4-(4-methoxyphenyl)-5-phenylisoxazole | 116485-59-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-methoxyphenyl)-5-phenylisoxazole
• 英文别名: 4-(4-Methoxyphenyl)-5-phenyl-1,2-oxazole
• CAS: 116485-59-7
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: PRTMKQUBPHTFFL-UHFFFAOYSA-N

物化性质

• 熔点：
  69-70 °C(Solv: hexane (110-54-3); benzene (71-43-2))
• 沸点：
  388.5±37.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(4-methoxyphenyl)-1-phenyl-2,3-ditosyloxypropanone 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 为溶剂， 以78%的产率得到4-(4-methoxyphenyl)-5-phenylisoxazole
  参考文献：
  名称：

  The Chemistry of α,β-Ditosyloxy Ketones: A New and Convenient Route to 4,5-Diarylisoxazoles from α,β-Chalcone Ditosylates

  摘要：

  α,β-香豆素二托烯与盐酸羟胺在适当条件下反应，会发生1,2-芳基迁移，从而提供了一条合成4,5-二取代异噻唑的新路径。

  DOI：

  10.1055/s-0031-1290109

文献信息

• Computational modeling and target synthesis of monomethoxy-substituted o-diphenylisoxazoles with unexpectedly high antimitotic microtubule destabilizing activity
  作者：Victor S. Stroylov、Igor V. Svitanko、Anna S. Maksimenko、Victor P. Kislyi、Marina N. Semenova、Victor V. Semenov

  DOI：10.1016/j.bmcl.2020.127608

  日期：2020.12

  predicted using computational modeling, docking studies, and calculation of binding affinity. The respective molecules were synthesized in high yields by three steps reaction using easily available benzaldehydes, acetophenones, and arylnitromethanes as starting material. The calculated antitubulin effect was confirmed in vivo in a sea urchin embryo model. Compounds 2a and 2c showed high antimitotic microtubule

  使用计算模型，对接研究和结合亲和力的计算预测了单甲氧基取代的邻-二苯基异恶唑2a-d与微管蛋白的秋水仙碱位点相互作用的能力。使用容易获得的苯甲醛，苯乙酮和芳基硝基甲烷作为起始原料，通过三步反应以高收率合成各个分子。在海胆胚胎模型中体内证实了所计算的抗微管蛋白作用。化合物2a和2c与CA4相比，具有较高的抗有丝分裂微管去稳定活性。在NCI60筛选中，异恶唑2a还显示出对人癌细胞的明显细胞毒性。首次将仅具有一个甲氧基取代基的异恶唑连接的CA4衍生物2a和2c鉴定为有效的抗有丝分裂微管去稳定剂。这些分子可以被认为是有希望进一步优化的结构。
• Use of small molecule compounds for immunopotentiation
  申请人：Valiante M. Nicholas

  公开号：US20050136065A1

  公开（公告）日：2005-06-23

  The invention provides immunostimulatory compositions comprising a small molecule immuno-poteniator (SMIP) compound and methods of administration thereof. Also provided are methods of administering a SMIP compound in an effective amount to enhance the immune response of a subject to an antigen. Further provided are novel compositions and methods of administering SMIP compounds alone or in combination with another agent for the treatment of cancer, infectious diseases and/or allergies/asthma.

  本发明提供了包含小分子免疫增强剂（SMIP）化合物的免疫刺激组合物及其给药方法。还提供了在有效剂量下给予SMIP化合物以增强受体对抗原的免疫反应的方法。此外，还提供了用于治疗癌症、传染性疾病和/或过敏/哮喘的新型组合物和给药SMIP化合物的方法，单独或与另一种药物联合使用。
• Severe acute respiratory syndrome coronavirus
  申请人：Rappuoli Rino

  公开号：US20060257852A1

  公开（公告）日：2006-11-16

  An outbreak of a virulent respiratory virus, now known as Severe Acute Respiratory Syndrome (SARS), was identified in Hong Kong, China and a growing number of countries around the world in 2003. The invention relates to nucleic acids and proteins from the SARS coronavirus. These nucleic acids and proteins can be used in the preparation and manufacture of vaccine formulations, diagnostic reagents, kits, etc. The invention also provides methods for treating SARS by administering small molecule antiviral compounds, as well as methods of identifying potent small molecules for the treatment of SARS.

  2003年，在中国香港和世界各地越来越多的国家中，爆发了一种名为严重急性呼吸综合症（SARS）的致命呼吸道病毒。本发明涉及来自SARS冠状病毒的核酸和蛋白质。这些核酸和蛋白质可以用于制备和制造疫苗配方、诊断试剂盒等。本发明还提供了通过给予小分子抗病毒化合物治疗SARS的方法，以及识别用于治疗SARS的有效小分子的方法。
• Use of organic compounds for immunopotentiation
  申请人：Novartis Vaccines and Diagnostics, Inc.

  公开号：EP2258365A1

  公开（公告）日：2010-12-08

  The invention provides immunostimulatory compositions comprising a small molecule immuno-poteniator (SMIP) compound and methods of administration thereof. Also provided are methods of administering a SMIP compound in an effective amount to enhance the immune response of a subject to an antigen. Further provided are novel compositions and methods of administering SMIP compounds alone or in combination with another agent for the treatment of cancer, infectious diseases and/or allergies/asthma.

  本发明提供了包含小分子免疫增强剂（SMIP）化合物的免疫刺激组合物及其施用方法。还提供了施用有效量的 SMIP 化合物以增强受试者对抗原的免疫应答的方法。此外，还提供了单独施用 SMIP 化合物或与另一种制剂联合施用 SMIP 化合物以治疗癌症、传染性疾病和/或过敏/哮喘的新型组合物和方法。
• Small molecule immunopotentiators and assays for their detection
  申请人：Novartis Vaccines and Diagnostics, Inc.

  公开号：EP2583678A2

  公开（公告）日：2013-04-24

  The invention provides immunostimulatory compositions comprising a small molecule immuno-potentiator (SMIP) compound and methods of administration thereof. Also provided are methods of administering a SMIP compound in an effective amount to enhance the immune response of a subject to an antigen. Further provided are novel compositions and methods of administering SMIP compounds alone or in combination with another agent for the treatment of cancer, infectious diseases and/or allergies/asthma. In a further aspect, the invention relates generally to methods of screening for small molecule immuno-modulatory compositions.

  本发明提供了包含小分子免疫促进剂（SMIP）化合物的免疫刺激组合物及其施用方法。还提供了施用有效量的 SMIP 化合物以增强受试者对抗原的免疫应答的方法。本发明还提供了单独施用 SMIP 化合物或与另一种制剂联合施用 SMIP 化合物以治疗癌症、传染性疾病和/或过敏/哮喘的新型组合物和方法。在另一方面，本发明一般涉及筛选小分子免疫调节组合物的方法。