4-乙氧基-N-羟基苯胺 | 49773-26-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4-乙氧基-N-羟基苯胺
• 英文名称: 4-ethoxy-N′-hydroxybenzimidamide
• 英文别名: 4-Ethoxy-N-hydroxy-benzamidine；4-ethoxy-N'-hydroxybenzenecarboximidamide
• CAS: 49773-26-4
• 化学式: C₉H₁₂N₂O₂
• 分子量: 180.206
• InChiKey: ABFQINNISSWOAX-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：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-乙氧基-N-羟基苯胺 在 sodium methylate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 生成 1-(3-(5-amino-4-(3-(4-ethoxyphenyl)-1,2,4-oxadiazol-5-yl)-1H-1,2,3-triazol-1-yl)phenyl)ethan-1-one oxime
  参考文献：
  名称：

  Small Molecule Inhibition of MicroRNA miR-21 Rescues Chemosensitivity of Renal-Cell Carcinoma to Topotecan

  摘要：

  Chemical probes of microRNA (miRNA) function are potential tools for understanding miRNA biology that also provide new approaches for discovering therapeutics for miRNA-associated diseases. MicroRNA-21 (miR-21) is an oncogenic miRNA that is overexpressed in most cancers and has been strongly associated with driving chemoresistance in cancers such as renal cell carcinoma (RCC). Using a cell-based luciferase reporter assay to screen small molecules, we identified a novel inhibitor of miR-21 function. Following structure-activity relationship studies, an optimized lead compound demonstrated cytotoxicity in several cancer cell lines. In a chemoresistant-RCC cell line, inhibition of miR-21 via small molecule treatment rescued the expression of tumor-suppressor proteins and sensitized cells to topotecan-induced apoptosis. This resulted in a > 10-fold improvement in topotecan activity in cell viability and clonogenic assays. Overall, this work reports a novel small molecule inhibitor for perturbing miR-21 function and demonstrates an approach to enhancing the potency of chemotherapeutics specifically for cancers derived from oncomir addiction.

  DOI：

  10.1021/acs.jmedchem.7b01891
• 作为产物：
  描述：

  对乙氧基苯腈 在 盐酸羟胺 、 sodium carbonate 作用下， 生成 4-乙氧基-N-羟基苯胺
  参考文献：
  名称：

  取代的 1,2,4-恶二唑类似物的设计、微波辅助合成和表征作为有前景的药理学药物

  摘要：

  恶二唑分子支架具有多种药理活性，例如镇咳、麻醉 [1]、驱虫 [2]、抗 HIV [3]、抗过敏 [4]、抗癌 [5]、抗惊厥 [6]、抗炎 [...] 7]、抗菌[8]、抗血小板、抗血栓形成[9]、杀虫[10]、单胺氧化酶抑制[11]、毒蕈碱受体激动剂[12]和选择性H3受体拮抗剂[13]等特性。受到这些观察结果的鼓舞，并继续我们关于合成具有药理特性的新型杂环化合物 [14-17] 和筛选杂环化合物 [18-20] 的多晶型特性的研究工作，我们决定将二苯甲酮部分加入到1,2,4-恶二唑核（Scheme-I）在微波方法的支持下研究产率和总反应时间。

  DOI：

  10.14233/ajchem.2017.20626

文献信息

• <i>In vitro</i> anti-TB properties, <i>in silico</i> target validation, molecular docking and dynamics studies of substituted 1,2,4-oxadiazole analogues against <i>Mycobacterium tuberculosis</i>
  作者：Pran Kishore Deb、Nizar A. Al-Shar’i、Katharigatta N. Venugopala、Melendhran Pillay、Pobitra Borah

  DOI：10.1080/14756366.2021.1900162

  日期：2021.1.1

  (3a–3i) and identify their putative drug target, molecular docking and dynamics studies were employed against a panel of 20 mycobacterial enzymes reported to be essential for mycobacterial growth and survival. These computational studies revealed polyketide synthase (Pks13) enzyme as the putative target. Moreover, in silico ADMET predictions showed satisfactory properties for these compounds, collectively

   抽象的 结核分枝杆菌(MTB) 多重耐药和广泛耐药（MDR 和 XDR）菌株的惊人增加促使科学界寻找新颖、有效和更安全的治疗方法。为此，我们对一系列 3,5-二取代-1,2,4-恶二唑衍生物 ( 3a-3i ) 进行了针对 MTB H37Rv、MDR 和 XDR 菌株的测试。其中，对三氟苯基取代的恶二唑化合物3a对易感H37Rv和MDR-MTB菌株表现出优异的活性，MIC值分别为8和16 µg/ml。 为了了解这些化合物 ( 3a–3i ) 的作用机制并确定其假定的药物靶点，我们针对据报道对分枝杆菌生长和存活至关重要的 20 种分枝杆菌酶进行了分子对接和动力学研究。这些计算研究表明聚酮合酶 (Pks13) 是假定的靶标。此外，计算机ADMET 预测显示了这些化合物总体上令人满意的特性，使它们（特别是化合物3a ）成为值得进一步优化的有前景的先导化合物。
• Design, Microwave Assisted Synthesis and Characterization of Substituted 1,2,4-Oxadiazole Analogues as Promising Pharmacological Agents
  作者：Katharigatta N. Venugopala

  DOI：10.14233/ajchem.2017.20626

  日期：——

  various pharmacological activities such as antitussive, anaesthetic [1], anthelmintic [2], anti-HIV [3], antiallergic [4], anticancer [5], anticonvulsant [6], anti-inflammatory [7], antimicrobial [8], antiplatelet, antithrombotic [9], insecticidal [10], monoamine oxidase inhibition [11], muscarinic receptor agonists [12] and selective H3 receptor antagonists [13] properties. Encouraged by these observations

  恶二唑分子支架具有多种药理活性，例如镇咳、麻醉 [1]、驱虫 [2]、抗 HIV [3]、抗过敏 [4]、抗癌 [5]、抗惊厥 [6]、抗炎 [...] 7]、抗菌[8]、抗血小板、抗血栓形成[9]、杀虫[10]、单胺氧化酶抑制[11]、毒蕈碱受体激动剂[12]和选择性H3受体拮抗剂[13]等特性。受到这些观察结果的鼓舞，并继续我们关于合成具有药理特性的新型杂环化合物 [14-17] 和筛选杂环化合物 [18-20] 的多晶型特性的研究工作，我们决定将二苯甲酮部分加入到1,2,4-恶二唑核（Scheme-I）在微波方法的支持下研究产率和总反应时间。
• NITROGEN-CONTAINING AROMATIC HETEROCYCLYL COMPOUND
  申请人：Suzuki Keiko

  公开号：US20120108639A1

  公开（公告）日：2012-05-03

  The present invention provides a compound having excellent regulating action on blood lipid level that is represented by the following general formula (I) or a pharmacologically acceptable salt thereof, wherein, in one embodiment, A represents a 5-membered nitrogen-containing aromatic heterocyclyl group; R 1 represents COOH; each R 2 represents an alkyl; each R 3 represents an optionally substituted phenyl, an optionally substituted phenylalkyl; m represents 0, 1, 2, or 3; n represents 0 or 1; each of R 4 , R 5 , R 6 , and R 7 represents H, an alkyl; and B represents an optionally substituted naphthyl, an optionally substituted aromatic heterocyclyl, or a group represented by the following formula (II) wherein each of B 1 and B 2 represents an optionally substituted phenyl or an optionally substituted aromatic heterocyclyl.

  本发明提供了一种具有优异的调节血脂水平作用的化合物，其表示为以下通式(I)或其药学上可接受的盐，其中，在一种实施例中，A代表5-成员含氮芳香杂环基；R1代表COOH；每个R2代表烷基；每个R3代表可选取代的苯基，可选取代的苯基烷基；m代表0、1、2或3；n代表0或1；每个R4、R5、R6和R7代表H，烷基；B代表可选取代的萘基，可选取代的芳香杂环基，或由以下公式(II)表示的基团，其中，每个B1和B2代表可选取代的苯基或可选取代的芳香杂环基。
• Design, synthesis, characterization, and antibacterial activity of {5-chloro-2-[(3-substitutedphenyl-1,2,4-oxadiazol-5-yl)-methoxy]-phenyl}-(phenyl)-methanones
  作者：Neithnadka Premsai Rai、Venugopala Katharigatta Narayanaswamy、Thavendran Govender、B.K. Manuprasad、Sheena Shashikanth、Pirama Nayagam Arunachalam

  DOI：10.1016/j.ejmech.2010.02.021

  日期：2010.6

  In the present investigation, a series of novel 5-chloro-2-[(3-(substitutedphenyl)-1,2,4-oxadiazol-5-yl)-methoxy]-phenyl}-(phenyl)-methanones (3a-i) have been synthesized from 5-(chloromethyl)-3-sub-stitutedphenyl-1,2,4-oxadiazole (2a-i). The newly synthesized compounds were characterized by IR. NMR (H-1 and C-13), mass spectral and elemental analysis. The title compounds were investigated for in-vitro qualitative (zone of inhibition) and quantitative (MIC) antibacterial activity by agar cup plate and microtitration methods, respectively. The minimum inhibitory concentration and structure activity relationships (SARs) were evaluated. Amongst the synthesized compounds in this series, 5-chloro-2-[(3-(2,5-difluoro-4-methyl-phenyl)-1,2,4-oxadiazol-5-yl)-methoxy]-phenyl}-(phenyl)-methanone (3d) was found to exhibit significant activity with MICs of 21.5, 224, 298 and 306 mu g/mL against Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Klebsiella pneumoniae, respectively.
• 1,2,4-Oxadiazoles--IV. Synthesis and Pharmacological Properties of a Series of Substituted Aminoalkyl-1,2,4-oxadiazoles
  作者：G. Palazzo、M. Tavella、G. Strani、B. Silvestrini

  DOI：10.1021/jm50018a009

  日期：1961.9