N4-(7-iodo-1H-indazol-5-yl)pyrimidine-2,4-diamine | 953411-13-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: N4-(7-iodo-1H-indazol-5-yl)pyrimidine-2,4-diamine
• 英文别名: 4-N-(7-iodo-1H-indazol-5-yl)pyrimidine-2,4-diamine
• CAS: 953411-13-7
• 化学式: C₁₁H₉IN₆
• 分子量: 352.137
• InChiKey: FOIYZNZAROTCFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.5
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  苯并噻吩-2-硼酸 、 N4-(7-iodo-1H-indazol-5-yl)pyrimidine-2,4-diamine 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以43%的产率得到N4-(7-(benzo[b]thiophen-2-yl)-1H-indazol-5-yl)pyrimidine-2,4-diamine
  参考文献：
  名称：

  2,4-Diaminopyrimidine MK2 inhibitors. Part II: Structure-based inhibitor optimization

  摘要：

  We describe structure-based optimization of a series of novel 2,4-diaminopyrimidine MK2 inhibitors. Co-crystal structures (see accompanying Letter) demonstrated a unique inhibitor binding mode. Resulting inhibitors had IC50 values as low as 19 nM and moderate selectivity against a kinase panel. Compounds 15, 31a, and 31b inhibit TNF alpha production in peripheral human monocytes. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.103
• 作为产物：
  描述：

  7-Iodo-1H-indazol-5-amine 、 2-氨基-4-氯嘧啶 以 乙醇 为溶剂， 反应 2.5h， 以91%的产率得到N4-(7-iodo-1H-indazol-5-yl)pyrimidine-2,4-diamine
  参考文献：
  名称：

  2,4-Diaminopyrimidine MK2 inhibitors. Part II: Structure-based inhibitor optimization

  摘要：

  We describe structure-based optimization of a series of novel 2,4-diaminopyrimidine MK2 inhibitors. Co-crystal structures (see accompanying Letter) demonstrated a unique inhibitor binding mode. Resulting inhibitors had IC50 values as low as 19 nM and moderate selectivity against a kinase panel. Compounds 15, 31a, and 31b inhibit TNF alpha production in peripheral human monocytes. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.103

文献信息

• Indazole compounds
  申请人：Ericsson M. Anna

  公开号：US20070282101A1

  公开（公告）日：2007-12-06

  Novel compounds of Formula (I) or pharmaceutically acceptable salts, prodrugs and biologically active metabolites thereof of Formula (I) wherein the substituents are as defined herein, which are useful as therapeutic agents.

  本发明提供了化合物(I)或其药学上可接受的盐、前药和生物活性代谢物，其中取代基如定义所述，这些化合物可用作治疗剂。
• Indazole Compounds
  申请人：Ericson Anna M.

  公开号：US20120053345A1

  公开（公告）日：2012-03-01

  Novel compounds of Formula (I) or pharmaceutically acceptable salts, prodrugs and biologically active metabolites thereof of Formula (I) wherein the substituents are as defined herein, which are useful as therapeutic agents.

  本发明涉及化合物(I)或其药学上可接受的盐、前药和生物活性代谢物，其中取代基的定义如本文所述，这些化合物可用作治疗剂。
• US8008481B2
  申请人：——

  公开号：US8008481B2

  公开（公告）日：2011-08-30
• 2,4-Diaminopyrimidine MK2 inhibitors. Part II: Structure-based inhibitor optimization
  作者：Christopher M. Harris、Anna M. Ericsson、Maria A. Argiriadi、Claude Barberis、David W. Borhani、Andrew Burchat、David J. Calderwood、George A. Cunha、Richard W. Dixon、Kristine E. Frank、Eric F. Johnson、Joanne Kamens、Silvia Kwak、Biqin Li、Kelly D. Mullen、Denise C. Perron、Lu Wang、Neil Wishart、Xiaoyun Wu、Xiaolei Zhang、Tami R. Zmetra、Robert V. Talanian

  DOI：10.1016/j.bmcl.2009.10.103

  日期：2010.1

  We describe structure-based optimization of a series of novel 2,4-diaminopyrimidine MK2 inhibitors. Co-crystal structures (see accompanying Letter) demonstrated a unique inhibitor binding mode. Resulting inhibitors had IC50 values as low as 19 nM and moderate selectivity against a kinase panel. Compounds 15, 31a, and 31b inhibit TNF alpha production in peripheral human monocytes. (c) 2009 Elsevier Ltd. All rights reserved.