7-[苯胺基(苯基)甲基]喹啉-8-醇 | 5335-95-5

• 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: 7-[苯胺基(苯基)甲基]喹啉-8-醇
• 英文名称: 8-hydroxy-7-(α-anilino-benzyl)-quinoline
• 英文别名: 7-(phenyl(phenylamino)methyl)quinolin-8-ol；7-(phenyl-phenylaminomethyl)quinolin-8-ol；NSC1008；7-(anilino-phenyl-methyl)-quinolin-8-ol；7-(α-anilino-benzyl)-quinolin-8-ol；7-(α-Anilino-benzyl)-chinolin-8-ol；7-[Phenyl(phenylamino)methyl]quinolin-8-ol；7-[anilino(phenyl)methyl]quinolin-8-ol
• CAS: 5335-95-5
• 化学式: C₂₂H₁₈N₂O
• 分子量: 326.398
• InChiKey: OTNAVATYWOEDMK-UHFFFAOYSA-N

物化性质

• 熔点：
  146-147 °C
• 沸点：
  529.9±45.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  45.2
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  7-[苯胺基(苯基)甲基]喹啉-8-醇 在 manganese salt 作用下， 以 乙醇 、 氨 、 水 为溶剂， 生成
  参考文献：
  名称：

  Chelate Compounds of 7-(α-Anilinobenzyl)-8-quinolinol

  摘要：

  DOI：

  10.1021/ja01626a018
• 作为产物：
  描述：

  8-羟基喹啉 、 N-苄叉苯胺 在 乙醇 作用下， 生成 7-[苯胺基(苯基)甲基]喹啉-8-醇
  参考文献：
  名称：

  Pirrone, Gazzetta Chimica Italiana, 1941, vol. 71, p. 320,325

  摘要：

  DOI：

文献信息

• Identification of Quinolinols as Activators of TEAD-Dependent Transcription
  作者：Ajaybabu V. Pobbati、Tom Mejuch、Sayan Chakraborty、Hacer Karatas、Sakshibeedu R. Bharath、Stéphanie M. Guéret、Pierre-Alexis Goy、Gernot Hahne、Axel Pahl、Sonja Sievers、Ernesto Guccione、Haiwei Song、Herbert Waldmann、Wanjin Hong

  DOI：10.1021/acschembio.9b00786

  日期：2019.12.20

  has been physiologically shown to bind palmitate. Herein, a TEAD-palmitate interaction screen was developed to select small molecules occupying the palmitate-binding pocket (PBP) of TEADs. We show that quinolinols were TEAD-binding compounds that augment YAP/TAZ-TEAD activity, which was verified using TEAD reporter assay, RT-qPCR, and RNA-Seq analyses. Structure-activity relationship investigations uncovered

  转录共调节因子YAP（Yes相关蛋白）和TAZ（具有PDZ结合基序的转录共激活因子）是控制各种生理和病理过程的河马信号通路的脊椎动物下游效应子。YAP和TAZ与TEAD（TEA域）家族的转录因子配对以启动转录。我们先前在TEADs中发现了一个易处理的口袋，从生理学角度来看，它可以与棕榈酸酯结合。本文中，开发了TEAD-棕榈酸酯相互作用筛选以选择占据TEAD的棕榈酸酯结合袋（PBP）的小分子。我们显示，喹啉醇是TEAD结合的化合物，可增加YAP / TAZ-TEAD活性，已通过TEAD报告基因分析，RT-qPCR和RNA-Seq分析进行了验证。结构-活性关系研究发现了TEAD激活所必需的喹啉醇取代基。我们揭示了一种新的机制，其中喹啉酚通过占据PBP来稳定YAP / TAZ蛋白水平。在小鼠伤口愈合模型中，喹啉醇提高了YAP活性，加速了体内伤口的闭合。尽管占据PBP的小分子已显示抑制YAP /
• Novel Quinoline-Hepcidine Antagonists
  申请人：Dürrenberger Franz

  公开号：US20120196853A1

  公开（公告）日：2012-08-02

  The present invention relates to novel hepcidin antagonists of the general formula (I), pharmaceutical compositions comprising them and the use thereof as medicaments, in particular for treatment of disorders in iron metabolism, such as, in particular, iron deficiency diseases and anaemias, in particular anaemias in connection with chronic inflammatory diseases (ACD: anaemia of chronic disease and AI: anaemia of inflammation).

  本发明涉及一种新型的肝铁蛋白拮抗剂，其一般式为(I)，包括它们的药物组合物以及将其用作药物的用途，特别是用于治疗铁代谢紊乱的疾病，如特别是铁缺乏病和贫血，特别是与慢性炎症性疾病相关的贫血（ACD：慢性疾病贫血和AI：炎症性贫血）。
• Synthesis and Cytoprotective Characterization of 8-Hydroxyquinoline Betti Products
  作者：Iván Kanizsai、Ramóna Madácsi、László Hackler、Márió Gyuris、Gábor J. Szebeni、Orsolya Huzián、László G. Puskás

  DOI：10.3390/molecules23081934

  日期：——

  The 8-hydroxyquinoline pharmacophore scaffold has been shown to possess a range of activities as metal chelation, enzyme inhibition, cytotoxicity, and cytoprotection. Based on our previous findings we set out to optimize the scaffold for cytoprotective activity for its potential application in central nervous system related diseases. A 48-membered Betti-library was constructed by the utilization of

  已经证明8-羟基喹啉药效团支架具有一系列活性，例如金属螯合，酶抑制，细胞毒性和细胞保护。基于我们以前的发现，我们着手优化支架的细胞保护活性，以使其潜在地应用于中枢神经系统相关疾病。通过利用甲酸介导的工业相容性偶联物，与苯胺，恶唑，吡啶和嘧啶等芳香族伯胺，以及（杂）芳族醛和8-氢氧喹啉衍生物，构建48位成员的Betti库。经柱层析和重结晶后，得到相应的类似物，产率为13-90％。通过利用化学诱导的氧化应激的细胞保护测定法对合成的类似物进行了优化，并在正交测定，实时细胞生存力方法，基于荧光激活细胞分选（FACS）的测定线粒体膜电位变化的测定以及基因表达分析中进一步测试了活性最高的化合物。最好的候选者在所有测试系统中均显示出强大的纳摩尔活性，并支持将来需要对中枢神经系统（CNS）疾病的动物模型进行研究。
• 8-Hydroxyquinoline-based inhibitors of the Rce1 protease disrupt Ras membrane localization in human cells
  作者：Idrees Mohammed、Shahienaz E. Hampton、Louise Ashall、Emily R. Hildebrandt、Robert A. Kutlik、Surya P. Manandhar、Brandon J. Floyd、Haley E. Smith、Jonathan K. Dozier、Mark D. Distefano、Walter K. Schmidt、Timothy M. Dore

  DOI：10.1016/j.bmc.2015.11.043

  日期：2016.1

  Ras converting enzyme 1 (Rce1) is an endoprotease that catalyzes processing of the C-terminus of Ras protein by removing -aaX from the CaaX motif. The activity of Rce1 is crucial for proper localization of Ras to the plasma membrane where it functions. Ras is responsible for transmitting signals related to cell proliferation, cell cycle progression, and apoptosis. The disregulation of these pathways due to constitutively active oncogenic Ras can ultimately lead to cancer. Ras, its effectors and regulators, and the enzymes that are involved in its maturation process are all targets for anti-cancer therapeutics. Key enzymes required for Ras maturation and localization are the farnesyltransferase (FTase), Rce1, and isoprenylcysteine carboxyl methyltransferase (ICMT). Among these proteins, the physiological role of Rce1 in regulating Ras and other CaaX proteins has not been fully explored. Small-molecule inhibitors of Rce1 could be useful as chemical biology tools to understand further the downstream impact of Rce1 on Ras function and serve as potential leads for cancer therapeutics. Structure-activity relationship (SAR) analysis of a previously reported Rce1 inhibitor, NSC1011, has been performed to generate a new library of Rce1 inhibitors. The new inhibitors caused a reduction in Rce1 in vitro activity, exhibited low cell toxicity, and induced mislocalization of EGFP-Ras from the plasma membrane in human colon carcinoma cells giving rise to a phenotype similar to that observed with siRNA knockdowns of Rce1 expression. Several of the new inhibitors were more effective at mislocalizing K-Ras compared to a potent farnesyltransferase inhibitor (FTI), which is significant because of the preponderance of K-Ras mutations in cancer. (C) 2015 Elsevier Ltd. All rights reserved.
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Sc: MVol.D2, 2.5, page 14 - 24
  作者：

  DOI：——

  日期：——