5-(3-Chloroanilino)benzo[c][2,6]naphthyridine-9-carboxamide | 1350624-88-2

• 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: 5-(3-Chloroanilino)benzo[c][2,6]naphthyridine-9-carboxamide
• CAS: 1350624-88-2
• 化学式: C₁₉H₁₃ClN₄O
• 分子量: 348.791
• InChiKey: CGKRFSJIEAWXSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 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：
  80.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-(3-chlorophenylamino)benzo[c][2,6]naphthyridine-9-carboxylic acid 在 氯化铵 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N-甲基吡咯烷酮 为溶剂， 生成 5-(3-Chloroanilino)benzo[c][2,6]naphthyridine-9-carboxamide
  参考文献：
  名称：

  7-(4H-1,2,4-Triazol-3-yl)benzo[c][2,6]naphthyridines: A novel class of Pim kinase inhibitors with potent cell antiproliferative activity

  摘要：

  A novel class of pan-Pim kinase inhibitors was designed by modifying the CK2 inhibitor CX-4945. Introduction of a triazole or secondary amide functionality on the C-7 position and 2'-halogenoanilines on C-5 resulted in potent inhibitors of the Pim-1 and Pim-2 isoforms, with many analogs active at single digit nanomolar concentrations. The molecules inhibited the phosphorylation at Serine 112 of the apoptosis effector BAD, and had potent antiproliferative effects on the AML cell line MV-4-11 ( IC50 < 30 nM). This work delivers an excellent lead-optimization platform for Pim targeting anticancer therapies. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.059

文献信息

• 7-(4H-1,2,4-Triazol-3-yl)benzo[c][2,6]naphthyridines: A novel class of Pim kinase inhibitors with potent cell antiproliferative activity
  作者：Fabrice Pierre、Eric Stefan、Anne-Sophie Nédellec、Marie-Claire Chevrel、Collin F. Regan、Adam Siddiqui-Jain、Diwata Macalino、Nicole Streiner、Denis Drygin、Mustapha Haddach、Sean E. O’Brien、Kenna Anderes、David M. Ryckman

  DOI：10.1016/j.bmcl.2011.09.059

  日期：2011.11

  A novel class of pan-Pim kinase inhibitors was designed by modifying the CK2 inhibitor CX-4945. Introduction of a triazole or secondary amide functionality on the C-7 position and 2'-halogenoanilines on C-5 resulted in potent inhibitors of the Pim-1 and Pim-2 isoforms, with many analogs active at single digit nanomolar concentrations. The molecules inhibited the phosphorylation at Serine 112 of the apoptosis effector BAD, and had potent antiproliferative effects on the AML cell line MV-4-11 ( IC50 < 30 nM). This work delivers an excellent lead-optimization platform for Pim targeting anticancer therapies. (C) 2011 Elsevier Ltd. All rights reserved.