methyl 3-(methylthio)-5-phenylpyrimido[4,5-c]quinoline-8-carboxylate | 1140903-64-5

• 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 3-(methylthio)-5-phenylpyrimido[4,5-c]quinoline-8-carboxylate
• 英文别名: methyl 3-methylsulfanyl-5-phenylpyrimido[4,5-c]quinoline-8-carboxylate
• CAS: 1140903-64-5
• 化学式: C₂₀H₁₅N₃O₂S
• 分子量: 361.424
• InChiKey: YPDRWIVEUCVXRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  90.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-(methylthio)-5-phenylpyrimido[4,5-c]quinoline-8-carboxylate 在 间氯过氧苯甲酸 、 sodium hydroxide 作用下， 以 N-甲基吡咯烷酮 、 乙醇 、 二氯甲烷 为溶剂， 生成 3-(cyclopropylamino)-5-phenylpyrimido[4,5-c]quinoline-8-carboxylic acid
  参考文献：
  名称：

  Synthesis and SAR of inhibitors of protein kinase CK2: Novel tricyclic quinoline analogs

  摘要：

  Protein kinase CK2 is a potential drug target for many diseases including cancer and inflammation disorders. The crystal structure of clinical candidate CX-4945 1 with CK2 revealed an indirect interaction with the protein through hydrogen bonding between the NH of the 3-chlorophenyl amine and a water molecule. Herein, we investigate the relevance of this hydrogen bond by preparing several novel tricyclic derivatives lacking a NH moiety at the same position. This SAR study allowed the discovery of highly potent CK2 inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.087
• 作为产物：
  描述：

  methyl 5-chloro-3-(methylthio)pyrimido[4,5-c]quinoline-8-carboxylate 、 苯硼酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.17h， 以84%的产率得到methyl 3-(methylthio)-5-phenylpyrimido[4,5-c]quinoline-8-carboxylate
  参考文献：
  名称：

  THERAPEUTIC KINASE MODULATORS

  摘要：

  该发明涉及部分具有特定生物活性的分子，包括但不限于抑制细胞增殖和调节蛋白激酶活性。该发明的分子可以调节酪蛋白激酶（CK）活性。该发明还涉及使用这些分子的方法。

  公开号：

  US20090093465A1

文献信息

• Therapeutic kinase modulators
  申请人：Cylene Pharmaceuticals, Inc.

  公开号：US07910600B2

  公开（公告）日：2011-03-22

  The invention relates in part to molecules having certain biological activities that include, but are not limited to, inhibiting cell proliferation, and modulating protein kinase activity. Molecules of the invention can modulate casein kinase (CK) 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和调节蛋白激酶活性。本发明的分子可以调节酪蛋白激酶（CK）活性。本发明还涉及使用这些分子的方法。
• US7910600B2
  申请人：——

  公开号：US7910600B2

  公开（公告）日：2011-03-22
• [EN] THERAPEUTIC KINASE MODULATORS<br/>[FR] MODULATEURS DE KINASE THÉRAPEUTIQUES
  申请人：CYLENE PHARMACEUTICALS INC

  公开号：WO2009097014A2

  公开（公告）日：2009-08-06

  The invention relates in part to molecules having certain biological activities that include, but are not limited to, inhibiting cell proliferation, and modulating protein kinase activity. Molecules of the invention can modulate casein kinase (CK) activity. The invention also relates in part to methods for using such molecules.
• Synthesis and SAR of inhibitors of protein kinase CK2: Novel tricyclic quinoline analogs
  作者：Mustapha Haddach、Fabrice Pierre、Collin F. Regan、Cosmin Borsan、Jerome Michaux、Eric Stefan、Pauline Kerdoncuff、Michael K. Schwaebe、Peter C. Chua、Adam Siddiqui-Jain、Diwata Macalino、Denis Drygin、Sean E. O’Brien、William G. Rice、David M. Ryckman

  DOI：10.1016/j.bmcl.2011.11.087

  日期：2012.1

  Protein kinase CK2 is a potential drug target for many diseases including cancer and inflammation disorders. The crystal structure of clinical candidate CX-4945 1 with CK2 revealed an indirect interaction with the protein through hydrogen bonding between the NH of the 3-chlorophenyl amine and a water molecule. Herein, we investigate the relevance of this hydrogen bond by preparing several novel tricyclic derivatives lacking a NH moiety at the same position. This SAR study allowed the discovery of highly potent CK2 inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.
• THERAPEUTIC KINASE MODULATORS
  申请人：PIERRE Fabrice

  公开号：US20090093465A1

  公开（公告）日：2009-04-09

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

  该发明涉及部分具有特定生物活性的分子，包括但不限于抑制细胞增殖和调节蛋白激酶活性。该发明的分子可以调节酪蛋白激酶（CK）活性。该发明还涉及使用这些分子的方法。