1-butyl-7-hydroxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid | 75327-48-9

• 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: 1-butyl-7-hydroxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 1-butyl-1,4-dihydro-7-hydroxy-4-quinolone-3-carboxylic acid；1-butyl-7-hydroxy-4-oxoquinoline-3-carboxylic acid
• CAS: 75327-48-9
• 化学式: C₁₄H₁₅NO₄
• 分子量: 261.277
• InChiKey: TZUQEMMNWWBEMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  77.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-butyl-7-hydroxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 、 4-N[2(4-氯吡啶基)]-氨基苯腈 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以54%的产率得到1-butyl-7-((2-((4-cyanophenyl)amino)pyrimidin-4-yl)oxy)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Anti-HIV diarylpyrimidine–quinolone hybrids and their mode of action

  摘要：

  A molecular hybridization approach is a powerful tool in the design of new molecules with improved affinity and efficacy. In this context, a series of diarylpyrimidine-quinolone hybrids were synthesized and evaluated against both wt HIV-1 and mutant viral strains. The most active hybrid 5a displayed an EC50 value of 0.28 +/- 0.07 mu M against HIV-1 IIIB. A couple of enzyme-based assays clearly pinpoint a RT-targeted mechanism of action. Docking studies revealed that these hybrids could be well located in the NNIBP of HIV-1 RT despite the bulky and polar properties of a quinolone 3-carboxylic acid moiety in the molecules. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.03.037
• 作为产物：
  描述：

  2,4-二氟苯甲酰氯 在 potassium carbonate 、 三乙胺 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 10.5h， 生成 1-butyl-7-hydroxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Anti-HIV diarylpyrimidine–quinolone hybrids and their mode of action

  摘要：

  A molecular hybridization approach is a powerful tool in the design of new molecules with improved affinity and efficacy. In this context, a series of diarylpyrimidine-quinolone hybrids were synthesized and evaluated against both wt HIV-1 and mutant viral strains. The most active hybrid 5a displayed an EC50 value of 0.28 +/- 0.07 mu M against HIV-1 IIIB. A couple of enzyme-based assays clearly pinpoint a RT-targeted mechanism of action. Docking studies revealed that these hybrids could be well located in the NNIBP of HIV-1 RT despite the bulky and polar properties of a quinolone 3-carboxylic acid moiety in the molecules. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.03.037

文献信息

• Quinolonecarboxylic acid derivatives and pharmaceutical preparations
  申请人：Schering, Aktiengesellschaft

  公开号：US04289777A1

  公开（公告）日：1981-09-15

  Quinolonecarboxylic acid derivatives of the formula ##STR1## wherein the grouping ##STR2## is independently in the 6-, 7- or 8-position of each of the quinolone residues; m and n independently are each 1-4; R.sub.1 is hydrogen or alkyl of 1-6 carbon atoms; R.sub.2 is hyrogen, alkanoyl of 1-8 carbon atoms or benzoyl; and X is hydrogen, alkyl of 1-6 carbon atoms or the cation of a base which produces a physiologically acceptable salt with the quinolonecarboxylic acid, have valuable pharmacological properties.

  喹诺酸衍生物的化学式为##STR1##，其中，##STR2##在每个喹诺酮残基的6、7或8位独立存在；m和n独立地为1-4；R.sub.1为氢或1-6个碳原子的烷基；R.sub.2为氢、1-8个碳原子的脂肪酰基或苯甲酰基；X为氢、1-6个碳原子的烷基或产生与喹诺酸物理上可接受的盐的碱的阳离子。该化合物具有重要的药理学性质。
• US4289777A
  申请人：——

  公开号：US4289777A

  公开（公告）日：1981-09-15
• Anti-HIV diarylpyrimidine–quinolone hybrids and their mode of action
  作者：Tian-Qi Mao、Qiu-Qin He、Zheng-Yong Wan、Wen-Xue Chen、Fen-Er Chen、Gang-Feng Tang、Erik De Clercq、Dirk Daelemans、Christophe Pannecouque

  DOI：10.1016/j.bmc.2015.03.037

  日期：2015.7

  A molecular hybridization approach is a powerful tool in the design of new molecules with improved affinity and efficacy. In this context, a series of diarylpyrimidine-quinolone hybrids were synthesized and evaluated against both wt HIV-1 and mutant viral strains. The most active hybrid 5a displayed an EC50 value of 0.28 +/- 0.07 mu M against HIV-1 IIIB. A couple of enzyme-based assays clearly pinpoint a RT-targeted mechanism of action. Docking studies revealed that these hybrids could be well located in the NNIBP of HIV-1 RT despite the bulky and polar properties of a quinolone 3-carboxylic acid moiety in the molecules. (C) 2015 Elsevier Ltd. All rights reserved.