N-[1-(2,3,4-trimethoxyphenyl)-3-oxo-3-phenylpropyl]acetamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: N-[1-(2,3,4-trimethoxyphenyl)-3-oxo-3-phenylpropyl]acetamide
• 英文别名: N-[3-oxo-3-phenyl-1-(2,3,4-trimethoxyphenyl)propyl]acetamide
• 化学式: C₂₀H₂₃NO₅
• 分子量: 357.406
• InChiKey: DFTPOPZYKKPXPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯乙酮 、 乙腈 、 2,3,4-三甲氧基苯甲醛 在 zinc perchlorate 、 乙酰氯 作用下， 生成 N-[1-(2,3,4-trimethoxyphenyl)-3-oxo-3-phenylpropyl]acetamide
  参考文献：
  名称：

  N-(1,3-Diaryl-3-oxopropyl)amides as a new template for xanthine oxidase inhibitors

  摘要：

  A series of forty two N-(1,3-diaryl-3-oxopropyl)amides were synthesized via an efficient, modified Dakin-West reaction and were evaluated for in vitro xanthine oxidase inhibitory activity for the first time. Structure-activity relationship analyses have been presented. Selected active xanthine oxidase inhibitors (3r, 3s, and 3zh) were assessed in vivo to study their anti-hyperuricemic effect in potassium oxonate induced hyperuricemic mice model. Compound 3s emerged as the most potent xanthine oxidase inhibitor (IC50 = 2.45 mu M) as well as the most potent anti-hyperuricemic agent. The basis of significant inhibition of xanthine oxidase by 3s was rationalized by its molecular docking into catalytic site of xanthine oxidase. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.039

文献信息

• Efficient Synthesis of β‐Acetylamino Ketones using Silica‐Supported Sodium Hydrogen Sulfate as a Heterogeneous Catalyst
  作者：N. Vijaya Kumari、Lingaiah Nagarapu、Shivaraj

  DOI：10.1080/00397910701410467

  日期：2007.7

  Abstract Silica‐supported sodium hydrogen sulfate (NaHSO4 · SiO2) efficiently catalyzes the four‐component reaction of aryl aldehydes, enolisable ketones, acetyl chloride, and acetonitrile to form the corresponding β‐acetylamino ketones at room temperature. The catalyst is inexpensive and ecofriendly and works under heterogeneous conditions.The present methodology offers several advantages such as

  摘要 二氧化硅负载的硫酸氢钠 (NaHSO4·SiO2) 在室温下可有效催化芳醛、可烯化酮、乙酰氯和乙腈的四组分反应生成相应的 β-乙酰氨基酮。该催化剂价格低廉且环保，可在非均相条件下工作。本方法提供了几个优点，如产率高、程序简单、反应时间短（1-3 小时）和条件温和。
• N-(1,3-Diaryl-3-oxopropyl)amides as a new template for xanthine oxidase inhibitors
  作者：Kunal Nepali、Amit Agarwal、Sameer Sapra、Vineet Mittal、Raj Kumar、Uttam C. Banerjee、Manish K. Gupta、Naresh K. Satti、Om P. Suri、Kanaya L. Dhar

  DOI：10.1016/j.bmc.2011.07.039

  日期：2011.9

  A series of forty two N-(1,3-diaryl-3-oxopropyl)amides were synthesized via an efficient, modified Dakin-West reaction and were evaluated for in vitro xanthine oxidase inhibitory activity for the first time. Structure-activity relationship analyses have been presented. Selected active xanthine oxidase inhibitors (3r, 3s, and 3zh) were assessed in vivo to study their anti-hyperuricemic effect in potassium oxonate induced hyperuricemic mice model. Compound 3s emerged as the most potent xanthine oxidase inhibitor (IC50 = 2.45 mu M) as well as the most potent anti-hyperuricemic agent. The basis of significant inhibition of xanthine oxidase by 3s was rationalized by its molecular docking into catalytic site of xanthine oxidase. (C) 2011 Elsevier Ltd. All rights reserved.