2,2-dimethyl-propanoic acid 3-(3,4-dimethoxyphenyl)-4-oxo-4H-1-benzopyran-7-yl ester

• 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-(3,4-dimethoxyphenyl)-4-oxo-4H-1-benzopyran-7-yl ester
• 英文别名: 3-(3,4-dimethoxyphenyl)-4-oxo-4H-chromen-7-yl pivalate；[3-(3,4-dimethoxyphenyl)-4-oxochromen-7-yl] 2,2-dimethylpropanoate
• 化学式: C₂₂H₂₂O₆
• 分子量: 382.413
• InChiKey: UJGCZIIQFAJMJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-propanoic acid 3-(3,4-dimethoxyphenyl)-4-oxo-4H-1-benzopyran-7-yl ester 在 palladium on activated charcoal 氢气 作用下， 以 水 、 丙酮 为溶剂， 20.0 ℃ 、206.84 kPa 条件下， 生成 2,2-dimethyl-propanoic acid 3-(3,4-dimethoxyphenyl)-3,4-dihydro-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
• 作为产物：
  描述：

  3',4'-二甲氧基-7-羟基异黄酮 、 三甲基乙酰氯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 2,2-dimethyl-propanoic acid 3-(3,4-dimethoxyphenyl)-4-oxo-4H-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

文献信息

• Synthesis, pharmacological evaluation, and structure–activity relationships of benzopyran derivatives with potent SERM activity
  作者：Gabriele Amari、Elisabetta Armani、Silvia Ghirardi、Maurizio Delcanale、Maurizio Civelli、Paola Lorenza Caruso、Elisabetta Galbiati、Milco Lipreri、Silvia Rivara、Alessio Lodola、Marco Mor

  DOI：10.1016/j.bmc.2004.05.015

  日期：2004.7

  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.