| 1549643-27-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1549643-27-7
• 化学式: C₁₁H₉BrN₂O₃
• 分子量: 297.108
• InChiKey: QOUXBLHNOAILPE-UHFFFAOYSA-N

物化性质

• 沸点：
  425.6±48.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  61.19
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 盐酸 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 copper(l) iodide 、 四(三苯基膦)钯 、 氨 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 47.0h， 生成 tert-butyl (5-bromo-3-(4-hydroxybut-1-yn-1-yl)-1H-indazole-7-carbonyl)carbamate
  参考文献：
  名称：

  Linear propargylic alcohol functionality attached to the indazole-7-carboxamide as a JAK1-specific linear probe group

  摘要：

  Selective inhibition of JAK1 has recently been proposed as an appropriate therapeutic rationale for the treatment of inflammatory diseases such as rheumatoid arthritis (RA). In this study, through pairwise comparison and 3D alignment of the JAK isozyme structures bound to the same inhibitor molecule, we reasoned that an alkynol functionality would serve as an isozyme-specific probe group, which would enable the resulting inhibitor to differentiate the ATP-binding site of JAK1 from those of other isozymes. The 3-alkynolyl-5-(4'-indazolyl) indazole-7-carboxamide derivatives were thus prepared, and in vitro evaluation of their inhibitory activity against the JAK isozymes revealed that the propargyl alcohol functionality endowed the 5-(4'-indazolyl) indazole-7-carboxamide scaffold with JAK1 selectivity over other JAK isozymes, particularly JAK2. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.033
• 作为产物：
  描述：

  2-氨基-3-甲基苯甲酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 potassium acetate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.25h， 生成
  参考文献：
  名称：

  Linear propargylic alcohol functionality attached to the indazole-7-carboxamide as a JAK1-specific linear probe group

  摘要：

  Selective inhibition of JAK1 has recently been proposed as an appropriate therapeutic rationale for the treatment of inflammatory diseases such as rheumatoid arthritis (RA). In this study, through pairwise comparison and 3D alignment of the JAK isozyme structures bound to the same inhibitor molecule, we reasoned that an alkynol functionality would serve as an isozyme-specific probe group, which would enable the resulting inhibitor to differentiate the ATP-binding site of JAK1 from those of other isozymes. The 3-alkynolyl-5-(4'-indazolyl) indazole-7-carboxamide derivatives were thus prepared, and in vitro evaluation of their inhibitory activity against the JAK isozymes revealed that the propargyl alcohol functionality endowed the 5-(4'-indazolyl) indazole-7-carboxamide scaffold with JAK1 selectivity over other JAK isozymes, particularly JAK2. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.033

文献信息

• 야누스 키나아제 1 (Janus kinase 1)의 활성을 선택적으로 저해하는 인다졸 유도체
  申请人：Konkuk University Industrial Cooperation Corp 건국대학교 산학협력단(220040157648) BRN ▼206-82-07325

  公开号：KR101551187B1

  公开（公告）日：2015-09-08

  본 발명은 야누스 키나아제 1 (Janus Kinase 1)의 활성을 선택적으로 저해하는 활성을 갖는 인다졸 유도체 및 그 화합물의 류마티스성 관절염 치료제로서의 용도에 관한 것이다.

  这项发明涉及具有选择性抑制Janus Kinase 1（JAK1）活性的吲唑诱导体及其化合物的用途作为类风湿性关节炎的治疗剂。