6-fluoro-3-methyl-2-(4-phenoxyphenyl)quinoline-4-carboxylic acid | 96187-36-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-fluoro-3-methyl-2-(4-phenoxyphenyl)quinoline-4-carboxylic acid
• 英文别名: 6-fluoro-3-methyl-2-(4-phenoxyphenyl)-4-quinoline-carboxylic acid
• CAS: 96187-36-9
• 化学式: C₂₃H₁₆FNO₃
• 分子量: 373.383
• InChiKey: ODILYAYKQDDXJJ-UHFFFAOYSA-N

物化性质

• 沸点：
  532.7±50.0 °C(Predicted)
• 密度：
  1.307±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-氟靛红 、 4-苯氧基苯丙酮 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 48.0h， 以34%的产率得到6-fluoro-3-methyl-2-(4-phenoxyphenyl)quinoline-4-carboxylic acid
  参考文献：
  名称：

  SAR-Based Optimization of a 4-Quinoline Carboxylic Acid Analogue with Potent Antiviral Activity

  摘要：

  It is established that drugs targeting viral proteins are at risk of generating resistant strains. However, drugs targeting host factors can potentially avoid this problem. Herein, we report structure-ctivity relationship studies leading to the discovery of a very potent lead compound 6-fluoro-2-(5-isopropyl-2-methyl-4-phenoxyphenyl) quinoline -4-carboxylic acid (C44) that inhibits human dihydroorotate dehydrogenase (DHODH) with an IC50 of 1 nM and viral replication of VSV and WSN-Influenza with an EC50 of 2 nM and 41 nM. We also solved the X-ray structure of human DHODH bound to C44, providing structural insight into the potent inhibition of biaryl ether analogues of brequinar.

  DOI：

  10.1021/ml300464h

文献信息

• [EN] TREATMENT OF ORGAN TRANSPLANTATION REJECTION
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：WO1991019498A1

  公开（公告）日：1991-12-26

  (EN) 4-Quinoline-carboxylic acid derivatives, such as 2-(2'-fluoro-1,1'-biphenyl-4-yl)-6-fluoro-3-methyl-4-quinoline carboxylic acid, in combination with other immunosuppressive agents are useful for the treatment and/or prevention of transplantation rejection, graft vs. host disease, autoimmune diseases, and chronic inflammatory disease.(FR) Des dérivés d'acide quinoléine-4-carboxylique, par exemple l'acide 2-(2'-fluoro-1,1'-biphényle-4-yle)-6-fluoro-3-méthyle-4-quinoléine carboxylique, associés à d'autres agents immunosuppresseurs, sont utiles au traitement et/ou à la prévention du rejet du greffon, de la réaction du greffon contre l'hôte, des maladies auto-immunes et des affections inflammatoires chroniques.

  4-喹啉羧酸衍生物，例如2-(2'-氟-1,1'-联苯基-4-基)-6-氟-3-甲基-4-喹啉羧酸，与其他免疫抑制剂联合使用可用于治疗和/或预防移植排斥、移植物抗宿主病、自身免疫性疾病和慢性炎症性疾病。
• Treatment of cancer in mammals by concurrent administration of 4-quinoline carboxylic acid derivatives and interleukin-2
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0362578A1

  公开（公告）日：1990-04-11

  Interleukin-2 (IL-2) in combination with 4-quinoline carboxylic acids and derivatives thereof, such as 2-(2′-fluoro-1,1′-biphenyl-­4-yl)-6-fluoro-3-methyl-4-quinoline carboxylic acid, are useful for the treatment of solid tumors in mammals. The tumor-inhibiting effect of the combination of IL-2 and quinoline carboxylic acids exceeds the effect of either agent alone.

  白细胞介素-2（IL-2）与4-喹啉羧酸及其衍生物（如2-(2'-氟-1,1'-联苯-4-基)-6-氟-3-甲基-4-喹啉羧酸）的组合物，可用于哺乳动物实体瘤的治疗。IL-2和喹啉羧酸的组合物的抑制肿瘤效果超过单独使用任何一种药物的效果。
• Phenylquinolinecarboxylic acids and derivatives as antitumor agents
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0133244A2

  公开（公告）日：1985-02-20

  Phenylquinolinecarboxylic acids and derivatives thereof, such as 2-(2'-fluoro-1,1'-biphenyl-4-yi)-6-fluoro-3-methyl-4-quinolinecarboxylic acid, or a sodium or potassium salt thereof, are useful as tumor inhibiting agents. Related Application This application is a continuation-in-part of my copending application U.S. Serial No. 516,319, filed July 22, 1983.

  苯基喹啉羧酸及其衍生物，如 2-(2'-氟-1,1'-联苯-4-基)-6-氟-3-甲基-4-喹啉羧酸或其钠盐或钾盐，可用作肿瘤抑制剂。相关申请 本申请是 1983 年 7 月 22 日提交的美国系列号 516,319 号共同申请的部分延续。
• 4-Quinoline carboxylic acid derivatives useful as immunosuppressive agents
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：EP0339485A1

  公开（公告）日：1989-11-02

  4-Quinolinecarboxylic acids and derivatives thereof, such as 2-(2′-fluoro-1,1′-biphenyl-4-yl)-­6-fluoro-3-methyl-4-quinolinecarboxylic acid, are useful as immunomodulatory and anti-inflammatory agents. Pharmaceutical formulations containing such compounds are useful for the treatment of autoimmune diseases, transplantation rejection, graft vs. host disease, and chronic inflammatory disease such as rheumatoid arthritis.

  4-喹啉羧酸及其衍生物，如 2-(2′-氟-1,1′-联苯-4-基)-6-氟-3-甲基-4-喹啉羧酸，可用作免疫调节剂和抗炎剂。含有此类化合物的药物制剂可用于治疗自身免疫性疾病、移植排斥反应、移植物抗宿主疾病和慢性炎症性疾病，如类风湿性关节炎。
• 4-Quinoline carboxylic acid derivatives useful for treating skin and muco-epithelial diseases
  申请人：THE DU PONT MERCK PHARMACEUTICAL COMPANY

  公开号：EP0339484B1

  公开（公告）日：1993-01-20