1-[(氨基氧基)甲基]-3-甲氧基苯 | 15256-05-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-[(氨基氧基)甲基]-3-甲氧基苯
• 英文名称: 1-[(aminooxy)methyl]-3-methoxybenzene
• 英文别名: O-(3-methoxybenzyl)hydroxylamine；O-<3-Methoxy-benzyl>-hydroxylamin；O-(3-Methoxy-benzyl)-hydroxylamin；3-Methoxybenzyloxyamin；O-[(3-methoxyphenyl)methyl]hydroxylamine
• CAS: 15256-05-0
• 化学式: C₈H₁₁NO₂
• 分子量: 153.181
• InChiKey: KBXVIQKLRHKPEJ-UHFFFAOYSA-N

物化性质

• 沸点：
  286.0±23.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(氨基氧基)甲基]-3-甲氧基苯 在 碳酸氢钠 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N-(2-Amino-ethyl)-O-(3-methoxy-benzyl)-hydroxylamine
  参考文献：
  名称：

  1-Benzyloxy-4,5-dihydro-1H-imidazol-2-yl-amines, a novel class of NR1/2B subtype selective NMDA receptor antagonists

  摘要：

  Screening of the Roche compound depository led to the identification of (1-benzyloxy-4,5-dihydro-1H-imidazol-2-yl)-butyl amine 4, a structurally novel NR1/2B Subtype selective NMDA receptor antagonist. The structure-activity relationships developed in this series resulted in the discovery of a novel class of potent and selective NMDA receptor blockers displaying activity in vivo. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00713-3
• 作为产物：
  描述：

  3-甲氧基氯苄 生成 1-[(氨基氧基)甲基]-3-甲氧基苯
  参考文献：
  名称：

  羟胺衍生物的合成具有降胆固醇的活性。

  摘要：

  DOI：

  10.1021/jm00316a012

文献信息

• Synthesis, in Vitro Antimycobacterial and Antibacterial Evaluation of IMB-070593 Derivatives Containing a Substituted Benzyloxime Moiety
  作者：Zengquan Wei、Jian Wang、Mingliang Liu、Sujie Li、Lanying Sun、Huiyuan Guo、Bin Wang、Yu Lu

  DOI：10.3390/molecules18043872

  日期：——

  A series of novel IMB-070593 derivatives containing a substituted benzyloxime moiety and displaying a remarkable improvement in lipophilicity were synthesized and evaluated for their in vitro antimycobacterial and antibacterial activity. Our results reveal that the target compounds 19a–m have considerable Gram-positive activity (MIC: <0.008–32 µg/mL), although they are generally less active than the reference drugs against the Gram-negative strains. In particular, compounds 19h, 19j, 19k and 19m show good activity (MICs: <0.008–4 µg/mL) against all of the tested Gram-positive strains, including ciprofloxacin (CPFX)- and/or levofloxacin (LVFX)-resistant MSSA, MRSA and MSSE. Moreover, compound 19l (MIC: 0.125 µg/mL) is found to be 2–4 fold more active than the parent IMB070593, CPFX and LVFX against M. tuberculosis H37Rv ATCC 27294.

  合成并评价了一系列含有取代苯甲酰肟基团且脂溶性显著提高的新型IMB-070593衍生物的体外抗分枝杆菌和抗菌活性。我们的结果显示，目标化合物19a–m对革兰氏阳性菌具有相当高的活性（MIC：<0.008–32 µg/mL），尽管它们对革兰氏阴性菌的活性通常低于参考药物。特别是化合物19h、19j、19k和19m对所有测试的革兰氏阳性菌株显示出良好的活性（MICs：<0.008–4 µg/mL），包括对环丙沙星（CPFX）和/或左氧氟沙星（LVFX）耐药的甲氧西林敏感金黄色葡萄球菌（MSSA）、甲氧西林耐药金黄色葡萄球菌（MRSA）和表皮葡萄球菌（MSSE）。此外，化合物19l（MIC：0.125 µg/mL）对抗ATCC 27294的结核杆菌H37Rv的活性是母体化合物IMB070593、环丙沙星和左氧氟沙星的2–4倍。
• [EN] PHARMACEUTICAL COMBINATION<br/>[FR] COMBINAISON PHARMACEUTIQUE
  申请人：ASTRAZENECA AB

  公开号：WO2003101956A1

  公开（公告）日：2003-12-11

  There is provided a combination product comprising: (1) a compound of claim 1 in WO 02/44145 or a compound of claim 20 in WO 02/44145 (or derivative thereof)or a pharmaceutically-acceptable derivative thereof; and (1) a compound as defined in claim 1 of WO 01/28992 or (2) a compound of Claim 34 of WO 01/28992 or (3) Compound A or B or C or D (or pharmaceutically-acceptable salts thereof) for use in treating arrhythmia or a coagulation controlled complication thereof.

  提供了一种组合产品，包括：(1) WO 02/44145中权利要求1的化合物或WO 02/44145中权利要求20的化合物（或其衍生物）或药用可接受的衍生物；以及（1）WO 01/28992中权利要求1定义的化合物或（2）WO 01/28992中权利要求34的化合物或（3）化合物A或B或C或D（或药用可接受的盐）用于治疗心律不齐或其凝血控制的并发症。
• Transformation of masked benzyl alcohols to o-aminobenzaldehydes through C–H activation: a facile approach to quinazolines
  作者：Xiaolan Chen、Jian Han、Yan Zhu、Chunchen Yuan、Jingyu Zhang、Yingsheng Zhao

  DOI：10.1039/c6cc05560e

  日期：——

  Direct Transformation of directing group to important synthetic units would provide a high atom efficiency synthetic approach in synthetic chemistry. Herein, a convenient protocol in synthesis of o-aminobenzaldehyde and benzoxazole...

  指导基团直接转化为重要的合成单元将为合成化学提供一种高原子效率的合成方法。此处是合成邻氨基苯甲醛和苯并恶唑的便捷方法...
• Substituted aryl and heteroaryl derivatives, the preparation thereof and the use therof as pharmaceutical compositions
  申请人：Boehringer Ingelheim Pharma KG

  公开号：US20030045712A1

  公开（公告）日：2003-03-06

  The present invention relates to new substituted aryl and heteroaryl derivatives of general formula 1 wherein A, Ar, n, X, Y 1 , Y 2 , Y 3 , Y 4 , R 1 and R 5 are defined as in claim 1 , the prodrugs, the tautomers, stereoisomers, mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases which have valuable properties. Thus, the compounds of the above general formula I wherein R 5 does not contain a cyano group have, in particular, an antithrombotic effect and a selective factor Xa-inhibiting effect with generally improved compatibility. The compounds of the above general formula I wherein R 5 contains a cyano group are valuable intermediate products for preparing the antithrombotic compounds of general formula I.

  本发明涉及一种新的取代芳基和杂环芳基衍生物，其一般化学式为1，其中A、Ar、n、X、Y1、Y2、Y3、Y4、R1和R5如权利要求书中定义，其前药、互变异构体、立体异构体、它们的混合物及其盐，特别是其与具有有价值性能的无机或有机酸或碱的生理可接受的盐。因此，上述一般式I中的化合物，其中R5不含氰基，具有特别的抗血栓作用和选择性因子Xa抑制作用，并且通常具有改进的相容性。上述一般式I中的化合物，其中R5含有氰基，是制备一般式I抗血栓化合物的有价值的中间体。
• Design, Synthesis, Molecular Docking and Biological Evaluation of Novel Coumarin-Oxime Ether Derivatives as COX-2 Inhibitors
  作者：M. Vijaya Bhargavi、P. Shashikala、M. Sumakanth、Shravan Kumar Gunda

  DOI：10.14233/ajchem.2017.20865

  日期：——

  Coumarin-oxime ether derivatives (14-25) were synthesized by an efficient and straight forward procedure from the reaction of 3-acetyl coumarin (1) and o-substituted benzyl hydroxyl amines (2-13) in pyridinium p-toluenesulfonate/dichloromethane (PPTS/DCM) at reflux temperature. High yields and simple operations are important features of this methodology. The method is very useful for the construction of many biologically active oxime ether derivatives. The structures of the synthesized compounds are established based on IR, NMR and MASS spectrometry. Molecular docking studies were performed against selective COX-2 enzyme using Discovery Studio v3.5. The compounds with good LibDock score were screened for their in vivo anti-inflammatory activity by paw edema method, employing indomethacin as a reference standard.

  香豆素-肟醚衍生物（14-25）是由 3-乙酰基香豆素（1）和邻取代苄基羟胺（2-13）在吡啶对甲苯磺酸盐/二氯甲烷（PPTS/DCM）中于回流温度下反应合成的，该过程高效且简单。产量高、操作简单是该方法的重要特点。该方法非常适用于制造许多具有生物活性的肟醚衍生物。根据红外光谱、核磁共振和质谱分析，确定了合成化合物的结构。使用 Discovery Studio v3.5 针对选择性 COX-2 酶进行了分子对接研究。以吲哚美辛为参考标准，采用爪水肿法对 LibDock 得分较高的化合物进行了体内抗炎活性筛选。