(2-aminophenyl)(3,4-difluorophenyl)methanone | 1103586-40-8

• 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: (2-aminophenyl)(3,4-difluorophenyl)methanone
• 英文别名: (2-Aminophenyl)-(3,4-difluorophenyl)methanone
• CAS: 1103586-40-8
• 化学式: C₁₃H₉F₂NO
• 分子量: 233.217
• InChiKey: GGWLNQOFRZUBOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 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：
  43.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-aminophenyl)(3,4-difluorophenyl)methanone 在 potassium hydroxide 、 肼 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.21h， 生成 3-[5-(4-chlorophenyl)-4,5-dihydro-1H-pyrazol-3-yl]-4-(3,4-difluorophenyl)quinolin-2(1H)-one
  参考文献：
  名称：

  Structure–Activity Relationships and Pharmacophore Model of a Noncompetitive Pyrazoline Containing Class of GluN2C/GluN2D Selective Antagonists

  摘要：

  Here we describe the synthesis and structure-activity relationship for a class of pyrazoline-containing dihydroquinolone negative allosteric modulators of the NMDA receptor that show strong subunit selectivity for GluN2C- and GluN2D-containing receptors over GluN2A- and GluN2B-containing receptors. Several members of this class inhibit NMDA receptor responses in the nanomolar range and are more than 50-fold selective over GluN1/GluN2A and GluN1/GluN2B NMDA receptors, as well as AMPA, kainate, GABA, glycine, nicotinic, serotonin, and purinergic receptors. Analysis of the purified enantiomers of one of the more potent and selective compounds shows that the S-enantiomer is both more potent and more selective than the R-enantiomer. The S-enantiomer had an IC50 of 0.17-0.22 mu M at GluN2D- and GluN2C-containing receptors, respectively, and showed over 70-fold selectivity over other NMDA receptor subunits. The subunit selectivity of this class of compounds should be useful in defining the role of GluN2C- and GluN2D-containing receptors in specific brain circuits in both physiological and pathophysiological conditions.

  DOI：

  10.1021/jm400652r
• 作为产物：
  描述：

  靛红酸酐 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 2.17h， 生成 (2-aminophenyl)(3,4-difluorophenyl)methanone
  参考文献：
  名称：

  Structure–Activity Relationships and Pharmacophore Model of a Noncompetitive Pyrazoline Containing Class of GluN2C/GluN2D Selective Antagonists

  摘要：

  Here we describe the synthesis and structure-activity relationship for a class of pyrazoline-containing dihydroquinolone negative allosteric modulators of the NMDA receptor that show strong subunit selectivity for GluN2C- and GluN2D-containing receptors over GluN2A- and GluN2B-containing receptors. Several members of this class inhibit NMDA receptor responses in the nanomolar range and are more than 50-fold selective over GluN1/GluN2A and GluN1/GluN2B NMDA receptors, as well as AMPA, kainate, GABA, glycine, nicotinic, serotonin, and purinergic receptors. Analysis of the purified enantiomers of one of the more potent and selective compounds shows that the S-enantiomer is both more potent and more selective than the R-enantiomer. The S-enantiomer had an IC50 of 0.17-0.22 mu M at GluN2D- and GluN2C-containing receptors, respectively, and showed over 70-fold selectivity over other NMDA receptor subunits. The subunit selectivity of this class of compounds should be useful in defining the role of GluN2C- and GluN2D-containing receptors in specific brain circuits in both physiological and pathophysiological conditions.

  DOI：

  10.1021/jm400652r

文献信息

• Metal‐Free Synthesis of Anthranils by PhIO Mediated Heterocyclization of <i>ortho</i> ‐Carbonyl Anilines
  作者：Alankrita Garia、Jatin Grover、Nidhi Jain

  DOI：10.1002/ejoc.202100756

  日期：2021.8.6

  A metal-free synthesis of anthranils from ortho-carbonyl anilines using PhIO as a sole reagent under ambient conditions is described. No external additives are required, the reaction has broad substrate scope and delivers anthranils in excellent yields via oxidative heterocyclization.

  描述了在环境条件下使用 PhIO 作为唯一试剂从邻羰基苯胺无金属合成邻氨基苯甲酸。不需要外部添加剂，该反应具有广泛的底物范围，并通过氧化杂环化以优异的产率提供邻氨基苯甲酸。
• 2-Aminobenzophenones as a Novel Class of Bradykinin B₁Receptor Antagonists
  作者：Dai-Shi Su、John L. Lim、Elizabeth Tinney、Bang-Lin Wan、Kathy L. Murphy、Duane R. Reiss、C. Meacham Harrell、Stacy S. O’Malley、Rick W. Ransom、Raymond S. L. Chang、Douglas J. Pettibone、Jian Yu、Cuyue Tang、Thomayant Prueksaritanont、Roger M. Freidinger、Mark G. Bock、Neville J. Anthony

  DOI：10.1021/jm800199h

  日期：2008.7

  Selective bradykinin (BK) B 1 receptor antagonists could be novel therapeutic agents for the treatment of pain and inflammation. Elucidation of the structure activity relationships of the structurally novel HTS lead compound 1 provided potent hBK B 1 receptor antagonists with excellent receptor occupancy in the CNS of hBK B 1 transgenic rats.

  选择性缓激肽（BK）B 1受体拮抗剂可能是治疗疼痛和炎症的新型治疗剂。对结构新颖的HTS前导化合物1的结构活性关系的阐明提供了有效的hBK B 1受体拮抗剂，在hBK B 1转基因大鼠的中枢神经系统中具有出色的受体占有率。
• New analogues of camptothecin, their use as medicaments and the pharmaceutical compositions containing them
  申请人：——

  公开号：US20030004150A1

  公开（公告）日：2003-01-02

  A compound of the formula 1 wherein the substituents are defined as in the specification which compounds are useful in the treatment of cancer.

  其中取代基如规范中所定义的化合物的化学式，这些化合物在癌症治疗中很有用。
• Analogues optiquement purs de la camptothecine
  申请人：Société de Conseils de Recherches et d'Applications Scientifiques ( S.C.R.A.S.)

  公开号：EP1338599A1

  公开（公告）日：2003-08-27

  L'invention concerne notamment les composés de formule générale dans laquelle R1 représente un radical alkyle inférieur ; R2, R3, R4 et R5 représentent, indépendamment, H, un radical halo ou -OSO2R10 ; R6, R7, P8, R9 et R10 représentent divers groupes variables. Ces composés, inhibiteurs de topoisomérases, sont particulièrement intéressants en tant que médicaments anti-cancéreux.

  本发明尤其涉及通式如下的化合物 其中 R1 代表低级烷基；R2、R3、R4 和 R5 独立地代表 H、卤代基或 -OSO2R10；R6、R7、P8、R9 和 R10 代表各种可变基团。这些化合物是拓扑异构酶的抑制剂，作为抗癌药物特别令人感兴趣。
• ANALOGUES OPTIQUEMENT PURS DE LA CAMPTOTHECINE
  申请人：SOCIETE DE CONSEILS DE RECHERCHES ET D'APPLICATIONS SCIENTIFIQUES (S.C.R.A.S.)

  公开号：EP1165565A1

  公开（公告）日：2002-01-02