3,4-dimethyl-7-aminoquinolin-2-one | 19841-01-1

• 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: 3,4-dimethyl-7-aminoquinolin-2-one
• 英文别名: 7-amino-3,4-dimethyl-1H-quinolin-2-one；7-amino-3,4-dimethyl-1H-quinolin-2-one
• CAS: 19841-01-1
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: SFYRLVFQHRZDCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-dimethyl-7-aminoquinolin-2-one 在 氢氧化钾 、 硫酸 、 溴 、 sodium acetate 、 potassium carbonate 、 溶剂黄146 、 N,N-二乙基苯胺 、 sodium nitrite 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 1.0h， 生成 2,5,6-trimethyl-9-methoxypyrrolo<3,2,1-ij>quinolin-4-one
  参考文献：
  名称：

  New synthesis of pyrrolo [3,2,1-ij] quinolin-4-one derivatives

  摘要：

  A new convenient synthesis of pyrrolo[3,2,1-ij]quinolin-4-one derivatives is described. In this method, methyl-7-hydroxquinoline-2-ones are the starting materials onto which the third pyrrolo ring is condensed directly, yielding dehydrogenated methyl-9-hydroxypyrrolo[3,2,1-ij]quinolin-4-ones.

  DOI：

  10.1021/jo00003a016
• 作为产物：
  描述：

  间苯二胺 、 2-甲基乙酰乙酸乙酯 反应 48.0h， 生成 3,4-dimethyl-7-aminoquinolin-2-one
  参考文献：
  名称：

  包含二硫代氨基甲酸酯部分作为多功能AChE抑制剂的喹啉酮衍生物的设计，合成和评估，用于治疗阿尔茨海默氏病

  摘要：

  抽象的 设计并合成了一系列带有二硫代氨基甲酸酯部分的新型喹啉酮衍生物，作为用于治疗AD的多功能AChE抑制剂。这些化合物中的大多数对ee AChE表现出强烈而明显的选择性抑制。其中，化合物4c中被确定为最有效的抑制剂既EE乙酰胆碱酯酶和ħ胆碱酯酶（IC 50 = 0.22μM为eeAChE; IC 50 = 0.16μM为ħ乙酰胆碱酯酶），它也是对乙酰胆碱酯酶诱导的Aβ的最佳抑制剂聚集（在100μM时为29.02％）和有效的自诱导Aβ聚集抑制剂（在25μM时为30.67％）。动力学和分子建模研究表明，化合物4c是一种混合型抑制剂，可以同时与AChE的催化阴离子位点（CAS）和外围阴离子位点（PAS）相互作用。此外，4c具有良好的穿过BBB的能力，对SH-SY5Y神经母细胞瘤细胞无毒性，并且在高达2500 mg / kg（po）的剂量下对小鼠具有良好的耐受性。

  DOI：

  10.1080/14756366.2019.1687460

文献信息

• [EN] QUINOLONES AS INHIBITORS OF CLASS IV BROMODOMAIN PROTEINS<br/>[FR] QUINOLONES À TITRE D'INHIBITEURS DE PROTÉINES À BROMODOMAINES DE CLASSE IV
  申请人：UCL BUSINESS PLC

  公开号：WO2016034512A1

  公开（公告）日：2016-03-10

  The present invention provides compounds of formula (I) as described herein and pharmaceutically acceptable salts, hydrates and solvates thereof for use in medicine, for example in the treatment of acute myeloid leukaemia:

  本发明提供了如下所述的化合物(I)及其药用可接受的盐、水合物和溶剂合物，用于医学上的应用，例如用于治疗急性髓样白血病：
• Photophysics of Coumarin and Carbostyril-Sensitized Luminescent Lanthanide Complexes: Implications for Complex Design in Multiplex Detection
  作者：Daniel Kovacs、Xi Lu、Lívia S. Mészáros、Marjam Ott、Julien Andres、K. Eszter Borbas

  DOI：10.1021/jacs.6b11274

  日期：2017.4.26

  Luminescent lanthanide (Ln(III)) complexes with coumarin or carbostyril antennae were synthesized and their photophysical properties evaluated using steady-state and time-resolved UV-vis spectroscopy. Ligands bearing distant hydroxycoumarin-derived antennae attached through triazole linkers were modest sensitizers for Eu(III) and Tb(III), whereas ligands with 7-amidocarbostyrils directly linked to the coordination site could reach good quantum yields for multiple Ln(III), including the visible emitters Sm(III) and Dy(III), and the near-infrared emitters Nd(III) and Yb(III). The highest lanthanide-centered luminescence quantum yields were 35% (Tb), 7.9% (Eu), 0.67% (Dy), and 0.18% (Sm). Antennae providing similar luminescence intensities with 2-4 Ln-emitters were identified. Photoredox quenching of the carbostyril antenna excited states was observed for all Eu(III)-complexes and should be sensitizing in the case of Yb(III); the scope of the process extends to Ln(III) for which it has not been seen previously, specifically Dy(III) and Sm(III). The proposed process is supported by photophysical and electrochemical data. A FRET-type mechanism was identified in architectures with both distant and close antennae for all of the Lns. This mechanism seems to be the only sensitizing one at long distance and probably contributes to the sensitization at shorter distances along with the triplet pathway. The complexes were nontoxic to either bacterial or mammalian cells. Complexes of an ester-functionalized ligand were taken up by bacteria in a concentration-dependent manner. Our results suggest that the effects of FRET and photoredox quenching should be taken into consideration when designing luminescent Ln complexes. These results also establish these Ln(III)-complexes for multiplex detection beyond the available two-color systems.
• CHILIN, A.;RODIGHIERO, P.;PASTORINI, G.;GUIOTTO, A., J. ORG. CHEM., 56,(1991) N, C. 980-983
  作者：CHILIN, A.、RODIGHIERO, P.、PASTORINI, G.、GUIOTTO, A.

  DOI：——

  日期：——
• QUINOLONES AS INHIBITORS OF CLASS IV BROMODOMAIN PROTEINS
  申请人：UCL BUSINESS PLC

  公开号：US20170291875A1

  公开（公告）日：2017-10-12

  The present invention provides compounds of formula (I) as described herein and pharmaceutically acceptable salts, hydrates and solvates thereof for use in medicine, for example in the treatment of acute myeloid leukaemia:
• Design, synthesis and evaluation of quinolinone derivatives containing dithiocarbamate moiety as multifunctional AChE inhibitors for the treatment of Alzheimer’s disease
  作者：Jie Fu、Fengqi Bao、Min Gu、Jing Liu、Zhipeng Zhang、Jiaoli Ding、Sai-Sai Xie、Jinsong Ding

  DOI：10.1080/14756366.2019.1687460

  日期：2020.1.1

  Abstract A series of novel quinolinone derivatives bearing dithiocarbamate moiety were designed and synthesised as multifunctional AChE inhibitors for the treatment of AD. Most of these compounds exhibited strong and clearly selective inhibition to eeAChE. Among them, compound 4c was identified as the most potent inhibitor to both eeAChE and hAChE (IC50 = 0.22 μM for eeAChE; IC50 = 0.16 μM for hAChE)

  抽象的 设计并合成了一系列带有二硫代氨基甲酸酯部分的新型喹啉酮衍生物，作为用于治疗AD的多功能AChE抑制剂。这些化合物中的大多数对ee AChE表现出强烈而明显的选择性抑制。其中，化合物4c中被确定为最有效的抑制剂既EE乙酰胆碱酯酶和ħ胆碱酯酶（IC 50 = 0.22μM为eeAChE; IC 50 = 0.16μM为ħ乙酰胆碱酯酶），它也是对乙酰胆碱酯酶诱导的Aβ的最佳抑制剂聚集（在100μM时为29.02％）和有效的自诱导Aβ聚集抑制剂（在25μM时为30.67％）。动力学和分子建模研究表明，化合物4c是一种混合型抑制剂，可以同时与AChE的催化阴离子位点（CAS）和外围阴离子位点（PAS）相互作用。此外，4c具有良好的穿过BBB的能力，对SH-SY5Y神经母细胞瘤细胞无毒性，并且在高达2500 mg / kg（po）的剂量下对小鼠具有良好的耐受性。