2-(4-chlorophenoxy)-5-nitrobenzonitrile | 78940-65-5

• 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: 2-(4-chlorophenoxy)-5-nitrobenzonitrile
• 英文别名: Benzonitrile, 2-(4-chlorophenoxy)-5-nitro-
• CAS: 78940-65-5
• 化学式: C₁₃H₇ClN₂O₃
• 分子量: 274.663
• InChiKey: LIWRJJIPQLEUEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenoxy)-5-nitrobenzonitrile 在 亚磷酸三苯酯 、 铁粉 、 氯化铵 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 反应 14.0h， 生成 3,5-dichloro-N-(4-(4-chlorophenoxy)-3-cyanophenyl)-2-hydroxybenzamide
  参考文献：
  名称：

  Salicylanilides Reduce SARS-CoV-2 Replication and Suppress Induction of Inflammatory Cytokines in a Rodent Model

  摘要：

  DOI：

  10.1021/acsinfecdis.1c00253
• 作为产物：
  描述：

  2-氯-5-硝基苯甲腈 、 对氯苯酚 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 生成 2-(4-chlorophenoxy)-5-nitrobenzonitrile
  参考文献：
  名称：

  Substituted benzonitriles having antiviral activity

  摘要：

  揭示了具有抗病毒活性的取代苯腈。基于这些化合物的抗病毒活性的使用方法也被揭示，以及包含载体与适当抗病毒活性化合物结合的组合物。

  公开号：

  US04332820A1

文献信息

• Structure-Guided Discovery of Novel, Potent, and Orally Bioavailable Inhibitors of Lipoprotein-Associated Phospholipase A2
  作者：Qiufeng Liu、Fubao Huang、Xiaojing Yuan、Kai Wang、Yi Zou、Jianhua Shen、Yechun Xu

  DOI：10.1021/acs.jmedchem.7b01530

  日期：2017.12.28

  inhibitors derived from a relatively weak fragment. Similarity searching on this fragment followed by molecular docking leads to the discovery of a micromolar inhibitor with a 300-fold potency improvement. Subsequently, by the application of a structure-guided design strategy, a successful hit-to-lead optimization was achieved and a number of Lp-PLA2 inhibitors with single-digit nanomolar potency were obtained

  脂蛋白相关的磷脂酶A2（Lp-PLA2）是动脉粥样硬化，阿尔茨海默氏病和糖尿病性黄斑水肿的有希望的治疗靶标。在这里，我们报告鉴定衍生自相对较弱的片段的新型磺酰胺支架Lp-PLA2抑制剂。在该片段上进行相似搜索，然后进行分子对接，导致发现了一种微摩尔抑制剂，其效价提高了300倍。随后，通过应用结构指导的设计策略，成功实现了从头至尾的优化，并获得了许多具有单位数纳摩尔效价的Lp-PLA2抑制剂。在初步评估了体内和体外的药物相似性后，将化合物37该同类抑制剂系列在雄性Sprague-Dawley大鼠中具有良好的抑制活性和良好的口服生物利用度，从而脱颖而出，为进一步开发提供了良好的候选者。因此，本研究清楚地证明了在有效的铅发现项目中整合使用片段筛选，晶体结构确定，虚拟筛选和药物化学的功能和优势，为基于结构的药物设计提供了一个很好的例子。
• Substituted benzonitriles having antiviral activity
  申请人：The Dow Chemical Company

  公开号：US04332820A1

  公开（公告）日：1982-06-01

  Substituted benzonitriles having antiviral activity are disclosed. Methods of use based on the antiviral activity of the compounds are also disclosed, as well as compositions which comprise a carrier in combination with a suitable antiviral active compound.

  揭示了具有抗病毒活性的取代苯腈。基于这些化合物的抗病毒活性的使用方法也被揭示，以及包含载体与适当抗病毒活性化合物结合的组合物。
• Substituted benzonitriles and compositions for inhibiting viruses
  申请人：THE DOW CHEMICAL COMPANY

  公开号：EP0034263A2

  公开（公告）日：1981-08-26

  Substituted benzonitriles of the formula wherein X represents an oxygen or sulfur atom; R'represents bromo, chloro, fluoro, phenoxy, alkylthio, alkylsulfinyl, alkylsulfonyl alkylaminosulfonyl, dialkylaminosulfonyl, benzoyl, alkoxy, alkyl, halogenated alkyl or acetyl; and R2 represents hydrogen, bromo, chloro, fluoro, or trifluoromethyl; and n represents the integer 1, 2, or 4, having antiviral activity are disclosed. Methods of use based on the antiviral activity of the compounds are also disclosed, as well as compositions which comprise a carrier in combination with a suitable antiviral active compound.

  式中的取代苯腈 其中，X 代表氧原子或硫原子；R'代表溴、氯、氟、苯氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基氨基磺酰基、二烷基氨基磺酰基、苯甲酰基、烷氧基、烷基、卤代烷基或乙酰基；以及 R2 代表氢、溴、氯、氟或三氟甲基；n 代表整数 1、2 或 4，这些化合物具有抗病毒活性。还公开了基于化合物抗病毒活性的使用方法，以及包含载体与合适的抗病毒活性化合物的组合物。
• Salicylanilide Analog Minimizes Relapse of <i>Clostridioides difficile</i> Infection in Mice
  作者：Steven Blake、Rajani Thanissery、Alissa J. Rivera、Mark S. Hixon、Mingliang Lin、Casey M. Theriot、Kim D. Janda

  DOI：10.1021/acs.jmedchem.0c00123

  日期：2020.7.9

  Clostridioides difficile infection (CDI) causes serious and sometimes fatal symptoms like diarrhea and pseudomem-branous colitis. Although antibiotics for CDI exist, they are either expensive or cause recurrence of the infection due to their altering the colonic microbiota, which is necessary to suppress the infection. Here, we leverage a class of known membrane-targeting compounds that we previously showed to have broad inhibitory activity across multiple Clostridioides difficile strains while preserving the microbiome to develop an efficacious agent. A new series of salicylanilides was synthesized, and the most potent analog was selected through an in vitro inhibitory assay to evaluate its pharmacokinetic parameters and potency in a CDI mouse model. The results revealed reduced recurrence of CDI and diminished disturbance of the microbiota in mice compared to standard-of-care vancomycin, thus paving the way for novel therapy that can potentially target the cell membrane of C. difficile to minimize relapse in the recovering patient.
• EP0034263B1
  申请人：——

  公开号：EP0034263B1

  公开（公告）日：1984-09-26