7-methoxy-3-phenyl-2-(1H-1,2,4-triazolyl-3-thio)-4H-1-benzopyran-4-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 7-methoxy-3-phenyl-2-(1H-1,2,4-triazolyl-3-thio)-4H-1-benzopyran-4-one
• 英文别名: 7-methoxy-3-phenyl-2-(1H-1,2,4-triazol-3-ylsulfanyl)-4H-chromen-4-one；7-methoxy-3-phenyl-2-(1H-1,2,4-triazol-5-ylsulfanyl)chromen-4-one
• 化学式: C₁₈H₁₃N₃O₃S
• 分子量: 351.386
• InChiKey: DUEZKGURISZNGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  7-methoxy-2-methylthio-3-phenyl-4H-1-benzopyran-4-one 在 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 7-methoxy-3-phenyl-2-(1H-1,2,4-triazolyl-3-thio)-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Synthesis and characterization of azole isoflavone inhibitors of aromatase

  摘要：

  The synthesis and biological evaluation of a series of 2-azole and 2-thioazole isoflavones as potential aromatase inhibitors are described. Differences in inhibitory activity of triazole and imidazole inhibitors are rationalized with density functional theory to expose a key difference in the electronic structure of these molecules. In addition, difference binding spectra of inhibitors to immuno-affinity-purified aromatase produces classical Type II spectra consistent with coordination of the nitrogen lone pair electrons to the aromatase P450 heme. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.03.050

文献信息

• Synthesis and characterization of azole isoflavone inhibitors of aromatase
  作者：John C Hackett、Young-Woo Kim、Bin Su、Robert W. Brueggemeier

  DOI：10.1016/j.bmc.2005.03.050

  日期：2005.6

  The synthesis and biological evaluation of a series of 2-azole and 2-thioazole isoflavones as potential aromatase inhibitors are described. Differences in inhibitory activity of triazole and imidazole inhibitors are rationalized with density functional theory to expose a key difference in the electronic structure of these molecules. In addition, difference binding spectra of inhibitors to immuno-affinity-purified aromatase produces classical Type II spectra consistent with coordination of the nitrogen lone pair electrons to the aromatase P450 heme. (c) 2005 Elsevier Ltd. All rights reserved.