N-benzyl-6-phenylfuro[2,3-d]pyrimidin-4-amine | 1209001-74-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃[2,3-d]嘧啶
• 英文名称: N-benzyl-6-phenylfuro[2,3-d]pyrimidin-4-amine
• CAS: 1209001-74-0
• 化学式: C₁₉H₁₅N₃O
• 分子量: 301.348
• InChiKey: OAYPHBWWZGQZHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  51
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基-5-苯基-3-呋喃甲腈 在 甲酸 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 30.0h， 生成 N-benzyl-6-phenylfuro[2,3-d]pyrimidin-4-amine
  参考文献：
  名称：

  Chiral 6-aryl-furo[2,3-d]pyrimidin-4-amines as EGFR inhibitors

  摘要：

  Epidermal growth factor receptor inhibitors are of importance in cancer therapy and possibly in the management of pain. Herein, we report a structure-activity relationship study with 29 new 6-aryl-furo [2,3-d]pyrimidin-4-amines, involving modification of the 4-amino group and 6-aryl function. The EGFR activity was especially dependent on having a chiral 4-benzylamino group with correct stereochemistry. Molecular dynamics indicate this to be due to favourable cation-pi interactions. The most active inhibitor identified, equipotent to Erlotinib, was substituted with (R)-1-phenylethylamine at C-4 and a N-1, N-1-dimethyl-1,2-diamine group in para position of the 6-aryl moiety. These new furopyrimidines had a different off-target kinase profile when compared to Erlotinib, and also possessed high activity towards Ba/F3 EGFR(L858R) reporter cells. Further, comparing the EGFR data of the furo[2,3-d]pyrimidin-4-amines with that of the corresponding thieno- and pyrrolopyrimidines concludes the furopyrimidine scaffold to be highly useful for development of new epidermal growth factor receptor antagonists. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.04.054

文献信息

• Efficient and library-friendly synthesis of furo- and thieno[2,3-d] pyrimidin-4-amine derivatives by microwave irradiation
  作者：Ying Han、Katalin Ebinger、Lauren E. Vandevier、Jennifer W. Maloney、David S. Nirschl、Harold N. Weller

  DOI：10.1016/j.tetlet.2009.11.071

  日期：2010.1

  A new, divergent, efficient, and selective synthesis of furo- and thieno[2,3-d]pyrimidin-4-amine derivatives by microwave irradiation has been developed starting from readily available amines and substituted 2-aminofuran-3-carbonitrile or 2-aminothiophene-3-carbonitrile, which are converted into corresponding formamidines in DMF using benzenesulfonyl chloride.

  从容易获得的胺和取代的2-氨基呋喃-3-甲腈或2-氨基化合物开始，开发了一种新的，发散的，有效的，选择性的微波辐射合成呋喃并和噻吩并[2,3 - d ]嘧啶-4-胺的衍生物。 -氨基噻吩-3-腈，其在DMF中使用苯磺酰氯转化为相应的甲am。