4-(3-(1,3-dioxoisoindolin-2-yl)-2-hydroxypropylamino)benzonitrile | 1261131-68-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 4-(3-(1,3-dioxoisoindolin-2-yl)-2-hydroxypropylamino)benzonitrile
• 英文别名: 4-[[(2R)-3-(1,3-dioxoisoindol-2-yl)-2-hydroxypropyl]amino]benzonitrile
• CAS: 1261131-68-3
• 化学式: C₁₈H₁₅N₃O₃
• 分子量: 321.335
• InChiKey: CPGXZLKEQPMDCY-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  93.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(3-(1,3-dioxoisoindolin-2-yl)-2-hydroxypropylamino)benzonitrile 在 4-二甲氨基吡啶 盐酸 、 4-羟基苯并三唑 、 一水合肼 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 77.0h， 生成 (S)-5-chloro-N-((3-(4-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)thiophene-2-carboxamide
  参考文献：
  名称：

  [EN] METHOD FOR PREPARING (S)-5-CHLORO-N-((3-(4-(5,6-DIHYDRO-4H-1,2,4-OXADIAZIN-3-YL)PHENYL)-2-OXOOXAZOLIDIN-5-YL)METHYL)THIOPHENE-2-CARBOXAMIDE DERIVATIVES
  [FR] PROCÉDÉ D'ÉLABORATION DE DÉRIVÉS DE (S)-5-CHLORO-N-((3-(4-(5,6-DIHYDRO-4H-1,2,4-OXADIAZIN-3-YL)PHÉNYL)-2-OXOOXAZOLIDIN-5-YL)MÉTHYL)THIOPHÈNE-2-CARBOXAMIDE

  摘要：

  公开号：

  WO2011005028A3
• 作为产物：
  描述：

  (S)-N-缩水甘油邻苯二甲酰亚胺 、 对氨基苯腈 反应 13.0h， 以84%的产率得到4-(3-(1,3-dioxoisoindolin-2-yl)-2-hydroxypropylamino)benzonitrile
  参考文献：
  名称：

  [EN] METHOD FOR PREPARING (S)-5-CHLORO-N-((3-(4-(5,6-DIHYDRO-4H-1,2,4-OXADIAZIN-3-YL)PHENYL)-2-OXOOXAZOLIDIN-5-YL)METHYL)THIOPHENE-2-CARBOXAMIDE DERIVATIVES
  [FR] PROCÉDÉ D'ÉLABORATION DE DÉRIVÉS DE (S)-5-CHLORO-N-((3-(4-(5,6-DIHYDRO-4H-1,2,4-OXADIAZIN-3-YL)PHÉNYL)-2-OXOOXAZOLIDIN-5-YL)MÉTHYL)THIOPHÈNE-2-CARBOXAMIDE

  摘要：

  公开号：

  WO2011005028A3

文献信息

• Design, synthesis and structure–activity relationship of oxazolidinone derivatives containing novel S4 ligand as FXa inhibitors
  作者：Yanfang Zhao、Mingyan Jiang、Shunguang Zhou、Shasha Wu、Xiaolong Zhang、Longsheng Ma、Kai Zhang、Ping Gong

  DOI：10.1016/j.ejmech.2015.04.025

  日期：2015.5

  A novel series of potent and efficacious factor Xa inhibitors which possesses pyrrole/indole/thiazole moieties as S4 binding element was identified. Compound 7b showed strong human factor Xa inhibitory activity (IC50 = 2.01 nM) and anticoagulant activities in both human (PTCT2 = 0.15 mu M, APPTCT(2) = 0.30 mu M) and rabbit plasma (PTCT2 = 0.46 mu M, APPTCT(2) = 0.75 mu M). The SARs analyses indicated that the size and water solubility of different alkylamino group at the position of S4 ligand were responsible for the anticoagulant activity. (C) 2015 Elsevier Masson SAS. All rights reserved.
• METHOD FOR PREPARING (S)-5-CHLORO-N-((3-(4-(5,6-DIHYDRO-4H-1,2,4-OXADIAZIN-3-YL)PHENYL)-2-OXOOXAZOLIDIN-5-YL)METHYL)THIOPHENE-2-CARBOXAMIDE DERIVATIVES
  申请人：Cho Young Lag

  公开号：US20120108808A1

  公开（公告）日：2012-05-03

  Provided is a method for preparing (S)-5-chloro-N-((3-(4-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)thiophene-2-carboxamide derivatives of Formula (I) which are useful as blood coagulation factor Xa inhibitors, and said method using 1-fluoro-4-nitrobenzen as a starting material. According to the method of the present invention, (S)-5-chloro-N-((3-(4-(5,6-dihydro-4H-1,2,4-oxadiazin-3-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)thiophene-2-carboxamide derivatives of Formula (I) which are useful as blood coagulation factor Xa inhibitors can be prepared in a high purity and a high yield.
• US8637667B2
  申请人：——

  公开号：US8637667B2

  公开（公告）日：2014-01-28