2-(2-benzothiophenyl)-3-(4-(methylsulfonyl)phenyl)-2-cyclopenten-1-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2-(2-benzothiophenyl)-3-(4-(methylsulfonyl)phenyl)-2-cyclopenten-1-one
• 英文别名: 2-(1-Benzothiophen-2-yl)-3-(4-methylsulfonylphenyl)cyclopent-2-en-1-one
• 化学式: C₂₀H₁₆O₃S₂
• 分子量: 368.477
• InChiKey: PIGKNGFMWTUPTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  87.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-乙氧基-2-环戊烯酮 在 sodium tungstate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 正丁基锂 、 硫酸 、 双氧水 、 溴 、 甲基三辛基氯化铵 、 二乙胺 、 三乙胺 、 三苯基膦 作用下， 以 丙醇 、 二氯甲烷 、 氯仿 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 6.5h， 生成 2-(2-benzothiophenyl)-3-(4-(methylsulfonyl)phenyl)-2-cyclopenten-1-one
  参考文献：
  名称：

  2,3-Diarylcyclopentenones as Orally Active, Highly Selective Cyclooxygenase-2 Inhibitors

  摘要：

  Cyclopentenones containing a 4-(methylsulfonyl)phenyl group in the 3-position and a phenyl ring in the 2-position are selective inhibitors of cyclooxygenase-2 (COX-2). The selectivity for COX-2 over COX-1 is dramatically improved by substituting the 2-phenyl group with halogens in the meta position or by replacing the phenyl ring with a 2- or 3-pyridyl ring. Thus the 3,5-difluorophenyl derivative 7 (L1776,967) and the 3-pyridyl derivative 13 (L-784,506) are particularly interesting as potential antiinflammatory agents with reduced side-effect profiles. Both exhibit good oral bioavailability and are potent in standard models of pain, fever, and inflammation yet have a much reduced effect on the GI integrity of rats compared to standard nonsteroidal antiflammatory drugs.

  DOI：

  10.1021/jm980642l

文献信息

• 2,3-Diarylcyclopentenones as Orally Active, Highly Selective Cyclooxygenase-2 Inhibitors
  作者：W. Cameron Black、Christine Brideau、Chi-Chung Chan、Stella Charleson、Nathalie Chauret、David Claveau、Diane Ethier、Robert Gordon、Gillian Greig、Jocelyne Guay、Gregory Hughes、Paule Jolicoeur、Yves Leblanc、Deborah Nicoll-Griffith、Nathalie Ouimet、Denis Riendeau、Denise Visco、Zhaoyin Wang、Lijing Xu、Petpiboon Prasit

  DOI：10.1021/jm980642l

  日期：1999.4.1

  Cyclopentenones containing a 4-(methylsulfonyl)phenyl group in the 3-position and a phenyl ring in the 2-position are selective inhibitors of cyclooxygenase-2 (COX-2). The selectivity for COX-2 over COX-1 is dramatically improved by substituting the 2-phenyl group with halogens in the meta position or by replacing the phenyl ring with a 2- or 3-pyridyl ring. Thus the 3,5-difluorophenyl derivative 7 (L1776,967) and the 3-pyridyl derivative 13 (L-784,506) are particularly interesting as potential antiinflammatory agents with reduced side-effect profiles. Both exhibit good oral bioavailability and are potent in standard models of pain, fever, and inflammation yet have a much reduced effect on the GI integrity of rats compared to standard nonsteroidal antiflammatory drugs.