7-methoxy-2-methylquinolin-4-ol | 58596-43-3

• 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: 7-methoxy-2-methylquinolin-4-ol
• 英文别名: 7-methoxy-2-methyl-quinolin-4-ol；7-Methoxy-2-methyl-chinolin-4-ol；4-Hydroxy-2-methyl-7-methoxy-chinolin；4-Hydroxy-7-methoxy-2-methylchinolin；7-methoxy-2-methyl-1H-quinolin-4-one
• CAS: 58596-43-3
• 化学式: C₁₁H₁₁NO₂
• mdl: MFCD00086643
• 分子量: 189.214
• InChiKey: VXLZVELXYBOECH-UHFFFAOYSA-N

物化性质

• 熔点：
  249-250 °C(Solv: methanol (67-56-1))
• 沸点：
  324.9±42.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-methoxy-2-methylquinolin-4-ol 在 碘 、 乙酸酐 、 三氯氧磷 作用下， 以 甲醇 、 苯 为溶剂， 反应 20.0h， 生成 12-Chloro-9-methoxy-benzo[a]acridine
  参考文献：
  名称：

  Jayabalan; Shanmugam, Synthesis, 1991, # 3, p. 217 - 220

  摘要：

  DOI：
• 作为产物：
  描述：

  间氨基苯甲醚 在 盐酸 、 二苯醚 作用下， 生成 7-methoxy-2-methylquinolin-4-ol
  参考文献：
  名称：

  Leonard; Herbrandson; Van Heyningen, Journal of the American Chemical Society, 1946, vol. 68, p. 1281

  摘要：

  DOI：

文献信息

• Two-Photon Excitable Photoremovable Protecting Groups Based on the Quinoline Scaffold for Use in Biology
  作者：Anna-Lisa K. Hennig、Davide Deodato、Naeem Asad、Cyril Herbivo、Timothy M. Dore

  DOI：10.1021/acs.joc.9b02780

  日期：2020.1.17

  Photoremovable protecting groups (PPGs) are powerful tools for physiological studies, harnessing light as an on/off switch to provide tight spatio-temporal control over the release of biological effectors through two-photon excitation (2PE) in tissue culture and whole-animal studies. We carried out a series of systematic structural modifications to the (8-cyano-7-hydroxyquinolin-2-yl)methyl (CyHQ)

  可光除去的保护基团（PPG）是用于生理学研究的强大工具，利用光作为开/关开关，通过组织培养和全动物研究中的双光子激发（2PE）对生物效应物的释放提供严格的时空控制。我们对（8-cyano-7-hydroxyquinolin-2-yl）methyl（CyHQ）生色团进行了一系列系统的结构修饰，以进行SAR研究，目的是增强其光化学性质，特别是其双光子解笼作用横截面（δu）。当在C4位置添加取代基时，可获得最佳结果，这可将δu提高释放乙酸盐的7倍，同时保留了CyHQ PPG的所有其他优异性能，包括高量子产率（Φu），低易感性在黑暗中自发水解，和良好的水溶性 Hammett相关分析表明，C4处的富电子取代基有利于光解效率，从而为光解反应的机理提供了重要的见识。在模拟的生理条件下，使用了四种最佳的CyHQ衍生物以高产率介导了高哌酸的有效释放。我们的努力导致了对2PE敏感的PPG的开发，其具有显着的δu值（高达2
• [EN] TRICYCLIC PIPERIDINE COMPOUNDS<br/>[FR] COMPOSÉS PIPÉRIDINIQUES TRICYCLIQUES
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：WO2015075023A1

  公开（公告）日：2015-05-28

  The present invention relates to compounds of the formula (I), wherein R, R1a, R1b, R2, R3, and X are as described in the description, to their preparation, to pharmaceutically acceptable salts thereof, and to their use as pharmaceuticals, to pharmaceutical compositions containing one or more compounds of formula (I), to methods for the preparation of such compounds of formula (I), and especially to their use as TPH modulators.

  本发明涉及公式（I）的化合物，其中R、R1a、R1b、R2、R3和X如描述中所述，以及它们的制备方法，其药用盐，以及它们作为药物的用途，包括含有一个或多个公式（I）化合物的药物组合物，以及制备这种公式（I）化合物的方法，特别是它们作为TPH调节剂的用途。
• TRICYCLIC PIPERIDINE COMPOUNDS
  申请人：ACTELION PHARMACEUTICALS LTD

  公开号：US20160272655A1

  公开（公告）日：2016-09-22

  The present invention relates to compounds of the formula (I) wherein R, R 1a , R 1b , R 2 , R 3 , and X are as described in the description, to their preparation, to pharmaceutically acceptable salts thereof, and to their use as pharmaceuticals, to pharmaceutical compositions containing one or more compounds of formula (I), to methods for the preparation of such compounds of formula (I), and especially to their use as TPH modulators.

  本发明涉及式（I）的化合物，其中R、R1a、R1b、R2、R3和X如描述中所述，其制备方法，其药学上可接受的盐以及它们作为药物的用途，含有一个或多个式（I）化合物的药物组合物，制备这种式（I）化合物的方法，特别是它们作为TPH调节剂的用途。
• Searching for New Leads for Tuberculosis: Design, Synthesis, and Biological Evaluation of Novel 2-Quinolin-4-yloxyacetamides
  作者：Eleni Pitta、Maciej K. Rogacki、Olga Balabon、Sophie Huss、Fraser Cunningham、Eva Maria Lopez-Roman、Jurgen Joossens、Koen Augustyns、Lluis Ballell、Robert H. Bates、Pieter Van der Veken

  DOI：10.1021/acs.jmedchem.6b00245

  日期：2016.7.28

  In this study, a new series of more than 60 quinoline derivatives has been synthesized and evaluated against Mycobacterium tuberculosis (H37Rv). Apart from the SAR exploration around the initial hits, the optimization process focused on the improvement of the physicochemical properties, cytotoxicity, and metabolic stability of the series. The best compounds obtained exhibited MIC values in the low micromolar range, excellent intracellular antimycobacterial activity, and an improved physicochemical profile without cytotoxic effects. Further investigation revealed that the amide bond was the source for the poor blood stability observed, while some of the compounds exhibited hERG affinity. Compound 83 which contains a benzoxazole ring instead of the amide group was found to be a good alternative, with good blood stability and no hERG affinity, providing new opportunities for the series. Overall, the obtained results suggest that further optimization of solubility and microsomal stability of the series could provide a strong lead for a new anti-TB drug development program.
• Salzer et al., Chemische Berichte, 1948, vol. 81, p. 12,17
  作者：Salzer et al.

  DOI：——

  日期：——