N-[1-(3-bromophenyl)-3-naphthalen-2-yl-3-oxopropyl]acetamide | 1338705-45-5

• 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-(3-bromophenyl)-3-naphthalen-2-yl-3-oxopropyl]acetamide
• CAS: 1338705-45-5
• 化学式: C₂₁H₁₈BrNO₂
• 分子量: 396.283
• InChiKey: LDCVOUABGXBNQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  间溴苯甲醛 、 乙腈 、 2-萘乙酮 在 zinc perchlorate 、 乙酰氯 作用下， 以85%的产率得到N-[1-(3-bromophenyl)-3-naphthalen-2-yl-3-oxopropyl]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

• 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.