[2-[(E)-2-(4-chlorophenyl)ethenyl]sulfanylphenyl] acetate | 847258-37-1

• 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: [2-[(E)-2-(4-chlorophenyl)ethenyl]sulfanylphenyl] acetate
• CAS: 847258-37-1
• 化学式: C₁₆H₁₃ClO₂S
• 分子量: 304.797
• InChiKey: AJGHUQDTKWXSBL-ZHACJKMWSA-N

物化性质

• 熔点：
  86-88 °C
• 沸点：
  437.3±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [2-[(E)-2-(4-chlorophenyl)ethenyl]sulfanylphenyl] acetate 在 双氧水 、 溶剂黄146 作用下， 反应 16.0h， 以86%的产率得到
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of (E)- and (Z)-styryl-2-acetoxyphenyl sulfides and sulfones as cyclooxygenase-2 inhibitors

  摘要：

  A new series of styryl acetoxyphenyl sulfides and sulfones possessing (E)- and (Z)-configurations were designed and prepared by stereospecific syntheses. All these compounds were evaluated for their ability to inhibit COX-2 enzyme in vitro. Structure-activity relationship studies on these compounds revealed that only sulfides with (Z)-configuration have potential COX-2 inhibitory activity. This inactivation of the enzyme is believed to be due to the selective covalent modification of COX-2 by the inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.005
• 作为产物：
  描述：

  2-羟基苯硫酚 在 吡啶 、 manganese triacetate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 6.03h， 生成 [2-[(E)-2-(4-chlorophenyl)ethenyl]sulfanylphenyl] acetate
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of (E)- and (Z)-styryl-2-acetoxyphenyl sulfides and sulfones as cyclooxygenase-2 inhibitors

  摘要：

  A new series of styryl acetoxyphenyl sulfides and sulfones possessing (E)- and (Z)-configurations were designed and prepared by stereospecific syntheses. All these compounds were evaluated for their ability to inhibit COX-2 enzyme in vitro. Structure-activity relationship studies on these compounds revealed that only sulfides with (Z)-configuration have potential COX-2 inhibitory activity. This inactivation of the enzyme is believed to be due to the selective covalent modification of COX-2 by the inhibitors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.005

文献信息

• (Z)-STYRYL ACETOXYPHENYL SULFIDES AS CYCLOOXYGENASE INHIBITORS
  申请人：Temple University of the CommonwealthSystem of Higher Education

  公开号：EP1191929A2

  公开（公告）日：2002-04-03
• EP1191929A4
  申请人：——

  公开号：EP1191929A4

  公开（公告）日：2005-02-16
• US6656968B1
  申请人：——

  公开号：US6656968B1

  公开（公告）日：2003-12-02
• [EN] (Z)-STYRYL ACETOXYPHENYL SULFIDES AS CYCLOOXYGENASE INHIBITORS<br/>[FR] (Z)-STYRYL ACETOXYPHENYLE SULFURES COMME INHIBITEURS DE LA CYCLO-OXYGENASE
  申请人：UNIV TEMPLE

  公开号：WO2000077169A2

  公开（公告）日：2000-12-21

  Compounds of formula (I) are provided wherein R1, R2, R3 and R4 are independently selected from the group consisting of hydrogen, halogen, hydroxyl, C1-C8 alkyl, C1-C6 alkoxy, nitro, cyano, acetoxy, amino, carboxy, sulfamyl, lower acylsulfamyl and trifluoromethyl. The compounds are inhibitors of cyclooxygenase-2 activity, useful for treating inflamation and cyclooxygenase-mediated disorders.