3-amino-4'-fluoro-(1,1'-biphenyl)-4-carbonitrile | 1197199-76-0

• 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-amino-4'-fluoro-(1,1'-biphenyl)-4-carbonitrile
• 英文别名: 3-Amino-4'-fluorobiphenyl-4-carbonitrile；2-amino-4-(4-fluorophenyl)benzonitrile
• CAS: 1197199-76-0
• 化学式: C₁₃H₉FN₂
• 分子量: 212.226
• InChiKey: NNRIHWSYVLLLQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 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：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-amino-4'-fluoro-(1,1'-biphenyl)-4-carbonitrile 在 盐酸 、 氯化亚砜 、 水 、 potassium carbonate 、 N,N-二甲基甲酰胺 作用下， 以 甲乙醚 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 N-(7-[4-fluorophenyl]quinazolin-4-yl)-4-((1-(phenylthio)ethan-2-yl)amino)-3-nitrobenzenesulfonamide
  参考文献：
  名称：

  Quinazoline Sulfonamides as Dual Binders of the Proteins B-Cell Lymphoma 2 and B-Cell Lymphoma Extra Long with Potent Proapoptotic Cell-Based Activity

  摘要：

  ABT-737 and ABT-263 are potent inhibitors of the BH3 antiapoptotic proteins, Bcl-x(L) and Bcl-2. This class of putative anticancer agents invariantly contains an acylsulfonamide core. We have designed and synthesized a series of novel quinazoline-based inhibitors of Bcl-2 and Bcl-xL that contain a heterocyclic alternative to the acylsulfonamide. These compounds exhibit submicromolar, mechanism-based activity in human small-cell lung carcinoma cell lines in the presence of 10% human serum. This comprises the first successful demonstration of a quinazoline sulfonamide core serving as an effective benzoylsulfonamide bioisostere. Additionally, these novel quinazolines comprise only the second known class of Bcl-2 family protein inhibitors to induce mechanism-based cell death.

  DOI：

  10.1021/jm101596e
• 作为产物：
  描述：

  2-氨基-4-氯苯腈 、 4-氟苯硼酸 在 二氯双[二叔丁基-(4-二甲基氨基苯基)膦]钯(II) 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以64 %的产率得到3-amino-4'-fluoro-(1,1'-biphenyl)-4-carbonitrile
  参考文献：
  名称：

  [EN] 2-PYRAZOLE ANILINES AND RELATED ANALOGS FOR INHIBITING YAP/TAZ-TEAD
  [FR] 2-PYRAZOLE ANILINES ET ANALOGUES APPARENTÉS POUR INHIBER YAP/TAZ-TEAD

  摘要：

  The present disclosure relates to novel compounds, to said compounds for use as a medicine, more in particular for the prevention or treatment of diseases mediated by activity of YAP/TAZ-TEAD transcription, yet more in particular for the prevention or treatment of cancer or fibrosis. The present disclosure also relates to a method for the prevention or treatment of said diseases comprising the use of the novel compounds.

  公开号：

  WO2023122780A2

文献信息

• [EN] ARYLSULFONAMIDE COMPOUNDS, COMPOSITIONS AND METHODS OF USE<br/>[FR] COMPOSÉS ARYLSULFONAMIDES, COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：GENENTECH INC

  公开号：WO2009143246A3

  公开（公告）日：2010-04-29
• ARYLSULFONAMIDE COMPOUNDS, COMPOSITIONS AND METHODS OF USE
  申请人：Baell Jonathan Bayldon

  公开号：US20110098305A1

  公开（公告）日：2011-04-28

  Disclosed are compounds which inhibit the activity of anti-apoptotic protein family members, compositions containing the compounds and uses of the compounds for preparing medicaments for treating diseases during which occurs expression one or more than one of an anti-apoptotic protein family member.
• [EN] 2-PYRAZOLE ANILINES AND RELATED ANALOGS FOR INHIBITING YAP/TAZ-TEAD<br/>[FR] 2-PYRAZOLE ANILINES ET ANALOGUES APPARENTÉS POUR INHIBER YAP/TAZ-TEAD
  申请人：[en]THE KATHOLIEKE UNIVERSITEIT LEUVEN

  公开号：WO2023122780A2

  公开（公告）日：2023-06-29

  The present disclosure relates to novel compounds, to said compounds for use as a medicine, more in particular for the prevention or treatment of diseases mediated by activity of YAP/TAZ-TEAD transcription, yet more in particular for the prevention or treatment of cancer or fibrosis. The present disclosure also relates to a method for the prevention or treatment of said diseases comprising the use of the novel compounds.
• Quinazoline Sulfonamides as Dual Binders of the Proteins B-Cell Lymphoma 2 and B-Cell Lymphoma Extra Long with Potent Proapoptotic Cell-Based Activity
  作者：Brad E. Sleebs、Peter E. Czabotar、Wayne J. Fairbrother、W. Douglas Fairlie、John A. Flygare、David C. S. Huang、Wilhelmus J. A. Kersten、Michael F. T. Koehler、Guillaume Lessene、Kym Lowes、John P. Parisot、Brian J. Smith、Morey L. Smith、Andrew J. Souers、Ian P. Street、Hong Yang、Jonathan B. Baell

  DOI：10.1021/jm101596e

  日期：2011.3.24

  ABT-737 and ABT-263 are potent inhibitors of the BH3 antiapoptotic proteins, Bcl-x(L) and Bcl-2. This class of putative anticancer agents invariantly contains an acylsulfonamide core. We have designed and synthesized a series of novel quinazoline-based inhibitors of Bcl-2 and Bcl-xL that contain a heterocyclic alternative to the acylsulfonamide. These compounds exhibit submicromolar, mechanism-based activity in human small-cell lung carcinoma cell lines in the presence of 10% human serum. This comprises the first successful demonstration of a quinazoline sulfonamide core serving as an effective benzoylsulfonamide bioisostere. Additionally, these novel quinazolines comprise only the second known class of Bcl-2 family protein inhibitors to induce mechanism-based cell death.