2-methyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid | 53977-31-4

• 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: 2-methyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
• 英文别名: 2-methyl-4-quinolone-3-carboxylic acid；2-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid；4-Hydroxy-2-methylquinoline-3-carboxylic acid；2-methyl-4-oxo-1H-quinoline-3-carboxylic acid
• CAS: 53977-31-4
• 化学式: C₁₁H₉NO₃
• 分子量: 203.197
• InChiKey: IDQGHAXJWZLPCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid 生成 4-羟基-2-甲基喹啉
  参考文献：
  名称：

  Camps, Chemische Berichte, 1901, vol. 34, p. 2709

  摘要：

  DOI：
• 作为产物：
  描述：

  乙基2-甲基-4-氧代-1H-喹啉-3-羧酸酯 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 生成 2-methyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
  参考文献：
  名称：

  Identification of 4-hydroxyquinolines inhibitors of p300/CBP histone acetyltransferases

  摘要：

  We identified a series of 4-hydroxyquinolines bearing a C1 to C15 alkyl chain at the C2 position and a carbethoxy/carboxy group at the C3 position of the quinoline nucleus (MC compounds), endowed with selective inhibitory activity against the p300/CBP HAT enzymes. Enzyme inhibition was investigated using in vitro HAT assays and by western blot analysis of cellular lysates to examine the acetylation levels of histone H3 and alpha-tubulin. When tested in U937 cells, some compounds displayed pro-apoptotic or cytodifferentiating properties. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.097

文献信息

• Novel quinolone-3-carboxylic acid derivatives as anti-HIV-1 agents: design, synthesis, and biological activities
  作者：Z. Hajimahdi、R. Zabihollahi、M. R. Aghasadeghi、S. Hosseini Ashtiani、A. Zarghi

  DOI：10.1007/s00044-016-1631-x

  日期：2016.9

  positions were synthesized and evaluated for their activity against single-cycle replicable HIV NL4-3 as inhibition rate of p24 expression in Hela cells cultures. Most of the synthesized compounds showed anti-HIV activity with no significant cytotoxicity at concentration of 100 μM. The most active compounds 4h, 4k, and 4j exhibited anti-HIV activity with an inhibition rate of 55, 71, and 84 %, respectively

  合成了一系列新的喹诺酮-3-羧酸，它们在N-1，C-2，C-7和C-8位置具有不同的疏水基团，并评估了它们对单周期可复制HIV NL4-3的抑制作用Hela细胞培养物中p 24的表达速率。大多数合成的化合物在100μM的浓度下均具有抗HIV活性，且无明显的细胞毒性。活性最高的化合物4h，4k和4j表现出抗HIV活性，抑制率分别为55％，71％和84％。使用可用于PFV整合酶的晶体学数据（包括其与Mg 2+的配合物）进行的对接研究Raltegravir和Raltegravir揭示，活性化合物可以在Raltegravir附近占据相同的空间，并与活性位点中的Mg 2 +离子相互作用。因此，合成化合物的抗HIV活性可能涉及金属螯合机制。
• Antibacterial agents
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0326891A2

  公开（公告）日：1989-08-09

  Novel naphthyridine-, and quinolinecarboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.

  介绍了作为抗菌剂的新型萘啶酸和喹啉羧酸及其制造、配制和用于治疗细菌感染的方法，包括用于制造抗菌剂的某些新型中间体。
• Overmyer, Journal of the American Chemical Society, 1926, vol. 48, p. 455
  作者：Overmyer

  DOI：——

  日期：——
• Isatoic Anhydride. IV. Reactions with Various Nucleophiles
  作者：ROGER P. STAIGER、EMERY B. MILLER

  DOI：10.1021/jo01091a013

  日期：1959.9
• Synthesis and isomeric conversions of several 2-substituted 1,4-dihydro-4-oxo-3-quinolinecarboxylic acid derivatives
  作者：L. I. Kononov、G. A. Veinberg、�. �. Liepin'sh、I. V. Dipan、N. M. Sukhova、�. Lukevits

  DOI：10.1007/bf00633172

  日期：1988.7