5-bromo-4-hydroxy-2-phenyl-2-(phenylsulfanylmethyl)-3H-pyran-6-one | 959425-63-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-bromo-4-hydroxy-2-phenyl-2-(phenylsulfanylmethyl)-3H-pyran-6-one
• CAS: 959425-63-9
• 化学式: C₁₈H₁₅BrO₃S
• 分子量: 391.285
• InChiKey: PKRZDFMEEFGAAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  邻氯苯硫酚 、 5-bromo-4-hydroxy-2-phenyl-2-(phenylsulfanylmethyl)-3H-pyran-6-one 在 哌啶 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以368 mg的产率得到3-(2-chlorophenylthio)-5,6-dihydro-4-hydroxy-6-phenyl-6-((phenylthio)methyl)pyran-2-one
  参考文献：
  名称：

  Modification and biological evaluation of novel 4-hydroxy-pyrone derivatives as non-peptidic HIV-1 protease inhibitors

  摘要：

  In this study, we have modified 4-hydroxy-pyran-2-ones, especially introduced heteroatoms (S or O) into the substituents, and detected their interactions with the binding pockets of HIV-1 protease (PR). The results indicated that the ethoxyl groups at C-2' and C-5' of the phenyl ring could enhance the affinities to the S (1) ' and S (2) ' pockets and improve the inhibitory activities. The most potent compound 10f with an IC50 of 3.5 nM in enzymatic assay also exhibited good antiviral activity at the cellular level; it exhibited an EC50 value of 2.9 mu M in Simian immunodeficiency virus-infected CEM cells and suppressed the PR activity in 293T cells using western blot analysis.

  DOI：

  10.1007/s00044-010-9307-4
• 作为产物：
  描述：

  苯甲酰甲基苯基硫醚 在 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 2.5h， 生成 5-bromo-4-hydroxy-2-phenyl-2-(phenylsulfanylmethyl)-3H-pyran-6-one
  参考文献：
  名称：

  Modification and biological evaluation of novel 4-hydroxy-pyrone derivatives as non-peptidic HIV-1 protease inhibitors

  摘要：

  In this study, we have modified 4-hydroxy-pyran-2-ones, especially introduced heteroatoms (S or O) into the substituents, and detected their interactions with the binding pockets of HIV-1 protease (PR). The results indicated that the ethoxyl groups at C-2' and C-5' of the phenyl ring could enhance the affinities to the S (1) ' and S (2) ' pockets and improve the inhibitory activities. The most potent compound 10f with an IC50 of 3.5 nM in enzymatic assay also exhibited good antiviral activity at the cellular level; it exhibited an EC50 value of 2.9 mu M in Simian immunodeficiency virus-infected CEM cells and suppressed the PR activity in 293T cells using western blot analysis.

  DOI：

  10.1007/s00044-010-9307-4