4-氨基-6-甲氧基-2-甲基喹啉 | 104217-23-4

• 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: 4-氨基-6-甲氧基-2-甲基喹啉
• 英文名称: 2-methyl-6-methoxy-4-aminoquinoline
• 英文别名: 6-methoxy-2-methyl-4-quinolinamine；6-methoxy-2-methylquinolin-4-amine；6-methoxy-2-methyl-[4]quinolylamine；6-Methoxy-2-methyl-[4]chinolylamin
• CAS: 104217-23-4
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: KLQQFYUSSBAOFT-UHFFFAOYSA-N

物化性质

• 熔点：
  211-213 °C
• 沸点：
  366.0±37.0 °C(Predicted)
• 密度：
  1.181±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：
  0.18
• 拓扑面积：
  48.1
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933499090
• WGK Germany：
  3
• 危险标志：
  GHS05,GHS07
• 危险性描述：
  H302,H318
• 危险性防范说明：
  P280,P305 + P351 + P338

反应信息

• 作为反应物：
  描述：

  4-氨基-6-甲氧基-2-甲基喹啉 在 碘 、 碳酸氢钠 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 26.0h， 生成 2-(5-diethylaminomethyl-2-oxo-oxazolidin-3-yl)-N-(6-methoxy-2-methylquinolin-4-yl)acetamide
  参考文献：
  名称：

  Design, synthesis and docking studies of quinoline-oxazolidinone hybrid molecules and their antitubercular properties

  摘要：

  New series of quinoline-oxazolidinone hybrid molecules were synthesized based on the preliminary docking studies. All the newly synthesized compounds were characterized by spectral analyses. The newly synthesized compounds were screened for their antimycobacterial properties based on the promising preliminary antibacterial screening results. Amongst tested compounds, compounds 8a, 8j and 13a were active at 0.65 mu g/mL against Mycobacterium tuberculosis H(37)Rv strain. The mode of action of these active compounds was carried out by docking of receptor enoyl-ACP reductase with newly synthesized candidate ligands 8a, 8j and 13a. These compounds exhibited well established bonds with one or more amino acids in the receptor active pocket. From the docking studies, compound 8j was considered to be the best inhibitor. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.049
• 作为产物：
  描述：

  4-肼基-6-甲氧基-2-甲基喹啉 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以79%的产率得到4-氨基-6-甲氧基-2-甲基喹啉
  参考文献：
  名称：

  微波辅助合成4-喹啉基肼，然后还原硼化镍：一种方便的制备4-氨基喹啉及其衍生物的方法

  摘要：

  氯化镍（II）/硼氢化钠组合用于将4-肼基喹啉衍生物还原为相应的苯胺。该还原方案被有效地应用于单取代肼的还原裂解。我们在本文中描述了4-肼基喹啉的微波辅助合成，其提供了高产率和快速的两步法，用于在温和条件下合成4-氨基喹啉作为抗疟原体。

  DOI：

  10.1016/j.tetlet.2008.01.128

文献信息

• METHOD OF IMPROVING STABILITY OF SWEET ENHANCER AND COMPOSITION CONTAINING STABILIZED SWEET ENHANCER
  申请人：TACHDJIAN Catherine

  公开号：US20120041078A1

  公开（公告）日：2012-02-16

  The present invention includes methods of stabilizing one or more sweet enhancers when they are exposed to a light source as well as liquid compositions containing one or more sweet enhancers and one or more photostabilizers.

  本发明包括在甜味增强剂暴露于光源时稳定一个或多个甜味增强剂的方法，以及包含一个或多个甜味增强剂和一个或多个光稳定剂的液体组合物。
• SWEET FLAVOR MODIFIER
  申请人：TACHDJIAN Catherine

  公开号：US20110245353A1

  公开（公告）日：2011-10-06

  The present invention includes compounds having structural formula (I), or pharmaceutically acceptable salts, solvate, and/or ester thereof. These compounds are useful as sweet flavor modifiers. The present invention also includes compositions comprising the present compounds and methods of enhancing the sweet taste of ingestible compositions. Furthermore, the present invention provides methods for preparing the compounds.

  本发明包括具有结构式(I)的化合物，或其药用可接受的盐、溶剂合物和/或酯。这些化合物可用作甜味调节剂。本发明还包括包含本发明的化合物的组合物以及增强可食用组合物甜味的方法。此外，本发明提供了制备这些化合物的方法。
• New insights into the SAR and drug combination synergy of 2-(quinolin-4-yloxy)acetamides against Mycobacterium tuberculosis
  作者：Bruno Couto Giacobbo、Kenia Pissinate、Valnês Rodrigues-Junior、Anne Drumond Villela、Estêvão Silveira Grams、Bruno Lopes Abbadi、Fernanda Teixeira Subtil、Nathalia Sperotto、Rogério Valim Trindade、Davi Fernando Back、Maria Martha Campos、Luiz Augusto Basso、Pablo Machado、Diógenes Santiago Santos

  DOI：10.1016/j.ejmech.2016.11.048

  日期：2017.1

  2-(Quinolin-4-yloxy)acetamides have been described as potent and selective in vitro inhibitors of Mycobacterium tuberculosis (Mtb) growth. Herein, a new series of optimized compounds were found to demonstrate highly potent antitubercular activity, with minimum inhibitory concentration (MIC) values against drug-susceptible and drug-resistant Mycobacterium tuberculosis strains in the submicromolar range

  2-（喹啉-4-基氧基）乙酰胺已被描述为结核分枝杆菌（Mtb）生长的有效和选择性体外抑制剂。在此，发现了一系列新的优化化合物，它们显示出强大的抗结核活性，并且对药物敏感性和耐药性结核分枝杆菌的抑菌浓度（MIC）值最小。亚微摩尔范围内的菌株。此外，最具活性的化合物对哺乳动物细胞没有明显的毒性，并且在Mtb感染的巨噬细胞模型中显示出与异烟肼和利福平相似的细胞内活性。使用棋盘法研究铅化合物与一线和二线抗结核药物的缔合谱表明，2-（喹啉-4-基氧基）乙酰胺与利福平具有协同作用。最终，一些合成化合物显示出良好的渗透性，适度的新陈代谢速率和较低的药物-药物相互作用风险，表明2-（喹啉-4-基氧基）乙酰胺可能为用于开发新的替代疗法的候选药物。结核病的治疗。
• The Effects of Membership in Church-Related Associations and Labor Unions on Age Differences in Voluntary Association Affiliations
  作者：Jon Hendricks、Stephen J. Cutler

  DOI：10.1093/geront/41.2.250

  日期：2001.4.1

  Purpose:When compositional differences between age groups are controlled, the bivariate, curvilinear pattern of age differences in voluntary association memberships is replaced by one in which peak membership levels occur in late middle age and remain relatively stable thereafter. We sought to determine if this adjusted pattern persists when widespread memberships in two types of associations are removed: (1) church-related organizations, in which membership increases with age but may be confounded with church membership per se; and (2) labor unions, in which membership is also widespread but may not be "voluntary."Design and Methods:Total memberships in 14 types of associations were examined using aggregated data from 12 national surveys conducted between 1974 and 1994.Results:The familiar curvilinear relationship at the bivariate level appears, but in the multivariate analysis, membership levels rise from ages 18–24 through 55–59 and persist close to that level through ages 85 and older.Implications:The results reaffirm that age differences in voluntary association affiliations are due to age-based compositional differences; they also show, however, that the pattern observed with controls is neither driven by membership in church-related "associations" nor altered when membership in labor unions is excluded.

  目的：当年龄组之间的构成差异受到控制时，自愿协会会员资格中年龄差异的二元曲线模式将被一种会员水平峰值出现在中年后期并在此后保持相对稳定的模式所取代。我们试图确定当两类协会的广泛会员资格被取消时，这种调整后的模式是否仍然存在：（1）与教会相关的组织，其中会员资格随着年龄的增长而增加，但可能与教会会员资格本身相混淆； (2) 工会，其成员资格也很广泛，但可能不是“自愿的”。 设计和方法：使用 1974 年至 1994 年间进行的 12 次全国性调查的汇总数据对 14 类协会的总成员资格进行了审查。双变量水平上出现了熟悉的曲线关系，但在多变量分析中，会员水平从 18-24 岁上升到 55-59 岁，并在 85 岁及以上一直保持接近该水平。 意义：结果再次证实，自愿协会中的年龄差异隶属关系是由于年龄构成差异造成的；然而，它们也表明，通过控制观察到的模式既不是由与教会有关的"协会"的成员资格所驱动的，也不是因为工会成员资格被排除在外而改变的。
• 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.