4-氨基-7-甲氧基喹啉 | 103040-78-4

• 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: 4-氨基-7-甲氧基喹啉
• 英文名称: 7-methoxy-quinolin-4-ylamine
• 英文别名: 7-methoxy-[4]quinolylamine；7-Methoxy-[4]chinolylamin；4-amino-7-methoxyquinoline；7-methoxyquinolin-4-amine；4-Amino-7-methoxychinolin
• CAS: 103040-78-4
• 化学式: C₁₀H₁₀N₂O
• mdl: MFCD08063213
• 分子量: 174.202
• InChiKey: DZXVXEFSGHJKHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  48.1
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  4-氨基-7-甲氧基喹啉 、 4-二甲氨基苯异氰酸酯 以 乙酸乙酯 为溶剂， 生成 1-(4-N,N-dimethylaminophenyl)-3-(7-methoxy)quinolin-4-ylurea hydrochloride
  参考文献：
  名称：

  Phenyl urea and phenyl thiourea derivatives as HFGAN72 antagonists

  摘要：

  苯基脲和苯基硫脲衍生物的生产过程以及它们作为药物的用途被披露。

  公开号：

  US06410529B1
• 作为产物：
  描述：

  5-[(3-甲氧基苯基氨基)亚甲基]-2,2-二甲基-1,3-二噁烷-4,6-二酮 在 ammonium hydroxide 、 zinc(II) chloride 、 三氯氧磷 作用下， 以 二苯醚 为溶剂， 140.0~180.0 ℃ 、2.05 MPa 条件下， 反应 1.91h， 生成 4-氨基-7-甲氧基喹啉
  参考文献：
  名称：

  Structure–activity relationships for ferriprotoporphyrin IX association and β-hematin inhibition by 4-aminoquinolines using experimental and ab initio methods

  摘要：

  In order to probe structure-activity relationships of association with ferriprotoporphyrin IX (logK) and inhibition of beta-hematin formation, a series of 4-aminoquinolines with varying substituents at the 7-position (X) have been synthesized. These have been further elaborated by introduction of two different R groups on the 4-amino nitrogen atom in the form of methyl (R = Me) and ethylamine (R = EtNH2) side chains. Data for a previously investigated series containing an N,N-diethyl-ethylamine side chain were also compared with the findings of this study. Experimentally, logK values for the simple 4-aminoquinoline series (R = H) were found to correlate with the hydrophobicity constant (pi) of the group X. The logK values for the series with R = Me and EtNH2 were found to correlate with those of the series with R = H. The log of the 50% beta-hematin inhibitory activity (log BHIA(50)) was found to correlate with logK and either meta (sigma(m)) or para (sigma(p)) Hammett constants for the series with R = Me and EtNH2, but not the simple series with R = H. To further improve predictability, correlations with ab initio electrostatic parameters, namely Mulliken and CHelpG charges were investigated. The best correlations were found with CHelpG charges which indicated that logK values can be predicted from the charges on atom H-8 and the group X in the quinolinium species computed in vacuum, while log BHIA50 values can be predicted from the CHelpG charges on C-7, C-8 and N-1 for the neutral species in vacuum. These correlations indicate that association and inhibition of beta-hematin formation are separately determined. They also suggest that electron withdrawing groups at the 7-position, but not necessarily hydrophobic groups are required for hemozoin inhibition. The upshot is that the correlations imply that considerably more hydrophilic hemozoin inhibitors are feasible. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.040

文献信息

• Microwave-assisted synthesis of 4-quinolylhydrazines followed by nickel boride reduction: a convenient approach to 4-aminoquinolines and derivatives
  作者：Sandra Gemma、Gagan Kukreja、Pierangela Tripaldi、Maria Altarelli、Matteo Bernetti、Silvia Franceschini、Luisa Savini、Giuseppe Campiani、Caterina Fattorusso、Stefania Butini

  DOI：10.1016/j.tetlet.2008.01.128

  日期：2008.3

  Nickel(II) chloride/sodium borohydride combination was employed for the reduction of 4-hydrazinoquinoline derivatives to the corresponding anilines. This reductive protocol was efficiently applied for the reductive cleavage of monosubstituted hydrazines. We described herein the microwave-assisted synthesis of 4-hydrazinoquinolines, which furnished a high yielding and rapid two-step procedure for the

  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。
• HETEROCYCLIC COMPOUNDS AND THEIR USE AS GLYCOGEN SYNTHASE KINASE-3 INHIBITORS
  申请人：Turner Sean Colm

  公开号：US20120172376A1

  公开（公告）日：2012-07-05

  The present invention relates to novel heterocyclic compounds of formula I wherein the variables are as defined in the claims or the description, which are useful for inhibiting glycogen synthase kinase 3 (GSK-3), compositions containing the compounds, their use for preparing a medicament for the treatment of a medical disorder susceptible to the treatment with a compound that modulates, preferably inhibits, the activity of glycogen synthase kinase 3β, and methods of treatment of medical disorders susceptible to treatment with a compound that modulates glycogen synthase kinase 3β activity using the compounds.

  本发明涉及式I的新颖杂环化合物，其中变量如权利要求或说明书中所定义，这些化合物可用于抑制糖原合酶激酶3（GSK-3），包含这些化合物的组合物，以及使用这些化合物制备用于治疗对调节、优选抑制GSK-3β活性化合物敏感的医疗病症的药物的用途，以及使用这些化合物治疗对调节GSK-3β活性化合物敏感的医疗病症的方法。
• Nitrogen-Containing heterocyclyl ketones and methods of use
  申请人：Albrecht Brian K.

  公开号：US20080280917A1

  公开（公告）日：2008-11-13

  Selected compounds are effective for prophylaxis and treatment of diseases, such as HGF mediated diseases. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable salts thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving, cancer and the like. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.

  所选化合物对于预防和治疗HGF介导的疾病等疾病有效。本发明涵盖了新型化合物、类似物、前药和其药学上可接受的盐、制药组合物以及预防和治疗涉及癌症等疾病和其他疾病或病况的方法。本发明还涉及制造这种化合物的过程，以及在这些过程中有用的中间体。
• Nitrogen-containing heterocyclyl ketones and methods of use
  申请人：Amgen Inc.

  公开号：US08314087B2

  公开（公告）日：2012-11-20

  Selected compounds are effective for prophylaxis and treatment of diseases, such as HGF mediated diseases. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable salts thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving, cancer and the like. The subject invention also relates to processes for making such compounds as well as to intermediates useful in such processes.

  所选化合物对于预防和治疗诸如HGF介导的疾病等疾病有效。本发明涵盖了新型化合物、类似物、前药及其药学上可接受的盐、制药组合物和预防和治疗涉及癌症等疾病和其他疾病或状况的方法。本发明还涉及制备这种化合物的过程以及在这种过程中有用的中间体。
• 1-(QUINOLIN-4-YL)-3-(6-(TRIFLUOROMETHYL)-PYRIDIN-2-YL)UREA AND 1-(QUINOLIN-4-YL)-3-(6-(TRIFLUOROMETHYL)-PYRAZINE-2-YL)UREA DERIVATIVES AS GLYCOGEN SYNTHASE KINASE 3 (GSK-3) INHIBITORS FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES
  申请人：AbbVie Deutschland GmbH & Co. KG

  公开号：EP3351543A1

  公开（公告）日：2018-07-25

  The present invention relates to 1-(quinolin-4-yl)-3-(6-(trifluoromethyl)-pyridin-2-y)urea and 1-(quinolin-4-yl)-3-(6-(trifluoromethyl)-pyrazine-2-yl) urea derivates of formula (I-2): as glycogen synthase kinase 3 (GSK-3) for treating e.g. schizophrenia, Alzheimer's disease, behavioural and psychiatric symptoms of dementia, Parkinson's disease, tauopathies, vascular dementia, acute stroke and other traumatic injuries, cerebrovascular accidents, brain and spinal cord trauma, peripheral neuropathies, bipolar disorders, retinopathies, glaucoma, pain, rheumatoid arthritis and osteoarthritis. A preferred example is e.g. 1-(quinolin-4-yl)-3-(6-(trifluoromethyl)-pyridin-2-yl)urea.

  本发明涉及式 (I-2) 的 1-(喹啉-4-基)-3-(6-(三氟甲基)-吡啶-2-基)脲和 1-(喹啉-4-基)-3-(6-(三氟甲基)-吡嗪-2-基)脲衍生物： 作为糖原合酶激酶 3（GSK-3）用于治疗精神分裂症、阿尔茨海默病、痴呆的行为和精神症状、帕金森病、陶氏病、血管性痴呆、急性中风和其他外伤、脑血管意外、脑和脊髓创伤、周围神经病、双相情感障碍、视网膜病变、青光眼、疼痛、类风湿性关节炎和骨关节炎等。一个优选的例子是 1-(喹啉-4-基)-3-(6-(三氟甲基)-吡啶-2-基)脲。