(E)-3-(4-(methylsulfonyl)styryl)furan | 1259295-35-6

• 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)-3-(4-(methylsulfonyl)styryl)furan
• 英文别名: 3-[(E)-2-(4-methylsulfonylphenyl)ethenyl]furan
• CAS: 1259295-35-6
• 化学式: C₁₃H₁₂O₃S
• 分子量: 248.302
• InChiKey: QQRVCKLIZGPTIJ-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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：
  55.7
• 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)-3-(4-(methylsulfonyl)styryl)furan 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以42%的产率得到(E)-(2-((4-(2-(furan-3-yl)vinyl)phenyl)sulfonyl)ethyl)trimethylsilane
  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：

  (E)-3-(4-(methylthio)styryl)furan 在 Oxone 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-3-(4-(methylsulfonyl)styryl)furan
  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

文献信息

• 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.