5-(3-Carbamoylphenyl)benzo[c][2,6]naphthyridine-8-carboxylic acid | 1354912-44-9

• 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: 5-(3-Carbamoylphenyl)benzo[c][2,6]naphthyridine-8-carboxylic acid
• CAS: 1354912-44-9
• 化学式: C₂₀H₁₃N₃O₃
• 分子量: 343.342
• InChiKey: DOHNTCFPJHBCEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 生成 5-(3-Carbamoylphenyl)benzo[c][2,6]naphthyridine-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

文献信息

• 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.