2,2-dimethyl-propanoic acid 3,4-dihydro-3-(3-methoxyphenyl)-4-oxo-2H-1-benzopyran-7-yl ester | 738601-28-0

• 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: 2,2-dimethyl-propanoic acid 3,4-dihydro-3-(3-methoxyphenyl)-4-oxo-2H-1-benzopyran-7-yl ester
• CAS: 738601-28-0
• 化学式: C₂₁H₂₂O₅
• 分子量: 354.403
• InChiKey: DZELPVIJKKWHJU-UHFFFAOYSA-N

物化性质

• 沸点：
  511.9±50.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-propanoic acid 3,4-dihydro-3-(3-methoxyphenyl)-4-oxo-2H-1-benzopyran-7-yl ester 、 4-苄氧基氯化苄 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 以32%的产率得到2,2-dimethyl-propanoic acid 3,4-dihydro-4-hydroxy-3-(3-methoxyphenyl)-4-[[4-(phenylmethoxy)phenyl]methyl]-2H-1-benzopyran-7-yl ester
  参考文献：
  名称：

  Synthesis, pharmacological evaluation, and structure–activity relationships of benzopyran derivatives with potent SERM activity

  摘要：

  The synthesis, binding affinity for estrogen receptor subtypes (ERalpha and ERbeta) and pharmacological activity on rat uterus of a new class of potent ligands, characterized by a 3-phenylbenzopyran scaffold with a basic side chain in position 4, are reported. Some of these compounds, endowed with very high receptor affinity, showed potent inhibition of agonist-stimulated uterine growth, with no or limited proliferative effect. Binding affinity mostly depended on the nature and position of substituents at the 3-phenyl ring, while the uterine activity seems to be affected by basic chain length. Compound 9c (CHF4227) showed excellent binding affinity and antagonist activity on the uterus. The docking of benzopyran derivatives explained the structure-affinity relationships observed for 3-phenyl substitution: a small, hydrophobic 4'-substituent could interact with a small accessory binding cavity, while di-substitution at 4' and 3' led to some ERalpha selectivity. This selectivity can be ascribed to differences in amino acid composition and side chain conformation in the region accommodating the 3-phenyl ring at human ERalpha and ERbeta ligand-binding domain. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.015
• 作为产物：
  描述：

  三甲基乙酰氯 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 水 、 丙酮 、 乙腈 为溶剂， 20.0 ℃ 、206.84 kPa 条件下， 生成 2,2-dimethyl-propanoic acid 3,4-dihydro-3-(3-methoxyphenyl)-4-oxo-2H-1-benzopyran-7-yl ester
  参考文献：
  名称：

  Synthesis, pharmacological evaluation, and structure–activity relationships of benzopyran derivatives with potent SERM activity

  摘要：

  The synthesis, binding affinity for estrogen receptor subtypes (ERalpha and ERbeta) and pharmacological activity on rat uterus of a new class of potent ligands, characterized by a 3-phenylbenzopyran scaffold with a basic side chain in position 4, are reported. Some of these compounds, endowed with very high receptor affinity, showed potent inhibition of agonist-stimulated uterine growth, with no or limited proliferative effect. Binding affinity mostly depended on the nature and position of substituents at the 3-phenyl ring, while the uterine activity seems to be affected by basic chain length. Compound 9c (CHF4227) showed excellent binding affinity and antagonist activity on the uterus. The docking of benzopyran derivatives explained the structure-affinity relationships observed for 3-phenyl substitution: a small, hydrophobic 4'-substituent could interact with a small accessory binding cavity, while di-substitution at 4' and 3' led to some ERalpha selectivity. This selectivity can be ascribed to differences in amino acid composition and side chain conformation in the region accommodating the 3-phenyl ring at human ERalpha and ERbeta ligand-binding domain. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.05.015