Trifluoro-methanesulfonic acid 7-methoxy-3-(4-methoxy-phenyl)-4-oxo-3,4-dihydro-quinazolin-5-yl ester | 887468-56-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: Trifluoro-methanesulfonic acid 7-methoxy-3-(4-methoxy-phenyl)-4-oxo-3,4-dihydro-quinazolin-5-yl ester
• 英文别名: [7-Methoxy-3-(4-methoxyphenyl)-4-oxoquinazolin-5-yl] trifluoromethanesulfonate
• CAS: 887468-56-6
• 化学式: C₁₇H₁₃F₃N₂O₆S
• 分子量: 430.361
• InChiKey: CTPWMMUPYSIRAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid 7-methoxy-3-(4-methoxy-phenyl)-4-oxo-3,4-dihydro-quinazolin-5-yl ester 在 palladium diacetate 、 二苯基丙基膦 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 25.0h， 生成 5-(Hydroxymethyl)-7-methoxy-3-(4-methoxyphenyl)quinazolin-4-one
  参考文献：
  名称：

  WO2006/116401

  摘要：

  公开号：
• 作为产物：
  描述：

  1,2-dihydro-5,7-dimethoxy-3,1-benzoxazine-2,4-dione 在 4-二甲氨基吡啶 、 sodium hydride 、 lithium chloride 作用下， 以 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.5h， 生成 Trifluoro-methanesulfonic acid 7-methoxy-3-(4-methoxy-phenyl)-4-oxo-3,4-dihydro-quinazolin-5-yl ester
  参考文献：
  名称：

  Synthesis and Characterization of 3-Arylquinazolinone and 3-Arylquinazolinethione Derivatives as Selective Estrogen Receptor Beta Modulators

  摘要：

  On the basis of the stucture of genistein, a new series of 3-arylquinazolines was prepared and tested for their estrogen receptor (ER) alpha and beta affinities. 5,7-Dihydroxy-3 -(4-hydroxyphenyl)-4(3H)-quinazolinone (1aa) acts as an agonist on both ER subtypes. It has 62-fold higher binding affinity [IC50(ER beta) = 179 nM] and 38-fold higher functional potency in a transcription assay [EC50(ER beta) = 76 nM] with ER beta than with ER alpha, thus improving upon the selectivity of genistein. All of the analogues showed preferential binding affinity for ER. Many are also more potent in activating transcription by ER beta than by ER alpha. Transformation of the C=O functionality at position 4 into a C=S group provided 5,7-dihydroxy-3-(4-hydroxyphenyl)4(3H)-quinazolinethione (1ba), which acts as an agonist on both ER subtypes but has 56-fold higher binding affinity for ER beta over ER alpha [IC50(ER beta) = 47 nM] and 215-fold higher potency in the transcription assay [EC50(ER beta) = 13 nM]. These ER beta-selective compounds may represent valuable tools in understanding the differences in structure and biological function of ER beta and ER alpha.

  DOI：

  10.1021/jm0509389

文献信息

• US7456188B1
  申请人：——

  公开号：US7456188B1

  公开（公告）日：2008-11-25