2-(2'-pyridyl)quinoline-5,8-quinone | 73688-79-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(2'-pyridyl)quinoline-5,8-quinone
• 英文别名: 2-Pyridin-2-ylquinoline-5,8-dione
• CAS: 73688-79-6
• 化学式: C₁₄H₈N₂O₂
• 分子量: 236.23
• InChiKey: IMKICXUWHQYHMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙烯亚胺 、 2-(2'-pyridyl)quinoline-5,8-quinone 以 甲醇 为溶剂， 反应 2.0h， 以38%的产率得到6-(Aziridin-1-yl)-2-pyridin-2-ylquinoline-5,8-dione
  参考文献：
  名称：

  Design of quinolinedione-Based geldanamycin analogues

  摘要：

  Quinoline-5,8-dione-based compounds were designed from the structure of the geldanamycin-bound Hsp-90 active site. The active site model predicted that aromatic substituents should be present at the 2-position, to take advantage of a hydrophobic pocket, and amino substituents should be present at the 6- or 7-position. COMPARE analysis revealed that the LC50 profile of 2-phenyl-6-(2-chloroethylamino)quinoline-5,8-dione has the highest geldanamycin-like activity (0.74 correlation coefficient). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00650-4
• 作为产物：
  描述：

  2-(2'-pyridyl)-5,8-dimethoxyquinoline 在 ammonium cerium(IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 0.75h， 生成 2-(2'-pyridyl)quinoline-5,8-quinone
  参考文献：
  名称：

  Design of quinolinedione-Based geldanamycin analogues

  摘要：

  Quinoline-5,8-dione-based compounds were designed from the structure of the geldanamycin-bound Hsp-90 active site. The active site model predicted that aromatic substituents should be present at the 2-position, to take advantage of a hydrophobic pocket, and amino substituents should be present at the 6- or 7-position. COMPARE analysis revealed that the LC50 profile of 2-phenyl-6-(2-chloroethylamino)quinoline-5,8-dione has the highest geldanamycin-like activity (0.74 correlation coefficient). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00650-4

文献信息

• LAVENDAMYCIN ANALOGS, QUINOLINE-5,8-DIONES AND METHODS OF USING THEM
  申请人：Ball State University

  公开号：US20040248922A1

  公开（公告）日：2004-12-09

  The invention provides novel lavendamycin analogs having the following general formula: 1 and quinoline-5,8-diones having the following formula: 2 Methods of making and using and compositions containing these compounds are also disclosed.

  本发明提供了具有以下一般式的新型薰衣草霉素类似物：1，以及具有以下式子的喹啉-5,8-二酮：2。还公开了制备和使用这些化合物以及含有这些化合物的组合物的方法。
• Incorporation of the quinoline-5,8-quinone moiety into polyaza cavities
  作者：Randolph P. Thummel、Sara Chirayil、Christophe Hery、Jean Luc Lim、Tie Lin Wang

  DOI：10.1021/jo00059a012

  日期：1993.3

  Silica gel supported nitric acid treatment of 2,5-dimethoxybenzaldehyde followed by reduction with iron powder provides 3,6-dimethoxy-2-aminobenzaldehyde. Friedlander condensation of this species with a variety of ketones and diketones leads to 5,8-dimethoxyquinoline derivatives which may be oxidized by ceric ammonium nitrate (CAN) and pyridine-2,6-dicarboxylic acid N-oxide (PDANO) to the corresponding quinones. The quinone functionality can be incorporated into larger cavities by a selective stepwise Friedlander approach and the CAN/PDANO oxidation appears to work preferentially for 5,8-dimethoxyquinoline.
• LAVENDAMYCIN ANALOGS, THEIR USE AND PREPARATION
  申请人：BEHFOROUZ, Mohammad

  公开号：EP0701557A1

  公开（公告）日：1996-03-20
• EP0701557A4
  申请人：——

  公开号：EP0701557A4

  公开（公告）日：1997-07-09
• US5525611A
  申请人：——

  公开号：US5525611A

  公开（公告）日：1996-06-11