2-(3-甲氧基-苯基)-8-甲基-喹啉 | 107027-53-2

• 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
• 中文名称: 2-(3-甲氧基-苯基)-8-甲基-喹啉
• 英文名称: 2-(3-Methoxy-phenyl)-8-methyl-quinoline
• 英文别名: 2-(3-Methoxyphenyl)-8-methylquinoline
• CAS: 107027-53-2
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: MXBQFQXECOQLIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-甲氧基-苯基)-8-甲基-喹啉 在 chromium(VI) oxide 、 硫酸 作用下， 以 水 为溶剂， 生成 2-(3-甲氧基-苯基)-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
• 作为产物：
  描述：

  3-甲氧基苯乙酮 在 氢氧化钾 、 铜 作用下， 以 乙醇 为溶剂， 生成 2-(3-甲氧基-苯基)-8-甲基-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

• Understanding the Visible-Light-Initiated Manganese-Catalyzed Synthesis of Quinolines and Naphthyridines under Ambient and Aerobic Conditions
  作者：Kamaless Patra、Arindom Bhattacherya、Chenfei Li、Jitendra K. Bera、Han Sen Soo

  DOI：10.1021/acscatal.2c05086

  日期：2022.12.16

  scope of >30 examples under modest reaction conditions. A variety of 2-aminobenzyl alcohols containing electron-donating and electron-deficient groups and (2-aminopyridin-3-yl)methanol are converted to the corresponding quinolines and naphthyridines using ambient air as an oxidant in the presence of KOH. We synthesized a wide range of derivatives, including some of the bioactive antimalarial drug chloroquine

  多环芳烃N-杂环是天然产物和活性药物成分中一些最常见的结构单元。已经做出重大努力来开发催化方案，包括那些在高温下使用无受体脱氢策略的方案，以生产多环芳烃N-杂环，如喹啉和萘啶。然而，由可见光驱动的光引发催化提供了一种更温和且通常更具选择性的方案作为热反应的替代方案。在这里，我们展示了使用光催化剂 [Mn(L 1 H)(CO) 3 Br] (L 1 ) 从邻氨基苄醇和酮催化合成喹啉和萘啶H = 7-hydroxy-2-methyl-1,8-naphthyridine- N -oxide)，在 1,8-naphthyridine- N上带有一个酚单元-氧化物支架，在环境和有氧条件下，可见光照明。我们描述了在适度反应条件下超过 30 个示例的广泛的、官能团耐受的底物范围。在 KOH 存在的情况下，使用环境空气作为氧化剂，将各种含有供电子和缺电子基团的 2-氨基苯甲醇和 (2-氨基吡啶-3-基)