2-羟基喹啉-6-甲醛 | 90800-31-0

• 物质功能分类: 医药中间体 - 杂环化合物 - 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-羟基喹啉-6-甲醛
• 中文别名: 2-羟基-6-喹啉甲醛
• 英文名称: 2(1H)-quinolinone-6-carboxaldehyde
• 英文别名: 6-formylquinolin-2(1H)-one；2-oxo-1,2-dihydroquinoline-6-carbaldehyde；2-oxo-1,2-dihydro-6-quinolinecarbaldehyde；2-Hydroxyquinoline-6-carbaldehyde；2-oxo-1H-quinoline-6-carbaldehyde
• CAS: 90800-31-0
• 化学式: C₁₀H₇NO₂
• 分子量: 173.171
• InChiKey: AAPOPNBYYIWIAX-UHFFFAOYSA-N

物化性质

• 熔点：
  284-285.5℃

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  2-氯喹啉-6-甲醛	2-chloroquinoline-6-carbaldehyde	791626-59-0	C10H6ClNO	191.617
  2-氯-6-甲基喹啉	2-chloro-6-methylquinoline	4295-11-8	C10H8ClN	177.633

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  6-(羟甲基)-1H-喹啉-2-酮	6-(hydroxymethyl)quinolin-2(1H)-one	103702-27-8	C10H9NO2	175.187
  ——	6-Bromomethyl-1H-quinolin-2-one	103702-29-0	C10H8BrNO	238.084

反应信息

• 作为反应物：
  描述：

  2-羟基喹啉-6-甲醛 以 甲醇 为溶剂， 以54%的产率得到6-(羟甲基)-1H-喹啉-2-酮
  参考文献：
  名称：

  Studies on 2(1H)-quinolinone derivatives as gastric antiulcer active agents. 2-(4-Chlorobenzoylamino)-3-(2(1H)-quinolinon-4-yl)propionic acid and related compounds.

  摘要：

  合成了一系列N-酰基氨基酸类似物的2 (1H)-喹啉酮，并测试了它们对醋酸诱导的大鼠胃溃疡的抗溃疡活性。这些化合物是通过酰化2 (1H)-喹啉酮的氨基酸衍生物合成的，这些衍生物是通过ω-溴烷基2 (1H)-喹啉酮和乙酰胺基丙二酸酯在乙醇钠存在下反应，然后与稀盐酸水解得到的。其中，2-(4-氯苯甲酰氨基)-3-[2 (1H)-喹啉酮-4-基]丙酸(VIIIf)显示出最强的活性。讨论了结构活性关系。

  DOI：

  10.1248/cpb.33.3775
• 作为产物：
  描述：

  2-氯-6-甲基喹啉 在 乙酰胺 、 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 对甲苯磺酸 、 过氧化苯甲酰 作用下， 以 苯 为溶剂， 反应 10.0h， 生成 2-羟基喹啉-6-甲醛
  参考文献：
  名称：

  Identification and Specificity Studies of Small-Molecule Ligands for SH3 Protein Domains

  摘要：

  The Src Homology 3 (SH3) domains are small protein-protein interaction domains that bind proline-rich sequences and mediate a wide range of cell-signaling and other important biological processes. Since deregulated signaling pathways form the basis of many human diseases, the SH3 domains have been attractive targets for novel therapeutics. High-affinity ligands for SH3 domains have been designed; however, these have all been peptide-based and no examples of entirely nonpeptide SH3 ligands have previously been reported. Using the mouse Tec Kinase SH3 domain as a model system for structure-based ligand design, we have identified several simple heterocyclic compounds that selectively bind to the Tec SH3 domain. Using a combination of nuclear magnetic resonance chemical shift perturbation, structure-activity relationships, and site-directed mutagenesis, the binding of these compounds at the proline-rich peptide-binding site has been characterized. The most potent of these, 2-aminoquinoline, bound with K-d = 125 muM and was able to compete for binding with a proline-rich peptide. Synthesis of 6-substitued-2-aminoquinolines resulted in ligands with up to 6-fold improved affinity over 2-aminoquinoline and enhanced specificity for the Tec SH3 domain. Therefore, 2-aminoquinolines may potentially be useful for the development of high affinity small molecule ligands for SH3 domains.

  DOI：

  10.1021/jm049533z

文献信息

• ANTI-HIV COMPOUNDS
  申请人：Prosetta Antiviral, Inc.

  公开号：US20160168100A1

  公开（公告）日：2016-06-16

  This invention provides, among other things, tetrahydroisoquinolines useful for treating viral infections, pharmaceutical formulations containing such compounds, as well as methods of inhibiting the replication of a virus, such as HIV, or treating a disease, such as AIDS.

  这项发明提供了用于治疗病毒感染的四氢异喹啉等化合物，含有这类化合物的药物配方，以及抑制病毒（如HIV）复制或治疗疾病（如艾滋病）的方法。
• [EN] NEW BICYCLIC DERIVATIVES HAVING BETA2 ADRENERGIC AGONIST AND M3 MUSCARINIC ANTAGONIST ACTIVITIES<br/>[FR] NOUVEAUX DÉRIVÉS BICYCLIQUES PRÉSENTANT UNE ACTIVITÉ AGONISTE DU RÉCEPTEUR BÊTA-2 ADRÉNERGIQUE ET UNE ACTIVITÉ ANTAGONISTE DU RÉCEPTEUR MUSCARINIQUE M3
  申请人：ALMIRALL SA

  公开号：WO2016046390A1

  公开（公告）日：2016-03-31

  The present invention relates to novel compounds having β2 adrenergic agonist and M3 muscarinic antagonist dual activity, to pharmaceutical compositions containing them, to the process for their preparation and to their use in respiratory therapies.

  本发明涉及具有β2肾上腺素受体激动剂和M3肌样受体拮抗剂双重活性的新化合物，包含它们的药物组合物，它们的制备过程以及它们在呼吸疗法中的应用。
• Bicyclic derivatives having β2 adrenergic agonist and M3 muscarinic antagonist activities
  申请人：Almirall, S.A.

  公开号：US10005771B2

  公开（公告）日：2018-06-26

  The present invention relates to novel compounds having β2 adrenergic agonist and M3 muscarinic antagonist dual activity, to pharmaceutical compositions containing them, to the process for their preparation and to their use in respiratory therapies.

  本发明涉及具有β2肾上腺素能激动剂和M3毒蕈碱拮抗剂双重活性的新型化合物、含有这些化合物的药物组合物、其制备过程以及在呼吸治疗中的应用。
• 2-phenethenyltetrahydro isoquinolines useful as anti-HIV compounds
  申请人：Prosetta Antiviral, Inc.

  公开号：US10195189B2

  公开（公告）日：2019-02-05

  This invention provides, among other things, tetrahydroisoquinolines useful for treating viral infections, pharmaceutical formulations containing such compounds, as well as methods of inhibiting the replication of a virus, such as HIV, or treating a disease, such as AIDS.

  除其他外，本发明还提供了用于治疗病毒感染的四氢异喹啉类化合物、含有此类化合物的药物制剂，以及抑制艾滋病毒等病毒复制或治疗艾滋病等疾病的方法。
• Carbostyril derivatives
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0382185B1

  公开（公告）日：1994-06-15