2-[(3-Fluorophenyl)methyl]-1H-benzimidazol-6-amine | 833474-49-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-[(3-Fluorophenyl)methyl]-1H-benzimidazol-6-amine
• 英文别名: 2-[(3-fluorophenyl)methyl]-3H-benzimidazol-5-amine
• CAS: 833474-49-0
• 化学式: C₁₄H₁₂FN₃
• mdl: MFCD09939787
• 分子量: 241.268
• InChiKey: DAFQMQOYWQQNCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  54.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[(3-Fluorophenyl)methyl]-1H-benzimidazol-6-amine 、 4-氨基-6-氯-5-醛基嘧啶 在 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 生成 4-amino-6-[[2-[(3-fluorophenyl)methyl]-3H-benzimidazol-5-yl]amino]pyrimidine-5-carbaldehyde
  参考文献：
  名称：

  Discovery of novel 4-amino-6-arylaminopyrimidine-5-carbaldehyde oximes as dual inhibitors of EGFR and ErbB-2 protein tyrosine kinases

  摘要：

  We herein disclose a novel series of 4-aminopyrimidine-5-carbaldehyde oximes that are potent and selective inhibitors of both EGFR and ErbB-2 tyrosine kinases, with IC50 values in the nanomolar range. Structure-activity relationship (SAR) studies elucidated a critical role for the 4-amino and C-6 arylamino moieties. The X-ray co-crystal structure of EGFR with 37 was determined and validated our design rationale. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.024

文献信息

• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSES CHIMIQUES
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2005007083A2

  公开（公告）日：2005-01-27

  The present invention discloses thienopyrimidine derivatives, compositions and medicaments containing the same, as well as processes for the preparation and use of such compounds, compositions and medicaments. Such thienopyrimidine derivatives are useful in the treatment of diseases associated with inappropriate ErbB family kinase activity.
• Discovery of novel 4-amino-6-arylaminopyrimidine-5-carbaldehyde oximes as dual inhibitors of EGFR and ErbB-2 protein tyrosine kinases
  作者：Guozhang Xu、Lily Lee Searle、Terry V. Hughes、Amanda K. Beck、Peter J. Connolly、Marta C. Abad、Michael P. Neeper、Geoffrey T. Struble、Barry A. Springer、Stuart L. Emanuel、Robert H. Gruninger、Niranjan Pandey、Mary Adams、Sandra Moreno-Mazza、Angel R. Fuentes-Pesquera、Steven A. Middleton、Lee M. Greenberger

  DOI：10.1016/j.bmcl.2008.05.024

  日期：2008.6

  We herein disclose a novel series of 4-aminopyrimidine-5-carbaldehyde oximes that are potent and selective inhibitors of both EGFR and ErbB-2 tyrosine kinases, with IC50 values in the nanomolar range. Structure-activity relationship (SAR) studies elucidated a critical role for the 4-amino and C-6 arylamino moieties. The X-ray co-crystal structure of EGFR with 37 was determined and validated our design rationale. (C) 2008 Elsevier Ltd. All rights reserved.