤化物偶合体之间显示出良好的化学选择性，从而证明了不同于其他逐步方案的机理途径。

  DOI：

  10.1002/anie.201607959

文献信息

• Preparation of Vinyl Arenes by Nickel-Catalyzed Reductive Coupling of Aryl Halides with Vinyl Bromides
  作者：Jiandong Liu、Qinghua Ren、Xinghua Zhang、Hegui Gong

  DOI：10.1002/anie.201607959

  日期：2016.12.12

  This work emphasizes the synthesis of substituted vinyl arenes by reductive coupling of aryl halides with vinyl bromides under mild and easy‐to‐operate nickel‐catalyzed reaction conditions. A broad range of aryl halides, including heteroaromatics, and vinyl bromides were employed to yielding products in moderate to excellent yields with high functional‐group tolerance. The nickel‐catalytic system displays

  这项工作强调了在温和且易于操作的镍催化反应条件下，通过芳基卤化物与乙烯基溴的还原偶联来合成取代的乙烯基芳烃。广泛使用的芳基卤化物，包括杂芳族化合物和乙烯基溴化物，以中等至优异的收率生产了具有高官能团耐受性的产品。镍催化系统在两个C（sp 2）-卤化物偶合体之间显示出良好的化学选择性，从而证明了不同于其他逐步方案的机理途径。
• Sulfonamide derivatives of styrylheterocycles as a potent inhibitor of COX-2-mediated prostaglandin E2 production
  作者：Chaemin Lim、Minhee Lee、Eun-Jung Park、Ran Cho、Hyen-Joo Park、Seong Jin Lee、Heeyeong Cho、Sang Kook Lee、Sanghee Kim

  DOI：10.1016/j.bmcl.2010.09.136

  日期：2010.12

  The overproduction of prostaglandin E-2 (PGE(2)) plays an important role in a variety of pathophysiological processes including inflammation and carcinogenesis. Therefore, the modulation of PGE(2) production is a promising target in the design of chemotherapeutic agents. In the present study, the inhibitory effects of a series of styrylheterocycles having either a p-SO2NH2 or p-SO2Me group on the production of cyclooxygenase-2-mediated PGE(2) were evaluated in lipopolysaccharide-stimulated RAW264.7 murine macrophages. Among the series of styrylheterocycle derivatives, (E)-4-(2-(thiophen-3-yl)vinyl) benzenesulfonamide exhibited a potent inhibitory activity, with an IC50 value of 0.013 mu M. The inhibitory activity against the overproduction of PGE(2) by the active compound was found to be due in part to the suppression of COX-2 mRNA expression. (C) 2010 Elsevier Ltd. All rights reserved.