8-甲基-2-吡啶-4-基-喹啉 | 107027-54-3

• 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
• 中文名称: 8-甲基-2-吡啶-4-基-喹啉
• 英文名称: 8-methyl-2-(pyridin-4-yl)quinoline
• 英文别名: 8-Methyl-2-pyridin-4-ylquinoline
• CAS: 107027-54-3
• 化学式: C₁₅H₁₂N₂
• 分子量: 220.274
• InChiKey: CNZJITWDUOYAMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-甲基-2-吡啶-4-基-喹啉 在 chromium(VI) oxide 、 硫酸 作用下， 以 水 为溶剂， 生成 2-(4-pyridyl)-8-quinolinecarboxylic acid
  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 氢氧化钾 、 铜 作用下， 以 乙醇 为溶剂， 生成 8-甲基-2-吡啶-4-基-喹啉
  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

• Dna-targeted benzotriazine 1,4-dioxides and their use in cancer therapy
  申请人：Brown Martin J.

  公开号：US20070191372A1

  公开（公告）日：2007-08-16

  The present invention relates to DNA-targeted 1,2,4-benzotriazine-1,4-dioxides and related analogues, to their preparation, and to their use as hypoxia-selective drugs and radiosensitizers for cancer therapy, both alone or in combination with radiation and/or other anticancer drugs.

  本发明涉及以DNA为靶点的1,2,4-苯并三氮唑-1,4-二氧化物及其相关类似物，其制备方法以及它们作为低氧选择性药物和放射增敏剂在癌症治疗中的使用，可以单独使用或与放射线和/或其他抗癌药物结合使用。
• Cathodically Coupled Electrolysis to Access Biheteroaryls
  作者：Tianyu He、Chaoqiang Liang、Haoyuan Cheng、Shuai Shi、Shenlin Huang

  DOI：10.1021/acs.orglett.3c03859

  日期：2024.1.26

  An electrochemical approach to biheteroaryls through the coupling of diverse N-heteroarenes with heteroaryl phosphonium salts is reported. The reaction features pH and redox-neutral conditions and excellent regioselectivity, as well as exogenous air or moisture tolerance. Additionally, a one-pot, two-step protocol can be established to realize formal C–H/C–H coupling of heteroarenes, thereby greatly

  报道了通过多种N-杂芳烃与杂芳基鏻盐的偶联来制备联杂芳基的电化学方法。该反应具有 pH 值和氧化还原中性条件、出色的区域选择性以及外源空气或水分耐受性。此外，可以建立一锅两步方案来实现杂芳烃的正式C-H/C-H偶联，从而大大扩展底物可用性。通过后期功能化、硝基吡啶的全合成和抗真菌活性研究证明了该方法的实用性。
• Potential antitumor agents. 57. 2-Phenylquinoline-8-carboxamides as minimal DNA-intercalating antitumor agents with in vivo solid tumor activity
  作者：Graham J. Atwell、Bruce C. Baguley、William A. Denny

  DOI：10.1021/jm00122a018

  日期：1989.2

  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.