(5E)-4-amino-6-[1-(3-fluoro-benzyl)-1H-indol-5-ylamino]-pyrimidine-5-carbaldehyde | 1095314-12-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (5E)-4-amino-6-[1-(3-fluoro-benzyl)-1H-indol-5-ylamino]-pyrimidine-5-carbaldehyde
• 英文别名: 4-Amino-6-[[1-[(3-fluorophenyl)methyl]indol-5-yl]amino]pyrimidine-5-carbaldehyde；4-amino-6-[[1-[(3-fluorophenyl)methyl]indol-5-yl]amino]pyrimidine-5-carbaldehyde
• CAS: 1095314-12-7
• 化学式: C₂₀H₁₆FN₅O
• 分子量: 361.378
• InChiKey: AYAQSQPKQBJZQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  85.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (5E)-4-amino-6-[1-(3-fluoro-benzyl)-1H-indol-5-ylamino]-pyrimidine-5-carbaldehyde 、 甲氧基胺盐酸盐 以 甲醇 为溶剂， 生成 4-N-[1-[(3-fluorophenyl)methyl]indol-5-yl]-5-(methoxyiminomethyl)pyrimidine-4,6-diamine
  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
• 作为产物：
  描述：

  1-(3-fluorobenzyl)-1H-indol-5-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 (5E)-4-amino-6-[1-(3-fluoro-benzyl)-1H-indol-5-ylamino]-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

• Substituted Pyrimidinyl Oxime Kinase Inhibitors
  申请人：Battista Kathleen A.

  公开号：US20120157412A1

  公开（公告）日：2012-06-21

  The present invention is directed to substituted pyrimidine compounds of formula (I): and forms thereof, their synthesis and use for treating, preventing or ameliorating a chronic or acute protein kinase mediated disease, disorder or condition.

  本发明涉及式(I)的取代嘧啶化合物及其形式，它们的合成和用于治疗、预防或改善慢性或急性蛋白激酶介导的疾病、紊乱或状况的用途。
• US8367825B2
  申请人：——

  公开号：US8367825B2

  公开（公告）日：2013-02-05
• 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.