1-((Z)-1,2-Diphenyl-but-1-enyl)-4-methanesulfonyl-benzene | 803732-51-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-((Z)-1,2-Diphenyl-but-1-enyl)-4-methanesulfonyl-benzene
• 英文别名: 1-[(Z)-1,2-diphenylbut-1-enyl]-4-methylsulfonylbenzene
• CAS: 803732-51-6
• 化学式: C₂₃H₂₂O₂S
• 分子量: 362.492
• InChiKey: PFWWRKICQHMOAR-FCQUAONHSA-N

物化性质

• 熔点：
  178-180 °C
• 沸点：
  509.2±50.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (4-(methylsulfonyl)phenyl)(phenyl)methanone 、 苯丙酮 在 四氯化钛 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以62%的产率得到1-((Z)-1,2-Diphenyl-but-1-enyl)-4-methanesulfonyl-benzene
  参考文献：
  名称：

  A New Class of Acyclic 2-Alkyl-1,1,2-Triaryl (Z)-Olefins as Selective Cyclooxygenase-2 Inhibitors

  摘要：

  A new class of acyclic (Z)-2-alkyl-1,2-diphenyl-1-(4-methanesulfonylphenyl)ethenes (7) was designed for evaluation as selective cyclooxygenase-2 (COX-2) inhibitors. In vitro COX-1 and COX-2 isozyme inhibition structure-activity studies identified (Z)-1,2-diphenyl-1-(4-methanesulfonylphenyl)oct-1-ene (7d) as a potent COX-2 inhibitor (IC50 = 0.42,muM) with a high COX-2 selectivity index (SI > 234). In a carrageenan-induced rat paw edema assay, (Z)-7d exhibited excellent antiinflammatory activity (ID50 = 1.1 mg/kg). The molecular modeling and structure activity data acquired indicate that (Z)-olefins having cis C-1 4-methanesulfonylphenyl and C-2 unsubstituted phenyl (or 4-acetoxyphenyl) substituents in conjunction with a C-1 phenyl ring and a C-2 alkyl substituent of appropriate length constitute a suitable template for the design of a novel class of acyclic (Z)-2-alkyl-1,1,2-triaryleth-1-ene COX-2 inhibitors.

  DOI：

  10.1021/jm049523y

文献信息

• A New Class of Acyclic 2-Alkyl-1,1,2-Triaryl (<i>Z</i>)-Olefins as Selective Cyclooxygenase-2 Inhibitors
  作者：Md. Jashim Uddin、P. N. Praveen Rao、Robert McDonald、Edward E. Knaus

  DOI：10.1021/jm049523y

  日期：2004.11.1

  A new class of acyclic (Z)-2-alkyl-1,2-diphenyl-1-(4-methanesulfonylphenyl)ethenes (7) was designed for evaluation as selective cyclooxygenase-2 (COX-2) inhibitors. In vitro COX-1 and COX-2 isozyme inhibition structure-activity studies identified (Z)-1,2-diphenyl-1-(4-methanesulfonylphenyl)oct-1-ene (7d) as a potent COX-2 inhibitor (IC50 = 0.42,muM) with a high COX-2 selectivity index (SI > 234). In a carrageenan-induced rat paw edema assay, (Z)-7d exhibited excellent antiinflammatory activity (ID50 = 1.1 mg/kg). The molecular modeling and structure activity data acquired indicate that (Z)-olefins having cis C-1 4-methanesulfonylphenyl and C-2 unsubstituted phenyl (or 4-acetoxyphenyl) substituents in conjunction with a C-1 phenyl ring and a C-2 alkyl substituent of appropriate length constitute a suitable template for the design of a novel class of acyclic (Z)-2-alkyl-1,1,2-triaryleth-1-ene COX-2 inhibitors.