Z-styryl 2-acetoxyphenylsulfide | 313269-63-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: Z-styryl 2-acetoxyphenylsulfide
• 英文别名: [2-[(Z)-2-phenylethenyl]sulfanylphenyl] acetate
• CAS: 313269-63-5
• 化学式: C₁₆H₁₄O₂S
• 分子量: 270.352
• InChiKey: CNPKTIFLHWLESM-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 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：

  Z-styryl 2-acetoxyphenylsulfide 在 双氧水 、 溶剂黄146 作用下， 反应 16.0h， 以88%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 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 Z-styryl 2-acetoxyphenylsulfide
  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 Commonwealth System of Higher Education

  公开号：US06656968B1

  公开（公告）日：2003-12-02

  Compounds of the formula 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 inflammation and cyclooxygenase-mediated disorders.

  提供了一种化合物的通式，其中R1、R2、R3和R4各自独立地选自氢、卤素、羟基、C1-C8烷基、C1-C6烷氧基、硝基、氰基、乙酰氧基、氨基、羧基、磺酰胺基、低级酰基磺酰胺基和三氟甲基。这些化合物是环氧合酶-2活性的抑制剂，可用于治疗炎症和环氧合酶介导的疾病。