3-(2-ethylphenylthio)-5,6-dihydro-4-hydroxy-6-((naphthalen-2-yloxy)methyl)-6-phenylpyran-2-one | 959425-58-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(2-ethylphenylthio)-5,6-dihydro-4-hydroxy-6-((naphthalen-2-yloxy)methyl)-6-phenylpyran-2-one
• 英文别名: 5-(2-ethylphenyl)sulfanyl-4-hydroxy-2-(naphthalen-2-yloxymethyl)-2-phenyl-3H-pyran-6-one
• CAS: 959425-58-2
• 化学式: C₃₀H₂₆O₄S
• 分子量: 482.6
• InChiKey: YHOLPUMDKAKKBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  81.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(萘-2-基氧基)-1-苯基乙酮 在 哌啶 、 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 作用下， 以 四氢呋喃 、 氯仿 、 叔丁醇 为溶剂， 反应 4.5h， 生成 3-(2-ethylphenylthio)-5,6-dihydro-4-hydroxy-6-((naphthalen-2-yloxy)methyl)-6-phenylpyran-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

文献信息

• Modification and biological evaluation of novel 4-hydroxy-pyrone derivatives as non-peptidic HIV-1 protease inhibitors
  作者：Meizi He、Ning Yang、Chunlai Sun、Xiaojian Yao、Ming Yang

  DOI：10.1007/s00044-010-9307-4

  日期：2011.3

  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.