6-Thiophen-2-ylquinoline-2,4-dicarboxylic acid | 1007237-54-8

• 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: 6-Thiophen-2-ylquinoline-2,4-dicarboxylic acid
• CAS: 1007237-54-8
• 化学式: C₁₅H₉NO₄S
• 分子量: 299.307
• InChiKey: ZSPMHBVQCJZHBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-Thiophen-2-ylquinoline-2,4-dicarboxylic acid 在 水 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 反应 16.0h， 生成 2-[2-(4-Hydroxyphenyl)ethylcarbamoyl]-6-thiophen-2-ylquinoline-4-carboxylic acid
  参考文献：
  名称：

  Modulating the interaction between CDK2 and cyclin A with a quinoline-based inhibitor

  摘要：

  A new class of quinoline-based kinase inhibitors has been discovered that both disrupt cyclin dependent 2 (CDK2) interaction with its cyclin A subunit and act as ATP competitive inhibitors. The key strategy for discovering this class of protein-protein disrupter compounds was to screen the monomer CDK2 in an affinity-selection/mass spectrometry-based technique and to perform secondary assays that identified compounds that bound only to the inactive CDK2 monomer and not the active CDK2/cyclin A heterodimer. Through a series of chemical modifications the affinity (Kd) of the original hit improved from 1 to 0.005μM.

  DOI：

  10.1016/j.bmcl.2013.11.041
• 作为产物：
  描述：

  5-溴靛红 在 potassium phosphate 、 palladium diacetate 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 生成 6-Thiophen-2-ylquinoline-2,4-dicarboxylic acid
  参考文献：
  名称：

  Modulating the interaction between CDK2 and cyclin A with a quinoline-based inhibitor

  摘要：

  A new class of quinoline-based kinase inhibitors has been discovered that both disrupt cyclin dependent 2 (CDK2) interaction with its cyclin A subunit and act as ATP competitive inhibitors. The key strategy for discovering this class of protein-protein disrupter compounds was to screen the monomer CDK2 in an affinity-selection/mass spectrometry-based technique and to perform secondary assays that identified compounds that bound only to the inactive CDK2 monomer and not the active CDK2/cyclin A heterodimer. Through a series of chemical modifications the affinity (Kd) of the original hit improved from 1 to 0.005μM.

  DOI：

  10.1016/j.bmcl.2013.11.041

文献信息

• Novel high affinity quinoline-based kinase ligands
  申请人：Deng Yongqi

  公开号：US20080045568A1

  公开（公告）日：2008-02-21

  Quinoline-based inhibitors of cyclin dependent kinase 2, compositions including the inhibitors, and methods of using the inhibitors and inhibitor compositions are described. The inhibitors and compositions including them are useful for treating disease or disease symptoms. The invention also provides for methods of making CDK-2 inhibitor compounds, methods of inhibiting CDK-2, and methods for treating disease or disease symptoms.

  基于喹啉的细胞周期蛋白依赖激酶2抑制剂，包括这些抑制剂的组合物，以及使用这些抑制剂和抑制剂组合物的方法。这些抑制剂和包括它们的组合物对治疗疾病或疾病症状有用。该发明还提供了制备CDK-2抑制剂化合物的方法，抑制CDK-2的方法，以及治疗疾病或疾病症状的方法。
• NOVEL HIGH AFFINITY QUINOLINE-BASED KINASE LIGANDS
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP1931657B1

  公开（公告）日：2013-12-25
• US7511063B2
  申请人：——

  公开号：US7511063B2

  公开（公告）日：2009-03-31
• [EN] NOVEL HIGH AFFINITY QUINOLINE-BASED KINASE LIGANDS<br/>[FR] NOUVEAUX LIGANDS DE KINASES A BASE DE QUINOLINE A AFFINITE ELEVEE
  申请人：SCHERING CORP

  公开号：WO2007022241A2

  公开（公告）日：2007-02-22

  [EN] Quinoline-based inhibitors of cyclin dependent kinase 2, compositions including the inhibitors, and methods of using the inhibitors and inhibitor compositions are described. The inhibitors and compositions including them are useful for treating disease or disease symptoms. The invention also provides for methods of making CDK-2 inhibitor compounds, methods of inhibiting CDK-2, and methods for treating disease or disease symptoms.
  [FR] L'invention concerne des inhibiteurs de la kinase 2 dépendant des cyclines à base de quinoline, des compositions comprenant ces inhibiteurs et des procédés d'utilisation des inhibiteurs et des compositions d'inhibiteurs. Ces inhibiteurs et les compositions comprenant ceux-ci sont utiles pour traiter une maladie ou des symptômes pathologiques. L'invention concerne aussi des procédés de fabrication de composés d'inhibiteurs de la CDK-2, de procédés d'inhibition de la CDK-2 et des méthodes de traitement d'une maladie ou de symptômes pathologiques.
• Modulating the interaction between CDK2 and cyclin A with a quinoline-based inhibitor
  作者：Yongqi Deng、Gerald W. Shipps、Lianyun Zhao、M. Arshad Siddiqui、Janeta Popovici-Muller、Patrick J. Curran、Jose S. Duca、Alan W. Hruza、Thierry O. Fischmann、Vincent S. Madison、Rumin Zhang、Charles W. McNemar、Todd W. Mayhood、Rosalinda Syto、Allen Annis、Paul Kirschmeier、Emma M. Lees、David A. Parry、William T. Windsor

  DOI：10.1016/j.bmcl.2013.11.041

  日期：2014.1

  A new class of quinoline-based kinase inhibitors has been discovered that both disrupt cyclin dependent 2 (CDK2) interaction with its cyclin A subunit and act as ATP competitive inhibitors. The key strategy for discovering this class of protein-protein disrupter compounds was to screen the monomer CDK2 in an affinity-selection/mass spectrometry-based technique and to perform secondary assays that identified compounds that bound only to the inactive CDK2 monomer and not the active CDK2/cyclin A heterodimer. Through a series of chemical modifications the affinity (Kd) of the original hit improved from 1 to 0.005μM.