3-(5-phenylisoxazol-3-yl)pyridine | 85903-26-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(5-phenylisoxazol-3-yl)pyridine
• 英文别名: 3-(3-pyridyl)-5-phenylisoxazole；5-phenyl-3-(3-pyridyl)isoxazole；3-(5-phenyl-isoxazol-3-yl)-pyridine；3-(3'-pyridinyl)-5-phenylisoxazole；5-phenyl-3-(pyridin-3-yl)isoxazole；5-Phenyl-3-β-pyridyl-isoxazol；5-phenyl-3-pyridin-3-yl-1,2-oxazole
• CAS: 85903-26-0
• 化学式: C₁₄H₁₀N₂O
• 分子量: 222.246
• InChiKey: ADEVNZXMBGDRQL-UHFFFAOYSA-N

物化性质

• 熔点：
  143-144 °C(Solv: ligroine (8032-32-4))
• 沸点：
  420.5±30.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-吡啶醛肟 在 氯 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 3-(5-phenylisoxazol-3-yl)pyridine
  参考文献：
  名称：

  5-Substituted pyridylisoxazoles as effective inhibitors of platelet aggregation

  摘要：

  一系列5位取代的3-吡啶基异恶唑被合成，通过使用氰氧基与炔烃的[3+2]环加成反应变化异恶唑环的5位取代基，无需额外的合成阶段，并保留了异恶唑环3位的2-吡啶基、3-吡啶基和4-吡啶基取代基。取代的吡啶基异恶唑是一类潜在的抗聚集药物，体外活性浓度范围为1•10−6 mol L−1至1•10−4 mol L−1，对以花生四烯酸作为聚集诱导剂的人富血小板血浆有效。这些化合物不作为环氧合酶或血栓素合成酶的抑制剂，也不是凝血酶的抑制剂。

  DOI：

  10.1007/s11172-014-0707-3

文献信息

• Novel Isoxazoles and Methods of Use Thereof
  申请人：Gopalakrishnan Murali

  公开号：US20090306096A1

  公开（公告）日：2009-12-10

  The invention relates to isoxazole derivatives, compositions comprising such compounds, and methods of preventing or treating conditions and disorders using such compounds and compositions.

  这项发明涉及异唑烷衍生物，包括这些化合物的组合物，以及使用这些化合物和组合物预防或治疗疾病和疾病的方法。
• Cyclocondensation of Hydroxylamine with 1,3-Bis(het)arylmonothio 1,3-Diketones and 1,3-Bis(het)aryl-3-(methylthio)-2-prop­enones: Synthesis of 3,5-Bis(het)arylisoxazoles with Complementary Regioselectivity
  作者：Byregowda Raghava、Gangajji Parameshwarappa、Anand Acharya、Toreshettahally R. Swaroop、Kanchugarakoppal S. Rangappa、Hiriyakkanavar Ila

  DOI：10.1002/ejoc.201301667

  日期：2014.3

  monothio-substituted 1,3-diketones is installed at the 3-position. On the other hand, the reaction of hydroxylamine hydrochloride with 3-(methylthio)-1,3-bis(het)aryl-2-propenones 2 in the presence of barium hydroxide in refluxing ethanol gave 3,5-bis(het)arylisoxazoles 6 with complementary regioselectivity in high yields. A probable mechanism for the formation of regioisomeric isoxazoles 5 and 6 from precursors

  已经开发了区域选择性合成具有互补区域选择性的 3,5-双（杂）芳基异恶唑的有效途径。该方法包括盐酸羟胺与 1,3-双（杂）芳基-单硫代取代的 1,3-二酮 1 或与 3-甲硫基-1,3-双（杂）芳基-2-丙烯酮 2 在各种反应条件。在第一个方案中，在醋酸钠/醋酸（pH 2.2）的存在下，在回流的乙醇/苯中用盐酸羟胺处理二酮 1，得到 3,5-双（杂）芳基异恶唑 5，其中杂（芳基）与单硫代取代的 1,3-二酮的硫代羰基相连的部分位于 3-位。另一方面，盐酸羟胺与3-(甲硫基)-1反应，3-双(杂)芳基-2-丙烯酮2在氢氧化钡存在下在回流乙醇中以高产率得到具有互补区域选择性的3,5-双(杂)芳基异恶唑6。已经提出了由前体 1 和 2 形成区域异构异恶唑 5 和 6 的可能机制。
• Isoxazoles: synthesis, evaluation and bioinformatic design as acetylcholinesterase inhibitors
  作者：Margarita Gutiérrez、María Francisca Matus、Tomas Poblete、Jessica Amigo、Gabriel Vallejos、Luis Astudillo

  DOI：10.1111/jphp.12180

  日期：2013.11.18

  Inhibition of acetylcholinesterase (AChE) is a common treatment for early stages of Alzheimer's disease. In this study, nine isoxazoles derivatives were tested for their in-vitro AChE activity. The molecular docking showed the interaction of the compounds with the active site.

  The isoxazoles were synthesized using 1,3-dipolar cycloaddition in the presence of sodium hypochlorite. They were also isolated and characterized by spectroscopic methods. The in-vitro activity was measured by an adapted version of Ellman's assay.

  The isoxazoles are described as inhibitors of AChE. The most potent compound in the series exhibited a moderate inhibitory activity (50% inhibitory concentration = 134.87 μm). The design of new compounds was created by using the RACHEL module of the SYBYL software.

  Our research provided enough evidence of the efficacy of isoxazoles as AChE inhibitors. The isoxazoles were synthesized and evaluated as inhibitors of AChE. The docking study based on a novel series of complexes isoxazole with AChE from Electroporus electricus has demonstrated that the ligand bind is similar to the compounds used as reference. To find new candidates with the isoxazole core that act as inhibitors of AChE, part of the structure of the compound 9 was used for de-novo design. Molecular docking models of the ligand-AChE complexes suggest that the compound 10 is located on the periphery of the AChE active site.

  抑制乙酰胆碱酯酶（AChE）是早期阿尔茨海默病的常见治疗方法。本研究测试了九种异噁唑衍生物的体外AChE活性。分子对接显示化合物与活性位点的相互作用。

  使用次氯酸钠存在下进行1,3-偶极环加成合成异噁唑。通过光谱方法进行分离和表征。体外活性采用改良版Ellman's测定法测量。

  异噁唑被描述为AChE的抑制剂。该系列中最有效的化合物表现出中等的抑制活性（50％抑制浓度= 134.87μm）。使用SYBYL软件的RACHEL模块设计了新化合物。

  我们的研究提供了足够的证据证明异噁唑作为AChE抑制剂的功效。我们合成和评估了异噁唑作为AChE抑制剂。基于Electroporus electricus中异噁唑与AChE的新系列复合物的对接研究表明，配体结合类似于参考化合物。为了寻找具有异噁唑核心的新候选物作为AChE抑制剂，使用化合物9的一部分结构进行了de-novo设计。配体-AChE复合物的分子对接模型表明，化合物10位于AChE活性位点的周缘。

• Isoxazole based neuronal nicotinic receptor ligands and methods of use
  申请人：Gopalakrishnan Murali

  公开号：US08383658B2

  公开（公告）日：2013-02-26

  The invention relates to isoxazole derivatives, compositions comprising such compounds, and methods of preventing or treating conditions and disorders using such compounds and compositions.

  本发明涉及异唑啉衍生物、包含此类化合物的组合物以及使用此类化合物和组合物预防或治疗疾病和疾病的方法。
• Synthesis, Characterization, DFT Study, Molecular Modelling and Biological Evaluation of Novel 5-Aryl-3-(pyridine-3-yl)isoxazole Hybrids as Potent Anticancer Agents with Inhibitory Effect on Skin Cancer
  作者：S. Subi、S. Viola Rose、T.F. Abbs Fen Reji

  DOI：10.14233/ajchem.2021.23335

  日期：——

  A novel series of pyridinyl isoxazole derivatives was synthesized and characterized by IR, 1H and 13C NMR and high-resolution mass spectrometry. Geometrical and electronic properties of pyridinyl isoxazole derivative was investigated by using B3LYP/6-31G (d,p) basis sets. The HOMO and LUMO analysis was used to determine the charge transfer within the molecule. The pyridinyl isoxazole derivatives exhibited good docking scores against liver cancer 4MMH. The results revealed clearly compound 2b exhibited better radical scavenging ability. Among the synthesized pyridinyl isoxazole derivatives, compound 2b was highly active on the SKMEL cell line (human skin cancer).

  合成了一系列新型吡啶基异噁唑衍生物，并通过红外、1H 和 13C 核磁共振和高分辨质谱法对其进行了表征。对吡啶基异恶唑衍生物的几何和电子特性进行了研究。 使用 B3LYP/6-31G (d,p) 基集研究了吡啶基异恶唑衍生物的几何和电子性质。利用 HOMO 和 LUMO 分析来确定分子内的电荷转移。吡啶基异恶唑 衍生物对肝癌 4MMH 具有良好的对接效果。结果表明 化合物 2b 具有更好的自由基清除能力。在合成的吡啶基异恶唑 在合成的吡啶基异噁唑衍生物中，化合物 2b 对 SKMEL 细胞系（人类皮肤癌）具有很高的活性。