Acetic acid 2-methoxy-4-(4-phenyl-butyryl)-phenyl ester | 873296-39-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid 2-methoxy-4-(4-phenyl-butyryl)-phenyl ester
• 英文别名: [2-Methoxy-4-(4-phenylbutanoyl)phenyl] acetate
• CAS: 873296-39-0
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: RFFWBNRNWJDYEG-UHFFFAOYSA-N

物化性质

• 沸点：
  448.0±40.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Acetic acid 2-methoxy-4-(4-phenyl-butyryl)-phenyl ester 在 sodium hydroxide 、 乙酸酐 、 copper(II) nitrate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 1-(4-Hydroxy-3-methoxy-2-nitro-phenyl)-4-phenyl-butan-1-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Novel Series of “Ortho-Nitrated” Inhibitors of Catechol-O-methyltransferase

  摘要：

  Novel regioisomeric "ortho-nitrated" catechols related to the catechol-O-methyltransferase (COMT) inhibitors BIA 3-202 3 and BIA 3-335 4 were synthesized and biologically evaluated. Changing the position of the nitro group from the "classical" meta- to the ortho-position relative to the side-chain substituent of the nitrocatechol pharmacophore exerted profound effects on selectivity and duration of COMT inhibition. Alkylaryl compounds 7a-d possessed shorter duration of action than their regioisomers, but 7b displayed reversed selectivity over 3 at 3 and 6 h, exhibiting preferential central inhibition. In the amino-substituted series, ortho-nitrated regioisomer 14k was less peripherally selective than 4 and short-acting, whereas decahydroquinoline 14g displayed an unprecedented combination of long-acting and selective peripheral inhibition. 7b could provide a useful tool to probe the pharmacological utility of short-acting, centrally selective COMT inhibitors in the treatment of depression in Parkinsonian patients, and 14g represents a promising candidate for clinical evaluation as an adjunct to L-Dopa therapy.

  DOI：

  10.1021/jm0580454
• 作为产物：
  描述：

  乙酸酐 、 4'-hydroxy-3'-methoxy-4-phenylbutyrophenone 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 Acetic acid 2-methoxy-4-(4-phenyl-butyryl)-phenyl ester
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Novel Series of “Ortho-Nitrated” Inhibitors of Catechol-O-methyltransferase

  摘要：

  Novel regioisomeric "ortho-nitrated" catechols related to the catechol-O-methyltransferase (COMT) inhibitors BIA 3-202 3 and BIA 3-335 4 were synthesized and biologically evaluated. Changing the position of the nitro group from the "classical" meta- to the ortho-position relative to the side-chain substituent of the nitrocatechol pharmacophore exerted profound effects on selectivity and duration of COMT inhibition. Alkylaryl compounds 7a-d possessed shorter duration of action than their regioisomers, but 7b displayed reversed selectivity over 3 at 3 and 6 h, exhibiting preferential central inhibition. In the amino-substituted series, ortho-nitrated regioisomer 14k was less peripherally selective than 4 and short-acting, whereas decahydroquinoline 14g displayed an unprecedented combination of long-acting and selective peripheral inhibition. 7b could provide a useful tool to probe the pharmacological utility of short-acting, centrally selective COMT inhibitors in the treatment of depression in Parkinsonian patients, and 14g represents a promising candidate for clinical evaluation as an adjunct to L-Dopa therapy.

  DOI：

  10.1021/jm0580454