4-(2-ethyl-4-oxopyrido[2,3-d]pyrimidin-4(3H)-yl)benzonitrile | 1005490-33-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 4-(2-ethyl-4-oxopyrido[2,3-d]pyrimidin-4(3H)-yl)benzonitrile
• 英文别名: 4-(2-Ethyl-4-oxopyrido[2,3-d]pyrimidin-3-yl)benzonitrile；4-(2-ethyl-4-oxopyrido[2,3-d]pyrimidin-3-yl)benzonitrile
• CAS: 1005490-33-4
• 化学式: C₁₆H₁₂N₄O
• 分子量: 276.297
• InChiKey: GPZLQIXHTBFMBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-ethyl-4-oxopyrido[2,3-d]pyrimidin-4(3H)-yl)benzonitrile 在 N-氯代丁二酰亚胺 、 溶剂黄146 作用下， 以99%的产率得到4-(2-(1-chloroethyl)-4-oxopyrido[2,3-d]pyrimidin-3(4H)-yl)benzonitrile
  参考文献：
  名称：

  Discovery of potent and specific CXCR3 antagonists

  摘要：

  The optimization of a series of 8-aza-quinazolinone analogs for antagonist activity against the CXCR3 receptor is reported. Compounds were optimized to avoid the formation of active metabolites and time-dependent- inhibitors of CYP3A4. In addition, antagonists showed potent against CXCR3 activity in whole blood and optimized to avoid activity in the chromosomal aberration assay. Compound 25 was identified as having the optimal balance of CXCR3 activity and pharmacokinetic properties across multiple pre-clinical species, which are reported herein. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.120
• 作为产物：
  描述：

  2-氨基烟酸 在 1,1'-双(二苯基膦)二茂铁 、 tris-(dibenzylideneacetone)dipalladium(0) 、 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(2-ethyl-4-oxopyrido[2,3-d]pyrimidin-4(3H)-yl)benzonitrile
  参考文献：
  名称：

  Discovery of potent and specific CXCR3 antagonists

  摘要：

  The optimization of a series of 8-aza-quinazolinone analogs for antagonist activity against the CXCR3 receptor is reported. Compounds were optimized to avoid the formation of active metabolites and time-dependent- inhibitors of CYP3A4. In addition, antagonists showed potent against CXCR3 activity in whole blood and optimized to avoid activity in the chromosomal aberration assay. Compound 25 was identified as having the optimal balance of CXCR3 activity and pharmacokinetic properties across multiple pre-clinical species, which are reported herein. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.120

文献信息

• Acetic Acid Mediated Coupling of 2-Aminonicotinamides with Ortho Esters: A Convenient, Scalable Synthesis of 2,3-Substituted Pyrido[2,3-<i>d</i>]pyrimidines
  作者：Johann Chan、Darin Gustin、Evan Divirgilio、Anil Guram、Margaret Faul

  DOI：10.1055/s-2007-990878

  日期：2007.12

  Substituted pyrido[2,3-d]pyrimidines are synthesized in good to excellent yields by treatment of various 2-aminonicotin­amides with triethyl orthopropionate or triethyl orthoacetate in the presence of acetic acid.

  以良好至优异的产率合成了取代的吡啶并[2,3-d]嘧啶，其方法是通过乙酸存在下，用各种2-氨基烟酰胺与三乙氧基丙烷或三乙氧基乙酸酯反应。
• [EN] ARYL NITRILE COMPOUNDS AND COMPOSITIONS AND THEIR USES IN TREATING INFLAMMATORY AND RELATED DISORDERS<br/>[FR] COMPOSES ET COMPOSITIONS D'ARYL NITRILE ET LEURS UTILISATIONS DANS LE TRAITEMENT DE MALADIES INFLAMMATOIRES ET DE TROUBLES ASSOCIES
  申请人：AMGEN INC

  公开号：WO2007002701A2

  公开（公告）日：2007-01-04

  [EN] Compounds, compositions and methods that are useful in the treatment of inflammatory and immune conditions and diseases are provided herein. In particular, the invention provides aryl nitrile compounds which modulate the expression and/or function of a chemokine receptor. The subject methods are useful for the treatment of inflammatory and immunoregulatory disorders and diseases, such as multiple sclerosis, rheumatoid arthritis, type I diabetes, asthma, psoriasis and inflammatory bowel disease.
  [FR] L'invention concerne des composés, des compositions et des procédés qui sont utilisés dans le traitement d'états et de maladies inflammatoires et immunes. En particulier, l'invention concerne des composés aryl nitrile qui modulent l'expression et/ou la fonction d'un récepteur de chimiokine. Les procédés selon l'invention sont utilisés pour le traitement de troubles et de maladies inflammatoires et immunorégulateurs tels que sclérose en plaques, polyarthrite rhumatoïde, diabète de type I, asthme, psoriasis et maladies intestinales inflammatoires.
• Discovery of potent and specific CXCR3 antagonists
  作者：Xiaoqi Chen、Jeff Mihalic、Jeff Deignan、Darin J. Gustin、Jason Duquette、Xiaohui Du、Johann Chan、Zice Fu、Michael Johnson、An-Rong Li、Kirk Henne、Tim Sullivan、Bryan Lemon、Ji Ma、Shichang Miao、George Tonn、Tassie Collins、Julio C. Medina

  DOI：10.1016/j.bmcl.2011.10.120

  日期：2012.1

  The optimization of a series of 8-aza-quinazolinone analogs for antagonist activity against the CXCR3 receptor is reported. Compounds were optimized to avoid the formation of active metabolites and time-dependent- inhibitors of CYP3A4. In addition, antagonists showed potent against CXCR3 activity in whole blood and optimized to avoid activity in the chromosomal aberration assay. Compound 25 was identified as having the optimal balance of CXCR3 activity and pharmacokinetic properties across multiple pre-clinical species, which are reported herein. (C) 2011 Elsevier Ltd. All rights reserved.