3-bromo-5-fluoro-4-hydroxybenzonitrile | 1235841-38-9

• 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: 3-bromo-5-fluoro-4-hydroxybenzonitrile
• CAS: 1235841-38-9
• 化学式: C₇H₃BrFNO
• 分子量: 216.009
• InChiKey: NFKJFNKASNIOKU-UHFFFAOYSA-N

物化性质

• 沸点：
  245.0±40.0 °C(Predicted)
• 密度：
  1.87±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-bromo-5-fluoro-4-hydroxybenzonitrile 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 9.0h， 生成 3-fluoro-4-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile
  参考文献：
  名称：

  Potent and Orally Bioavailable Inverse Agonists of RORγt Resulting from Structure-Based Design

  摘要：

  Retinoic acid receptor related orphan receptor gamma t (ROR gamma t), has been identified as the master regulator of T(H)17-cell function and development, making it an attractive target for the treatment of autoimmune diseases by a small-molecule approach. Herein, we describe our investigations on a series of 4-aryl-thienyl acetamides, which were guided by insights from X-ray cocrystal structures. Efforts in targeting the cofactor-recruitment site from the 4-aryl group on the thiophene led to a series of potent binders with nanomolar activity in a primary human-T(H)17-cell assay. The observation of a DMSO molecule binding in a subpocket outside the LBD inspired the introduction of an acetamide into the benzylic position of these compounds. Hereby, a hydrogen-bond interaction of the introduced acetamide oxygen with the backbone amide of Glu379 was established. This greatly enhanced the cellular activity of previously weakly cell-active compounds. The best compounds combined potent inhibition of IL-17 release with favorable PK in rodents, with compound 32 representing a promising starting point for future investigations.

  DOI：

  10.1021/acs.jmedchem.8b00783
• 作为产物：
  描述：

  3-氟-4-羟基苯腈 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 以95.2 %的产率得到3-bromo-5-fluoro-4-hydroxybenzonitrile
  参考文献：
  名称：

  [EN] INHIBITOR OF INTERACTION BETWEEN YAP/TAZ AND TEAD, PREPARATION THEREOF, PHARMACEUTICAL COMPOSITION THEREOF AND USE THEREOF
  [FR] INHIBITEUR DE L'INTERACTION ENTRE YAP/TAZ ET TEAD, SA PRÉPARATION, COMPOSITION PHARMACEUTIQUE ASSOCIÉE ET SON UTILISATION
  [ZH] YAP/TAZ与TEAD相互作用的抑制剂、其制备、药物组合物及应用

  摘要：

  本公开提供下式I所示的YAP/TAZ与TEAD相互作用的抑制剂、其制备、药物组合物及应用。本公开提供的化合物可作为YAP/TAZ与TEAD相互作用的抑制剂，用于治疗或预防YAP/TAZ与TEAD相互作用介导的疾病。

  公开号：

  WO2023155927A1

文献信息

• [EN] NOVEL COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS THEREOF FOR THE TREATMENT OF INFLAMMATORY DISORDERS<br/>[FR] NOUVEAUX COMPOSÉS ET COMPOSITIONS PHARMACEUTIQUES LES COMPRENANT POUR LE TRAITEMENT DE TROUBLES INFLAMMATOIRES
  申请人：GALAPAGOS NV

  公开号：WO2017012647A1

  公开（公告）日：2017-01-26

  The present invention discloses compounds according to Formula (I), wherein R1, R3, R4, R5, L1, and Cy are as defined herein. The present invention also provides compounds, methods for the production of said compounds of the invention, pharmaceutical compositions comprising the same and their use in allergic or inflammatory conditions, autoimmune diseases, proliferative diseases, transplantation rejection, diseases involving impairment of cartilage turnover, congenital cartilage malformations, and/or diseases associated with hypersecretion of IL6 and/or interferons. The present invention also methods for the prevention and/or treatment of the aforementioned diseases by administering a compound of the invention.

  本发明公开了根据式（I）的化合物，其中R1、R3、R4、R5、L1和Cy如本文所定义。本发明还提供了该发明的化合物、制备该化合物的方法、包括相同化合物的药物组合物以及它们在过敏或炎症症状、自身免疫疾病、增殖性疾病、移植排斥、涉及软骨周转障碍的疾病、先天软骨畸形和/或与IL6和/或干扰素过度分泌相关的疾病中的使用。本发明还提供了通过给予该发明的化合物来预防和/或治疗上述疾病的方法。
• Preparation of fluorophenols, fluorohalophenols, N-acylfluoroanilines, and N-acylfluorohaloanilines
  申请人：DOWELANCO

  公开号：EP0470669A2

  公开（公告）日：1992-02-12

  Chloro and bromophenols and N-acylanilines are fluorinated in an ortho or para position with an N-fluoropyridinium salt to obtain fluorohalophenols and N-acylfluorohaloanilines, which can be further converted to fluorophenols and N-acylfluoroanilines by reduction. Thus, o-fluorophenol is obtained by fluorination of p-bromophenol with 2-chloro-6-(trichloromethyl)pyridinium fluoroborate and reduction of the product obtained with sodium formate and a palladium catalyst. N-Fluoropyridinium salts having trichloromethyl substituents are disclosed.

  氯代和溴代苯酚及 N-酰基苯胺与 N-氟吡啶鎓盐进行正位或对位氟化反应，可得到氟卤苯酚和 N-酰基氟卤苯胺，再通过还原反应将其转化为氟苯酚和 N-酰基氟苯胺。因此，邻氟苯酚是通过对溴苯酚与 2-氯-6-(三氯甲基)吡啶鎓氟硼酸盐氟化，然后用甲酸钠和钯催化剂还原所得到的产物而得到的。本发明公开了具有三氯甲基取代基的 N-氟吡啶鎓盐。
• [EN] SYNERGISTIC FUNGICIDAL COMPOSITIONS INCLUDING HYDRAZONE DERIVATIVES AND COPPER<br/>[FR] COMPOSITIONS FONGICIDES SYNERGIQUES À BASE DE DÉRIVÉS D'HYDRAZONE ET DE CUIVRE
  申请人：DOW AGROSCIENCES LLC

  公开号：WO2010083307A3

  公开（公告）日：2010-10-28
• US5116982A
  申请人：——

  公开号：US5116982A

  公开（公告）日：1992-05-26
• US5164502A
  申请人：——

  公开号：US5164502A

  公开（公告）日：1992-11-17