2-(2-呋喃基)-4-喹啉羧酸 | 20146-25-2

• 物质功能分类: 医药中间体 - 喹啉类化合物
• 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-(2-呋喃基)-4-喹啉羧酸
• 英文名称: 2-(furan-2-yl)quinoline-4-carboxylic acid
• 英文别名: 2--cinchoninsaeure
• CAS: 20146-25-2
• 化学式: C₁₄H₉NO₃
• mdl: MFCD00092384
• 分子量: 239.23
• InChiKey: WWEKTFINADFAEC-UHFFFAOYSA-N

物化性质

• 熔点：
  227 °C
• 沸点：
  433.7±40.0 °C(Predicted)
• 密度：
  1.348±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 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：
  63.3
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-(2-呋喃基)-4-喹啉羧酸 在 air 作用下， 以 二甲基亚砜 为溶剂， 反应 912.0h， 生成 2-羟基喹啉-4-羧酸
  参考文献：
  名称：

  Oxidative Reactivities of 2-Furylquinolines: Ubiquitous Scaffolds in Common High-Throughput Screening Libraries

  摘要：

  High-throughput screening (HTS) was employed to discover APOBEC3G inhibitors, and multiple 2-furylquinolines (e.g., 1) were found. Dose response assays with 1 from the HTS sample, as well as commercial material, yielded similar confirmatory results. Interestingly, freshly synthesized and DMSO-solubilized 1 was inactive. Repeated screening of the DMSO aliquot of synthesized 1 revealed increasing APOBEC3G inhibitory activity with age, suggesting that 1 decomposes into an active inhibitor. Laboratory aging of 1 followed by analysis revealed that 1 undergoes oxidative decomposition in air, resulting from a [4 + 2] cycloaddition between the furan of 1 and O-1(2). The resulting endoperoxide then undergoes additional transformations, highlighted by Baeyer-Villager rearrangements, to deliver lactam, carboxylic acid, and aldehyde products. The endoperoxide also undergoes hydrolytic opening followed by further transformations to a bis-enone. Eight structurally related analogues from HTS libraries were similarly reactive. This study constitutes a cautionary tale to validate 2-furylquinolines for structure and stability prior to chemical optimization campaigns.

  DOI：

  10.1021/acs.jmedchem.5b00930
• 作为产物：
  描述：

  3-(2-(furan-2-yl)-2-oxoethyl)-3-hydroxyindolin-2-one 在 氢氧化钾 作用下， 生成 2-(2-呋喃基)-4-喹啉羧酸
  参考文献：
  名称：

  Maxim; Popescu, 1942, vol. 6, p. 140,145

  摘要：

  DOI：

文献信息

• Development of broad-spectrum enterovirus antivirals based on quinoline scaffold
  作者：Rami Musharrafieh、Naoya Kitamura、Yanmei Hu、Jun Wang

  DOI：10.1016/j.bioorg.2020.103981

  日期：2020.8

  developing potent and broad-spectrum antivirals against these non-polio enteroviruses. Starting from our previously developed lead compounds that had potent antiviral activity against EV-D68, we synthesized 43 analogs and profiled their broad-spectrum antiviral activity against additional EV-D68, EV-A71, and CVB3 viruses. Promising candidates were also selected for mouse microsomal stability test to prioritize

  非脊髓灰质炎肠道病毒，如肠道病毒 A71 (EV-A71)、EV-D68 和柯萨奇病毒 B3 (CVB3) 是重要的人类病原体，其疾病表现范围从轻微的流感样症状到更严重的脑炎、心肌炎、急性弛缓性麻痹/脊髓炎，甚至死亡。目前没有有效的抗病毒药物来预防或治疗非脊髓灰质炎肠道病毒感染。在这项研究中，我们报告了我们在开发针对这些非脊髓灰质炎肠道病毒的强效广谱抗病毒药物方面的进展。从我们之前开发的对 EV-D68 具有强效抗病毒活性的先导化合物开始，我们合成了 43 种类似物，并分析了它们对其他 EV-D68、EV-A71 和 CVB3 病毒的广谱抗病毒活性。还选择了有希望的候选者进行小鼠微粒体稳定性测试，以便为未来的体内小鼠模型研究优先考虑先导化合物。总的来说，这种多参数优化过程揭示了一种有前途的先导化合物6aw对两种 EV-D68 菌株（US/KY 和 US/MO）、两种 EV-A71 菌株（台南和美国/AK）和一种
• [EN] CHROMOBOX PROTEIN INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE PROTÉINE CHROMOBOX ET LEURS UTILISATIONS
  申请人：DANA FARBER CANCER INST INC

  公开号：WO2018058029A1

  公开（公告）日：2018-03-29

  Provided herein are compounds useful as inhibitors of CBX. Also described are pharmaceutical compositions and medical uses of these compounds.

  本文提供了作为CBX抑制剂有用的化合物。同时描述了这些化合物的药物组成和医药用途。
• Novel Fluorene Derivatives, Composition Containing Said Derivatives and the Use Thereof
  申请人：MAILLIET Patrick

  公开号：US20080153837A1

  公开（公告）日：2008-06-26

  This invention relates to derivatives of 4-(benzimidazol-2-yl)fluorene and 4-(azabenzimidazol-2-yl)fluorene, to pharmaceutical compositions comprising such derivatives, and to methods of treatment of disorders related to Hsp90 protein activity, comprising administering such derivatives.

  这项发明涉及4-(苯并咪唑-2-基)芴和4-(氮杂苯并咪唑-2-基)芴的衍生物，涉及包含这些衍生物的药物组合物，以及涉及治疗与Hsp90蛋白活性相关的疾病的方法，包括给予这些衍生物。
• Synthesis and structure–activity relationship of disubstituted benzamides as a novel class of antimalarial agents
  作者：Katsuhiko Mitachi、Yandira G. Salinas、Michele Connelly、Nicholas Jensen、Taotao Ling、Fatima Rivas

  DOI：10.1016/j.bmcl.2012.05.124

  日期：2012.7

  identified a novel series of disubstituted benzamide compounds with significant activity against malaria strains 3D7 and K1. These compounds represent a new antimalarial molecular scaffold exemplified by compound 1, which demonstrated EC50 values of 60 and 430 nM against strains 3D7 and K1, respectively. Herein we report our findings on the efficient synthesis, structure–activity relationships, and biological

  疟疾是一个毁灭性的世界卫生问题。使用化合物库筛选方法，我们确定了一系列对疟疾菌株3D7和K1具有显着活性的新型双取代苯甲酰胺化合物。这些化合物代表了一种新的抗疟疾分子支架，以化合物1为例，其针对菌株3D7和K1的EC 50值分别为60和430 nM。本文中，我们报告了有关这一新型抗疟疾药物的有效合成，构效关系和生物学活性的发现。
• Discovery of a Novel Class of Selective Non-Peptide Antagonists for the Human Neurokinin-3 Receptor. 1. Identification of the 4-Quinolinecarboxamide Framework
  作者：Giuseppe A. M. Giardina、Henry M. Sarau、Carlo Farina、Andrew D. Medhurst、Mario Grugni、Luca F. Raveglia、Dulcie B. Schmidt、Roberto Rigolio、Mark Luttmann、Vittorio Vecchietti、Douglas W. P. Hay

  DOI：10.1021/jm960818o

  日期：1997.6.1

  A novel class of potent and selective non-peptide neurokinin-3 (NK-3) receptor antagonists, featuring the 4-quinolinecarboxamide framework, has been designed based upon chemically diverse NK-1 receptor antagonists. The novel compounds 33-76, prompted by chemical modifications of the prototype 4, have been characterized by binding analysis using a membrane preparation of chinese hamster ovary (CHO)

  基于化学上不同的NK-1受体拮抗剂，设计了一种新型的有效且选择性的非肽神经激肽3（NK-3）受体拮抗剂，其特征在于4-喹啉羧酰胺骨架。通过原型4的化学修饰促进了新型化合物33-76的表达，其特征在于使用表达人神经激肽3受体（hNK-3-CHO）的中国仓鼠卵巢（CHO）细胞膜制剂进行结合分析，并建立了明确的结构-活性关系（SAR）。从SARs（R）-N- [α-（甲氧基羰基）苄基] -2-苯基喹啉-4-羧酰胺（65，SB 218795，hNK-3-CHO结合Ki = 13 nM）出现，是最有效的化合物之一这个新颖的班级。对其他神经激肽受体（hNK-2-CHO和hNK-1-CHO）的选择性研究表明，对hNK-3的选择性是对hNK-2受体的65倍（hNK-2-CHO结合Ki = 1221 nM）。相对于hNK-1受体具有超过7000倍的选择性（hNK-1-CHO结合Ki => 100 micro