3-fluoro-4'-trifluoromethyl-biphenyl-4-carbaldehyde | 871250-25-8

• 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-fluoro-4'-trifluoromethyl-biphenyl-4-carbaldehyde
• 英文别名: 2-fluoro-4-(4-trifluoromethylphenyl)benzaldehyde；3-Fluoro-4'-(trifluoromethyl)biphenyl-4-carbaldehyde；2-fluoro-4-[4-(trifluoromethyl)phenyl]benzaldehyde
• CAS: 871250-25-8
• 化学式: C₁₄H₈F₄O
• 分子量: 268.211
• InChiKey: VJXJYGCBKLXIPV-UHFFFAOYSA-N

物化性质

• 沸点：
  320.0±42.0 °C(Predicted)
• 密度：
  1.314±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-fluoro-4'-trifluoromethyl-biphenyl-4-carbaldehyde 在 硫酸羟胺 、 1,3-二甲基咪唑 碘 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 1.5h， 生成 4-((4-((3-fluoro-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)(hydroxylimino)methyl)pyrimidin-2-yl)amino)benzonitrile
  参考文献：
  名称：

  Privileged scaffold inspired design of novel oxime-biphenyl-DAPYs in treatment of HIV-1

  摘要：

  Oxime is a key pharmacophore in drug development. The biphenyl diarylpyrimidines (DAPYs) have been developed by our group as novel non-nucleoside reverse transcriptase inhibitors (NNRTIs). In this study, fourteen oxime-biphenyl-DAPYs were designed and synthesized through a privileged scaffold inspired design strategy. They exhibited promising activity toward wild type HIV-1 and single mutant strains. Compound 7d was found to be the most potent one against both wild type (EC50 = 12.1 nM) and E138K mutant strains (EC50 = 0.0270 mu M). It also had a much lower cytotoxicity (CC50 > 292 mu M) and higher selective index (SI > 24105) than those of the FDA-approved drugs efavirenz and etravirine. Molecular docking and dynamics simulation predicted and disclosed the binding mode of compound 7d with the RT, providing the explanation on the antiviral activity. These results were helpful for subsequent structural optimizations in anti-HIV-1 drug discovery.

  DOI：

  10.1016/j.bioorg.2020.103825
• 作为产物：
  描述：

  4-三氟甲基苯硼酸 、 4-溴-2-氟苯甲醛 在 palladium diacetate 四丁基溴化铵 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 以86%的产率得到3-fluoro-4'-trifluoromethyl-biphenyl-4-carbaldehyde
  参考文献：
  名称：

  [EN] GLUCAGON RECEPTOR ANTAGONISTS, PREPARATION AND THERAPEUTIC USES
  [FR] ANTAGONISTES VIS-A-VIS DES RECEPTEURS DU GLUCAGON, ELABORATION ET UTILISATIONS THERAPEUTIQUES

  摘要：

  本发明揭示了式(I)的新化合物，或其药用可接受的盐，具有胰高血糖素受体拮抗剂或逆拮抗剂活性，以及制备这类化合物的方法。在另一实施方式中，本发明揭示了包括式(I)化合物的药物组合物，以及使用它们治疗糖尿病和其他胰高血糖素相关代谢紊乱等方法。

  公开号：

  WO2005118542A1

文献信息

• Glucagon Receptor Antagonists, Preparation and Therapeutic Uses
  申请人：Chappell Mark Donald

  公开号：US20080125468A1

  公开（公告）日：2008-05-29

  The present invention discloses novel compounds of Formula (I), or pharmaceutically acceptable salts thereof, which have glucagon receptor antagonist or inverse agonist activity, as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising compounds of Formula (I) as well as methods of using them to treat diabetic and other glucagon related metabolic disorders, and the like.

  本发明揭示了式（I）的新化合物或其药学上可接受的盐，其具有胰高血糖素受体拮抗剂或反向激动剂活性，以及制备这种化合物的方法。在另一种实施方式中，本发明揭示了包含式（I）化合物的药物组合物，以及使用它们治疗糖尿病和其他与胰高血糖素相关的代谢性疾病的方法。
• Glucagon receptor antagonists, preparation and therapeutic uses
  申请人：Eli Lilly and Company

  公开号：US07989457B2

  公开（公告）日：2011-08-02

  The present invention discloses novel compounds of Formula (I), or pharmaceutically acceptable salts thereof, which have glucagon receptor antagonist or inverse agonist activity, as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising compounds of Formula (I) as well as methods of using them to treat diabetic and other glucagon related metabolic disorders, and the like.

  本发明披露了一种新的化合物I式，或其药学上可接受的盐，具有胰高血糖素受体拮抗剂或反向激动剂活性，以及制备这种化合物的方法。在另一种实施方式中，本发明披露了包含I式化合物的药物组合物，以及使用它们治疗糖尿病和其他胰高血糖素相关代谢紊乱等疾病的方法。
• Pyrimidinone compounds
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP1479671B1

  公开（公告）日：2009-05-27
• GLUCAGON RECEPTOR ANTAGONISTS, PREPARATION AND THERAPEUTIC USES
  申请人：ELI LILLY AND COMPANY

  公开号：EP1758859B1

  公开（公告）日：2013-07-17
• PESTICIDALLY ACTIVE POLYCYCLIC DERIVATIVES WITH SULFUR CONTAINING SUBSTITUENTS
  申请人：Syngenta Participations AG

  公开号：EP3214939B1

  公开（公告）日：2020-02-19