7-(naphthalen-2-ylmethoxy)-3-phenyl-2-[(pyridin-4-ylmethyl)sulfanyl]-4H-chromen-4-one | 869801-00-3

• 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-(naphthalen-2-ylmethoxy)-3-phenyl-2-[(pyridin-4-ylmethyl)sulfanyl]-4H-chromen-4-one
• 英文别名: 7-(naphthalen-2-ylmethoxy)-3-phenyl-2-(pyridin-4-ylmethylsulfanyl)chromen-4-one
• CAS: 869801-00-3
• 化学式: C₃₂H₂₃NO₃S
• 分子量: 501.606
• InChiKey: IVKLCSXSBGHSJA-UHFFFAOYSA-N

物化性质

• 沸点：
  714.2±60.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  73.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2',4'-二羟基-2-苯基苯乙酮 在 sodium hydroxide 、 二甲基硫 、 偶氮二甲酸二异丙酯 、 三氟化硼乙醚 、 四丁基硫酸氢铵 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 7-(naphthalen-2-ylmethoxy)-3-phenyl-2-[(pyridin-4-ylmethyl)sulfanyl]-4H-chromen-4-one
  参考文献：
  名称：

  Lead optimization of 7-benzyloxy 2-(4′-pyridylmethyl)thio isoflavone aromatase inhibitors

  摘要：

  Aromatase, the enzyme responsible for estrogen biosynthesis, is a particularly attractive target in the treatment of hormone-dependent breast cancer. The synthesis and biological evaluation of a series of 2-(4'-pyridylmethyl)thio, 7-alkyl- or aryl-substituted isoflavones as potential aromatase inhibitors are described. The isoflavone derivatives demonstrate IC50 values from 79 to 553 nM and compete with the endogenous substrate, androstenedione. Data supporting the ability of these analogs to suppress aromatase enzyme activity in the SK-BR-3 breast cancer cell line are also presented. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2005.07.038

文献信息

• Lead optimization of 7-benzyloxy 2-(4′-pyridylmethyl)thio isoflavone aromatase inhibitors
  作者：Bin Su、John C Hackett、Edgar S. Díaz-Cruz、Young-Woo Kim、Robert W. Brueggemeier

  DOI：10.1016/j.bmc.2005.07.038

  日期：2005.12

  Aromatase, the enzyme responsible for estrogen biosynthesis, is a particularly attractive target in the treatment of hormone-dependent breast cancer. The synthesis and biological evaluation of a series of 2-(4'-pyridylmethyl)thio, 7-alkyl- or aryl-substituted isoflavones as potential aromatase inhibitors are described. The isoflavone derivatives demonstrate IC50 values from 79 to 553 nM and compete with the endogenous substrate, androstenedione. Data supporting the ability of these analogs to suppress aromatase enzyme activity in the SK-BR-3 breast cancer cell line are also presented. (c) 2005 Published by Elsevier Ltd.