(R)-N-(1-(3-(4-ethoxyphenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)ethyl)-2-(4-(methylsulfonyl)phenyl)-N-(pyridin-3-ylmethyl)acetamide | 1191255-38-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (R)-N-(1-(3-(4-ethoxyphenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)ethyl)-2-(4-(methylsulfonyl)phenyl)-N-(pyridin-3-ylmethyl)acetamide
• 英文别名: N-[(1R)-1-[3-(4-ethoxyphenyl)-4-oxoquinazolin-2-yl]ethyl]-2-(4-methylsulfonylphenyl)-N-(pyridin-3-ylmethyl)acetamide
• CAS: 1191255-38-5
• 化学式: C₃₃H₃₂N₄O₅S
• 分子量: 596.707
• InChiKey: HMVZNFVEZACBSL-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (R)-3-(4-ethoxyphenyl)-2-(1-((pyridin-3-ylmethyl)amino)ethyl)quinazolin-4(3H)-one 、 4-甲烷磺酰基苯乙酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (R)-N-(1-(3-(4-ethoxyphenyl)-4-oxo-3,4-dihydroquinazolin-2-yl)ethyl)-2-(4-(methylsulfonyl)phenyl)-N-(pyridin-3-ylmethyl)acetamide
  参考文献：
  名称：

  Optimization of a series of quinazolinone-derived antagonists of CXCR3

  摘要：

  The evaluation of the CXCR3 antagonist AMG 487 in clinic trials was complicated due to the formation of an active metabolite. In this Letter, we will discuss the further optimization of the quinazolinone series that led to the discovery of compounds devoid of the formation of the active metabolite that was seen with AMG 487. In addition, these compounds also feature increased potency and good pharmacokinetic properties. We will also discuss the efficacy of the lead compound 34 in a mouse model of cellular recruitment induced by bleomycin. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.032

文献信息

• Optimization of a series of quinazolinone-derived antagonists of CXCR3
  作者：Jiwen Liu、Zice Fu、An-Rong Li、Michael Johnson、Liusheng Zhu、Andrew Marcus、Jay Danao、Tim Sullivan、George Tonn、Tassie Collins、Julio Medina

  DOI：10.1016/j.bmcl.2009.07.032

  日期：2009.9

  The evaluation of the CXCR3 antagonist AMG 487 in clinic trials was complicated due to the formation of an active metabolite. In this Letter, we will discuss the further optimization of the quinazolinone series that led to the discovery of compounds devoid of the formation of the active metabolite that was seen with AMG 487. In addition, these compounds also feature increased potency and good pharmacokinetic properties. We will also discuss the efficacy of the lead compound 34 in a mouse model of cellular recruitment induced by bleomycin. (C) 2009 Elsevier Ltd. All rights reserved.