Methyl 5-[(3-chloro-4-fluorophenyl)amino]pyrimido[4,5-c]quinoline-8-carboxylate | 1009821-08-2

• 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: Methyl 5-[(3-chloro-4-fluorophenyl)amino]pyrimido[4,5-c]quinoline-8-carboxylate
• 英文别名: methyl 5-(3-chloro-4-fluoroanilino)pyrimido[4,5-c]quinoline-8-carboxylate
• CAS: 1009821-08-2
• 化学式: C₁₉H₁₂ClFN₄O₂
• 分子量: 382.781
• InChiKey: XJYPFCRZPRXEHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  77
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Methyl 5-[(3-chloro-4-fluorophenyl)amino]pyrimido[4,5-c]quinoline-8-carboxylate 在 四甲基氢氧化铵 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 5-((3-chloro-4-fluorophenyl)amino)pyrimido[4,5-c]quinoline-8-carboxylic acid
  参考文献：
  名称：

  发现一种有效且选择性的基于萘啶的酪蛋白激酶 2 化学探针

  摘要：

  合成了基于萘啶的抑制剂，以产生酪蛋白激酶 2 (CK2) 的有效且具有细胞活性的抑制剂。当广泛分析时，化合物2选择性抑制 CK2α 和 CK2α'，从而使其成为 CK2 的精确选择性化学探针。在结构研究的基础上设计了结构相关但缺乏关键铰链结合氮的阴性对照（7 ）。化合物7不结合细胞中的 CK2α 或 CK2α'，并表现出优异的全激酶组选择性。当化合物2与结构不同的 CK2 化学探针：SGC-CK2-1 一起进行分析时，观察到了不同的抗癌活性。这种基于萘啶的化学探针 ( 2 ) 代表了用于研究 CK2 介导的生物学的最佳可用小分子工具之一。

  DOI：

  10.1021/acsmedchemlett.2c00530
• 作为产物：
  描述：

  5-溴-4-嘧啶甲酸甲酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 caesium carbonate 、 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 N-甲基吡咯烷酮 、 甲苯 为溶剂， 生成 Methyl 5-[(3-chloro-4-fluorophenyl)amino]pyrimido[4,5-c]quinoline-8-carboxylate
  参考文献：
  名称：

  Novel potent pyrimido[4,5-c]quinoline inhibitors of protein kinase CK2: SAR and preliminary assessment of their analgesic and anti-viral properties

  摘要：

  We describe the discovery of novel potent substituted pyrimido[4,5-c]quinoline ATP-competitive inhibitors of protein kinase CK2. A binding model of the inhibitors with the protein was elaborated on the basis of SAR and revealed various modes of interaction with the hinge region. Representative analog 14k (CK2 IC50 = 9 nM) showed anti-viral activity at nanomolar concentrations against HIV-1. Orally available compound 7e (CK2 IC50 = 3 nM) reduced pain in the phase II of a murine formalin model. These preliminary data confirm that properly optimized CK2 inhibitors may be used for anti-viral and pain therapy. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.091

文献信息

• PROTEIN KINASE MODULATORS
  申请人：CHUA Peter C.

  公开号：US20090239859A1

  公开（公告）日：2009-09-24

  The invention relates in part to molecules having certain biological activities that include, but are not limited to, inhibiting cell proliferation, modulating protein kinase activity and modulating polymerase activity. Molecules of the invention can modulate Pim kinase activity and/or FMS-like tyrosine kinase (Flt) activity. The invention also relates in part to methods for using such molecules.

  该发明部分涉及具有特定生物活性的分子，包括但不限于抑制细胞增殖、调节蛋白激酶活性和调节聚合酶活性。该发明的分子可以调节Pim激酶活性和/或FMS样酪氨酸激酶（Flt）活性。该发明还涉及使用这些分子的方法。
• SERINE-THREONINE PROTEIN KINASE AND PARP MODULATORS
  申请人：CHUA Peter

  公开号：US20090264423A2

  公开（公告）日：2009-10-22

  The invention relates in part to molecules having certain biological activities that include, but are not limited to, inhibiting cell proliferation, modulating protein kinase activity and modulating polymerase activity. Molecules of the invention can modulate casein kinase (CK) activity and/or poly(ADP-ribose)polymerase (PARP) activity. The invention also relates in part to methods for using such molecules.

  本发明涉及具有某些生物活性的分子，包括但不限于抑制细胞增殖、调节蛋白激酶活性和调节聚合酶活性。本发明的分子可以调节酪蛋白激酶（CK）活性和/或聚(ADP-核糖)聚合酶（PARP）活性。本发明还涉及使用这些分子的方法。
• FUSED TRICYCLIC COMPOUNDS AS SERINE-THREONINE PROTEIN KINASE AND PARP MODULATORS
  申请人：CHUA Peter C.

  公开号：US20110263581A1

  公开（公告）日：2011-10-27

  The invention relates in part to molecules having certain biological activities that include, but are not limited to, inhibiting cell proliferation, modulating protein kinase activity and modulating polymerase activity. Molecules of the invention can modulate casein kinase (CK) activity and/or poly(ADP-ribose)polymerase (PARP) activity. The invention also relates in part to methods for using such molecules.

  本发明部分涉及具有某些生物活性的分子，包括但不限于抑制细胞增殖、调节蛋白激酶活性和调节聚合酶活性。本发明的分子可以调节酪氨酸激酶（CK）活性和/或聚(ADP核糖)聚合酶（PARP）活性。本发明部分还涉及使用这些分子的方法。
• Serine-threonine protein kinase and PARP modulators
  申请人：Senhwa Biosciences, Inc.

  公开号：EP2061765B1

  公开（公告）日：2014-10-22
• DEUTERATED SERINE-THREONINE PROTEIN KINASE MODULATORS
  申请人：HADDACH Mustapha

  公开号：US20120129849A1

  公开（公告）日：2012-05-24

  The present invention provides deuterated compounds having certain biological activities that include, but are not limited to, inhibiting cell proliferation, modulating protein kinase activity and modulating polymerase activity. The deuterated compounds of the invention can modulate casein kinase (CK) activity and/or poly(ADP-ribose)polymerase (PARP) activity. The invention also relates in part to methods for using such deuterated compounds as therapeutic agents.