5-(4-cyanophenyl)-1,3,4-oxadiazol-2(3H)-one | 128772-82-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(4-cyanophenyl)-1,3,4-oxadiazol-2(3H)-one
• 英文别名: 4-(5-Hydroxy-1,3,4-oxadiazol-2-yl)benzonitrile；4-(2-oxo-3H-1,3,4-oxadiazol-5-yl)benzonitrile
• CAS: 128772-82-7
• 化学式: C₉H₅N₃O₂
• 分子量: 187.158
• InChiKey: PAPSULCRMMWHDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N′-[chloro-(4-cyanophenyl)methylene]-tert-butylcarbazate 在 basic alumina 作用下， 以 氯仿 为溶剂， 反应 0.25h， 以85%的产率得到5-(4-cyanophenyl)-1,3,4-oxadiazol-2(3H)-one
  参考文献：
  名称：

  Synthesis of 5-aryl-3H-[1,3,4]oxadiazol-2-ones from N′-(chloro-aryl-methylene)-tert-butylcarbazates using basic alumina as an efficient and recyclable surface under solvent-free condition

  摘要：

  The synthesis of biologically important 5-aryl-3H-[1,3,4]oxadiazol-2-ones has been carried out by heating the easily synthesized N'-(chloro-aryl-methylene)-tert-butylcarbazates on basic alumina surface under solvent-free condition. The dual characteristic of basic alumina as a solid support as well as a nucleophile is successfully exploited in these reactions. The method provides special attributions such as reduced reaction times, easier work-up procedures, and good to excellent yields as well as increased purity of products and most importantly environmentally friendly protocols. The basic alumina is easily recovered and utilized for further reactions several times without serious loss of activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.128

文献信息

• [EN] COMBINATION PHARMACEUTICAL AGENTS AS RSV INHIBITORS<br/>[FR] AGENTS PHARMACEUTIQUES EN COMBINAISON EN TANT QU'INHIBITEURS DE RSV
  申请人：ENANTA PHARM INC

  公开号：WO2019067864A1

  公开（公告）日：2019-04-04

  The present invention relates to pharmaceutical agents administered to a subject either in combination or in series for the treatment of a Respiratory Syncytial Virus (RSV) infection, wherein treatment comprises administering a compound effective to inhibit the function of the RSV and an additional compound or combinations of compounds having anti-RSV activity.

  本发明涉及用于治疗呼吸道合胞病毒（RSV）感染的药物剂，该药物剂可以单独或连续给予受试者，治疗包括给予一种有效抑制RSV功能的化合物以及具有抗RSV活性的另一种化合物或化合物组合。
• [EN] BENZODIAZEPINE DERIVATIVES AS RSV INHIBITORS<br/>[FR] DÉRIVÉS BENZODIAZÉPINE UTILISÉS COMME INHIBITEURS DU VIRUS RESPIRATOIRE SYNCYTIAL (RSV)
  申请人：ENANTA PHARM INC

  公开号：WO2017015449A1

  公开（公告）日：2017-01-26

  The present invention discloses compounds of Formula (I), or pharmaceutically acceptable salts, esters, or prodrugs thereof: which inhibit Respiratory Syncytial Virus (RSV). The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from RSV infection. The invention also relates to methods of treating an RSV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention.

  本发明公开了化合物的结构式（I），或其药学上可接受的盐、酯或前药：这些化合物抑制呼吸道合胞病毒（RSV）。本发明还涉及包含上述化合物的药物组合物，用于治疗患有RSV感染的受试者。该发明还涉及通过给予包含本发明化合物的药物组合物来治疗受试者的RSV感染的方法。
• Benzodiazepine derivatives as RSV inhibitors
  申请人：Enanta Pharmaceuticals, Inc.

  公开号：US10570153B2

  公开（公告）日：2020-02-25

  The present invention discloses compounds of Formula (I), or pharmaceutically acceptable salts, esters, or prodrugs thereof: which inhibit Respiratory Syncytial Virus (RSV). The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from RSV infection. The invention also relates to methods of treating an RSV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention.

  本发明公开了式（I）化合物或其药学上可接受的盐、酯或原药： 其可抑制呼吸道合胞病毒（RSV）。本发明进一步涉及包含上述化合物的药物组合物，用于给受 RSV 感染的患者用药。本发明还涉及通过施用包含本发明化合物的药物组合物治疗受试者 RSV 感染的方法。
• Combination pharmaceutical agents as RSV inhibitors
  申请人：Enanta Pharmaceuticals, Inc.

  公开号：US10881666B2

  公开（公告）日：2021-01-05

  The present invention relates to pharmaceutical agents administered to a subject either in combination or in series for the treatment of a Respiratory Syncytial Virus (RSV) infection, wherein treatment comprises administering a compound effective to inhibit the function of the RSV and an additional compound or combinations of compounds having anti-RSV activity.

  本发明涉及向受试者联合或系列施用治疗呼吸道合胞病毒（RSV）感染的药剂，其中治疗包括施用一种有效抑制 RSV 功能的化合物和另外一种或多种具有抗 RSV 活性的化合物组合。
• 5-Phenyl-1,3,4-oxadiazol-2(3<i>H</i>)-ones Are Potent Inhibitors of Notum Carboxylesterase Activity Identified by the Optimization of a Crystallographic Fragment Screening Hit
  作者：William Mahy、Nicky J. Willis、Yuguang Zhao、Hannah L. Woodward、Fredrik Svensson、James Sipthorp、Luca Vecchia、Reinis R. Ruza、James Hillier、Svend Kjær、Sarah Frew、Amy Monaghan、Magda Bictash、Patricia C. Salinas、Paul Whiting、Jean-Paul Vincent、E. Yvonne Jones、Paul V. Fish

  DOI：10.1021/acs.jmedchem.0c01391

  日期：2020.11.12

  Carboxylesterase Notum is a negative regulator of the Wnt signaling pathway. There is an emerging understanding of the role Notum plays in disease, supporting the need to discover new small-molecule inhibitors. A crystallographic X-ray fragment screen was performed, which identified fragment hit 1,2,3-triazole 7 as an attractive starting point for a structure-based drug design hit-to-lead program. Optimization of 7 identified oxadiazol-2-one 23dd as a preferred example with properties consistent with druglike chemical space. Screening 23dd in a cell-based TCF/LEF reporter gene assay restored the activation of Wnt signaling in the presence of Notum. Mouse pharmacokinetic studies with oral administration of 23dd demonstrated good plasma exposure and partial blood-brain barrier penetration. Significant progress was made in developing fragment hit 7 into lead 23dd (>600-fold increase in activity), making it suitable as a new chemical tool for exploring the role of Notum-mediated regulation of Wnt signaling.