2-chloro-6-dibromomethylquinoline | 791626-60-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-chloro-6-dibromomethylquinoline
• 英文别名: 2-Chloro-6-(dibromomethyl)quinoline
• CAS: 791626-60-3
• 化学式: C₁₀H₆Br₂ClN
• 分子量: 335.425
• InChiKey: PJBFLGKIWGMONY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-(溴甲基)-2-氯喹啉 、 2-chloro-6-dibromomethylquinoline 在 乌洛托品 、 盐酸 、 水 作用下， 以 乙醇 、 水 为溶剂， 反应 1.58h， 以92%的产率得到2-氯喹啉-6-甲醛
  参考文献：
  名称：

  WO2008/8912

  摘要：

  公开号：
• 作为产物：
  描述：

  2-氯-6-甲基喹啉 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 6-(溴甲基)-2-氯喹啉 、 2-chloro-6-dibromomethylquinoline
  参考文献：
  名称：

  Identification and Specificity Studies of Small-Molecule Ligands for SH3 Protein Domains

  摘要：

  The Src Homology 3 (SH3) domains are small protein-protein interaction domains that bind proline-rich sequences and mediate a wide range of cell-signaling and other important biological processes. Since deregulated signaling pathways form the basis of many human diseases, the SH3 domains have been attractive targets for novel therapeutics. High-affinity ligands for SH3 domains have been designed; however, these have all been peptide-based and no examples of entirely nonpeptide SH3 ligands have previously been reported. Using the mouse Tec Kinase SH3 domain as a model system for structure-based ligand design, we have identified several simple heterocyclic compounds that selectively bind to the Tec SH3 domain. Using a combination of nuclear magnetic resonance chemical shift perturbation, structure-activity relationships, and site-directed mutagenesis, the binding of these compounds at the proline-rich peptide-binding site has been characterized. The most potent of these, 2-aminoquinoline, bound with K-d = 125 muM and was able to compete for binding with a proline-rich peptide. Synthesis of 6-substitued-2-aminoquinolines resulted in ligands with up to 6-fold improved affinity over 2-aminoquinoline and enhanced specificity for the Tec SH3 domain. Therefore, 2-aminoquinolines may potentially be useful for the development of high affinity small molecule ligands for SH3 domains.

  DOI：

  10.1021/jm049533z

文献信息

• ANTIVIRAL AGENTS
  申请人：Schmitz Ulrich Franz

  公开号：US20080051384A1

  公开（公告）日：2008-02-28

  Disclosed are compounds and compositions of Formula (I) and their uses for treating Flaviviridae family virus infections.

  本发明涉及化合物和组合物的公式（I），以及它们用于治疗黄病毒科家族病毒感染的用途。
• [EN] ANTIVIRAL AGENTS<br/>[FR] AGENTS ANTIVIRAUX
  申请人：GENELABS TECH INC

  公开号：WO2008008907A2

  公开（公告）日：2008-01-17

  [EN] Disclosed are compounds and compositions of Formula (I) and their uses for treating Flaviviridae family virus infections.
  [FR] La présente invention concerne des composés et des compositions de formule (I) et leurs utilisations pour le traitement des infections par un virus de la famille des Flaviviridae.
• WO2008/8912
  申请人：——

  公开号：——

  公开（公告）日：——
• Identification and Specificity Studies of Small-Molecule Ligands for SH3 Protein Domains
  作者：Steven R. Inglis、Cvetan Stojkoski、Kim M. Branson、Jacquie F. Cawthray、Daniel Fritz、Emma Wiadrowski、Simon M. Pyke、Grant W. Booker

  DOI：10.1021/jm049533z

  日期：2004.10.1

  The Src Homology 3 (SH3) domains are small protein-protein interaction domains that bind proline-rich sequences and mediate a wide range of cell-signaling and other important biological processes. Since deregulated signaling pathways form the basis of many human diseases, the SH3 domains have been attractive targets for novel therapeutics. High-affinity ligands for SH3 domains have been designed; however, these have all been peptide-based and no examples of entirely nonpeptide SH3 ligands have previously been reported. Using the mouse Tec Kinase SH3 domain as a model system for structure-based ligand design, we have identified several simple heterocyclic compounds that selectively bind to the Tec SH3 domain. Using a combination of nuclear magnetic resonance chemical shift perturbation, structure-activity relationships, and site-directed mutagenesis, the binding of these compounds at the proline-rich peptide-binding site has been characterized. The most potent of these, 2-aminoquinoline, bound with K-d = 125 muM and was able to compete for binding with a proline-rich peptide. Synthesis of 6-substitued-2-aminoquinolines resulted in ligands with up to 6-fold improved affinity over 2-aminoquinoline and enhanced specificity for the Tec SH3 domain. Therefore, 2-aminoquinolines may potentially be useful for the development of high affinity small molecule ligands for SH3 domains.