2-吡啶-3-基-喹啉-8-羧酸 | 107027-64-5

• 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
• 中文名称: 2-吡啶-3-基-喹啉-8-羧酸
• 英文名称: 2-Pyridin-3-yl-quinoline-8-carboxylic acid
• 英文别名: 2-Pyridin-3-ylquinoline-8-carboxylic acid
• CAS: 107027-64-5
• 化学式: C₁₅H₁₀N₂O₂
• 分子量: 250.257
• InChiKey: SJQYLTWGQVEXSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-二甲基乙二胺 、 2-吡啶-3-基-喹啉-8-羧酸 在 盐酸 、 N,N'-羰基二咪唑 作用下， 生成 2-Pyridin-3-yl-quinoline-8-carboxylic acid (2-dimethylamino-ethyl)-amide; hydrochloride
  参考文献：
  名称：

  Potential antitumor agents. 57. 2-Phenylquinoline-8-carboxamides as minimal DNA-intercalating antitumor agents with in vivo solid tumor activity

  摘要：

  A series of phenyl-substituted derivatives of the "minimal" DNA-intercalating agent N-[2-(dimethylamino)-ethyl]-2-phenylquinoline-8-carboxamide (1) have been synthesized and evaluated for in vivo antitumor activity, in a continuing search for active compounds of this class with the lowest possible DNA association constants. Substitution on the 2'-position of the phenyl ring gave compounds of lower DNA binding ability that did not intercalate DNA, indicating that it is necessary for the phenyl ring to be essentially coplanar with the quinoline for intercalative binding. An extensive series of 4'-substituted derivatives was evaluated, but there was no overall relationship between biological activity and substituent lipophilic or electronic properties. However, several compounds showed good solid tumor activity, with the 4'-aza derivative 18 being clearly superior to the parent compound, effecting about 50% cures in both leukemia and solid tumor models.

  DOI：

  10.1021/jm00122a018
• 作为产物：
  描述：

  7-甲基靛红 在 chromium(VI) oxide 、 氢氧化钾 、 硫酸 、 铜 作用下， 以 乙醇 、 水 为溶剂， 生成 2-吡啶-3-基-喹啉-8-羧酸
  参考文献：
  名称：

  Potential antitumor agents. 57. 2-Phenylquinoline-8-carboxamides as minimal DNA-intercalating antitumor agents with in vivo solid tumor activity

  摘要：

  A series of phenyl-substituted derivatives of the "minimal" DNA-intercalating agent N-[2-(dimethylamino)-ethyl]-2-phenylquinoline-8-carboxamide (1) have been synthesized and evaluated for in vivo antitumor activity, in a continuing search for active compounds of this class with the lowest possible DNA association constants. Substitution on the 2'-position of the phenyl ring gave compounds of lower DNA binding ability that did not intercalate DNA, indicating that it is necessary for the phenyl ring to be essentially coplanar with the quinoline for intercalative binding. An extensive series of 4'-substituted derivatives was evaluated, but there was no overall relationship between biological activity and substituent lipophilic or electronic properties. However, several compounds showed good solid tumor activity, with the 4'-aza derivative 18 being clearly superior to the parent compound, effecting about 50% cures in both leukemia and solid tumor models.

  DOI：

  10.1021/jm00122a018

文献信息

• [EN] TRICYCLIC ANTIBIOTICS<br/>[FR] ANTIBIOTIQUES TRICYCLIQUES
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2009128019A1

  公开（公告）日：2009-10-22

  The invention relates to antibacterial compounds of formula (I) wherein U represents CH or N; W represents CH or N; R1 represents alkoxy, halogen or CN; ring A represents a pyrrolidin-l,3-diyl-, a piperidin-l,3-diyl or a morpholin-2,4-diyl group and B represents CH2; or ring A is selected from the groups drawn below:formula (II) wherein R2 represents H, F or hydroxymethyl, and B is absent; G represents a group selected from the group consisting of -CH=CH-E,formula (III) and formula (IV) wherein Y1, Y2, Y3 and Z independently represent CH or N; Q represents O or S; and E represents phenyl which is mono- or di-substituted wherein the substituents are each independently halogen; and to pharmaceutically acceptable salts of such compounds.

  该发明涉及具有以下结构的抗菌化合物（I）：其中U代表CH或N；W代表CH或N；R1代表烷氧基、卤素或CN；环A代表吡咯烷-1,3-二基、哌啶-1,3-二基或吗啉-2,4-二基，B代表CH2；或者环A从下面的结构中选择：式（II）其中R2代表H、F或羟甲基，B不存在；G代表从-CH=CH-E、式（III）和式（IV）中选择的一种基团，其中Y1、Y2、Y3和Z独立地代表CH或N；Q代表O或S；E代表苯基，其是单取代或双取代的，取代基各自独立地为卤素；以及这些化合物的药用可接受盐。
• QUINOLINES AND RELATED ANALOGS AS SIRTUIN MODULATORS
  申请人：GlaxoSmithKline LLC

  公开号：EP2273992B1

  公开（公告）日：2016-05-25
• QUENOLINES AND RELATED ANALOGS AS SIRTUIN MODULATORS
  申请人：Sirtris Pharmaceuticals, Inc.

  公开号：EP2273992A1

  公开（公告）日：2011-01-19
• TRICYCLIC ANTIBIOTICS
  申请人：Actelion Pharmaceuticals Ltd.

  公开号：EP2276766A1

  公开（公告）日：2011-01-26
• [EN] QUENOLINES AND RELATED ANALOGS AS SIRTUIN MODULATORS<br/>[FR] QUINOLÉINES ET ANALOGUES APPARENTÉS EN TANT QUE MODULATEURS DE SIRTUINE
  申请人：SIRTRIS PHARMACEUTICALS INC

  公开号：WO2009134973A1

  公开（公告）日：2009-11-05

  Provided herein are novel sirtuin-modulating compounds and methods of use thereof. The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. Also provided are compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.