(Z)-4-[(4-hydroxyphenyl)sulfanyl]but-3-en-2-one | 1176996-15-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (Z)-4-[(4-hydroxyphenyl)sulfanyl]but-3-en-2-one
• 英文别名: (Z)-4-(4-hydroxyphenyl)sulfanylbut-3-en-2-one
• CAS: 1176996-15-8
• 化学式: C₁₀H₁₀O₂S
• 分子量: 194.254
• InChiKey: BMACTJGPAGQQPO-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-4-[(4-hydroxyphenyl)sulfanyl]but-3-en-2-one 在 氧气 、 酪氨酸酶 作用下， 生成
  参考文献：
  名称：

  Synthesis and Preliminary in Vitro Biological Evaluation of 4-[(4-Hydroxyphenyl)sulfanyl]but-3-en-2-one, a 4-Mercaptophenol Derivative Designed As a Novel Bifunctional Antimelanoma Agent

  摘要：

  We report the synthesis and preliminary in vitro biological evaluations of 4-[(4-hydroxyphenyl)sulfanyl]but-3-en-2-one, a compound designed as a potential bifunctional antimelanoma agent, bearing both a tyrosinase-activa table phenolic moiety and a GSH-reactive alpha,beta-unsaturated carbonyl group. Both the E (1) and Z (2) isomers of the synthesized compound proved to be very good substrates of mushroom tyrosinase, reacted quickly with GSH at physiological pH, and showed a significant cytotoxic activity against B16F1 murine melanoma cells.

  DOI：

  10.1021/jm900642j
• 作为产物：
  描述：

  4-羟基苯硫酚 、 3-丁炔-2-酮 以 二甲基亚砜 为溶剂， 反应 0.5h， 生成 (Z)-4-[(4-hydroxyphenyl)sulfanyl]but-3-en-2-one 、 (E)-4-[(4-hydroxyphenyl)sulfanyl]but-3-en-2-one
  参考文献：
  名称：

  Synthesis and Preliminary in Vitro Biological Evaluation of 4-[(4-Hydroxyphenyl)sulfanyl]but-3-en-2-one, a 4-Mercaptophenol Derivative Designed As a Novel Bifunctional Antimelanoma Agent

  摘要：

  We report the synthesis and preliminary in vitro biological evaluations of 4-[(4-hydroxyphenyl)sulfanyl]but-3-en-2-one, a compound designed as a potential bifunctional antimelanoma agent, bearing both a tyrosinase-activa table phenolic moiety and a GSH-reactive alpha,beta-unsaturated carbonyl group. Both the E (1) and Z (2) isomers of the synthesized compound proved to be very good substrates of mushroom tyrosinase, reacted quickly with GSH at physiological pH, and showed a significant cytotoxic activity against B16F1 murine melanoma cells.

  DOI：

  10.1021/jm900642j