5-溴苯并[d]异噻唑-3-胺 | 613262-16-1

• 物质功能分类: 有机原料 - 氨基化合物 - 环烷胺、芳香单胺、芳香多胺及其衍生物和盐
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 5-溴苯并[d]异噻唑-3-胺
• 英文名称: 5-bromobenzo[d]isothiazol-3-amine
• 英文别名: 5-bromo-1,2-benzothiazol-3-amine
• CAS: 613262-16-1
• 化学式: C₇H₅BrN₂S
• 分子量: 229.1
• InChiKey: NTLSBZHEUNMUAP-UHFFFAOYSA-N

物化性质

• 沸点：
  279.3±22.0 °C(Predicted)
• 密度：
  1.836±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

制备方法与用途

5-溴苯并[D]异噻唑-3-胺可以作为有机合成中间体和医药中间体，主要应用于实验室研发及化工医药的生产过程中。

反应信息

• 作为反应物：
  描述：

  5-溴苯并[d]异噻唑-3-胺 在 四(三苯基膦)钯 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 乙二醇二甲醚 、 二氯甲烷 为溶剂， 生成 N-(5-(3,4-dimethoxyphenyl)benzo[d]isothiazol-3-yl)cyclohexanecarboxamide
  参考文献：
  名称：

  Discovery of Dual Death-Associated Protein Related Apoptosis Inducing Protein Kinase 1 and 2 Inhibitors by a Scaffold Hopping Approach

  摘要：

  DRAK2 emerged as a promising drug target for the treatment of autoimmune diseases and to prevent graft rejection after organ transplantation. Screening of a compound library in a DRAK2 binding assay led to the identification of an isothiazolo[5,4-b]pyridine derivative as a novel ligand for DRAK2, displaying a K-d value of 1.6 mu M. Subsequent medicinal chemistry work led to the discovery of a thieno[2,3-b]pyridine derivative with strong DRAK2 binding affinity (K-d = 9 nM). Moreover, this compound also behaves as a functional inhibitor of DRAK2 enzymatic activity, displaying an IC50 value of 0.82 mu M, although lacking selectivity, when tested against DRAK1. This paper describes for the first time functionally active dual DRAK1 and DRAK2 inhibitors that can be used as starting point for the synthesis of chemical tool compounds to study DRAK1 and DRAK2 biology, or they can be considered as hit compounds for hit-to-lead optimization campaigns in drug discovery programs.

  DOI：

  10.1021/jm5007929
• 作为产物：
  描述：

  5-bromo-2-mercaptobenzonitrile 在 ammonium hydroxide 、 sodium hypochlorite 、 sodium hydroxide 作用下， 反应 4.0h， 以51%的产率得到5-溴苯并[d]异噻唑-3-胺
  参考文献：
  名称：

  Discovery of Dual Death-Associated Protein Related Apoptosis Inducing Protein Kinase 1 and 2 Inhibitors by a Scaffold Hopping Approach

  摘要：

  DRAK2 emerged as a promising drug target for the treatment of autoimmune diseases and to prevent graft rejection after organ transplantation. Screening of a compound library in a DRAK2 binding assay led to the identification of an isothiazolo[5,4-b]pyridine derivative as a novel ligand for DRAK2, displaying a K-d value of 1.6 mu M. Subsequent medicinal chemistry work led to the discovery of a thieno[2,3-b]pyridine derivative with strong DRAK2 binding affinity (K-d = 9 nM). Moreover, this compound also behaves as a functional inhibitor of DRAK2 enzymatic activity, displaying an IC50 value of 0.82 mu M, although lacking selectivity, when tested against DRAK1. This paper describes for the first time functionally active dual DRAK1 and DRAK2 inhibitors that can be used as starting point for the synthesis of chemical tool compounds to study DRAK1 and DRAK2 biology, or they can be considered as hit compounds for hit-to-lead optimization campaigns in drug discovery programs.

  DOI：

  10.1021/jm5007929

文献信息

• [EN] BICYCLIC INHIBITORS OF ALK5 AND METHODS OF USE<br/>[FR] INHIBITEURS BICYCLIQUES DE L'ALK5 ET PROCÉDÉS D'UTILISATION
  申请人：THERAVANCE BIOPHARMA R&D IP LLC

  公开号：WO2022251359A1

  公开（公告）日：2022-12-01

  The present disclosure provides inhibitors of activin receptor-like kinase 5 (ALK5). Also disclosed are methods to modulate the activity of ALK5 and methods of treatment of disorders mediated by ALK5.

  本公开提供抑制活性素受体样激酶5（ALK5）的抑制剂。还公开了调节ALK5活性的方法以及治疗由ALK5介导的疾病的方法。