4-(2,4-difluorophenyl)pyrimidine | 1187176-51-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-(2,4-difluorophenyl)pyrimidine
• 英文别名: 4-DFPPM
• CAS: 1187176-51-7
• 化学式: C₁₀H₆F₂N₂
• 分子量: 192.168
• InChiKey: FLIRESNEIHJYNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  277.2±25.0 °C(Predicted)
• 密度：
  1.284±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 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：
  25.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2,4-difluorophenyl)pyrimidine 在 ferrous(II) sulfate heptahydrate 、 氯化亚砜 、 硫酸 、 双氧水 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 N-(3-fluoro-4-(6-methoxy-7-(3-morpholinopropoxy)quinolin-4-yloxy)phenyl)-4-(2,4-difluorophenyl)pyrimidine-2-carboxamide
  参考文献：
  名称：

  Design, synthesis, and structure–activity relationships of novel 6,7-disubstituted-4-phenoxyquinoline derivatives as potential antitumor agents

  摘要：

  Two series of quinoline derivatives bearing the pyridine/pyrimidine scaffold were synthesized, and evaluated for their c-Met kinase inhibitory activity and antiproliferative activity against 5 cancer cell lines (HT-29, H460, MKN-45, A549, and U87MG) were evaluated in vitro. Most compounds showed moderate to excellent potency, and compared to foretinib, the most promising analog 18b (c-Met half-maximal inhibitory concentration [IC50] = 1.39 nM) showed a 7.3-fold increase in activity against HT-29 cell line in vitro. Structure activity relationship studies indicated that regulation of the electron density on the pyridine/pyrimidine ring to a proper degree was a key factor in improving the antitumor activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.019
• 作为产物：
  描述：

  2',4'-二氟苯乙酮 在 sodium ethanolate 作用下， 以 乙醇 、 二甲胺 为溶剂， 生成 4-(2,4-difluorophenyl)pyrimidine
  参考文献：
  名称：

  Design, synthesis, and structure–activity relationships of novel 6,7-disubstituted-4-phenoxyquinoline derivatives as potential antitumor agents

  摘要：

  Two series of quinoline derivatives bearing the pyridine/pyrimidine scaffold were synthesized, and evaluated for their c-Met kinase inhibitory activity and antiproliferative activity against 5 cancer cell lines (HT-29, H460, MKN-45, A549, and U87MG) were evaluated in vitro. Most compounds showed moderate to excellent potency, and compared to foretinib, the most promising analog 18b (c-Met half-maximal inhibitory concentration [IC50] = 1.39 nM) showed a 7.3-fold increase in activity against HT-29 cell line in vitro. Structure activity relationship studies indicated that regulation of the electron density on the pyridine/pyrimidine ring to a proper degree was a key factor in improving the antitumor activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.019

文献信息

• NOVEL IODO PYRIMIDINE DERIVATIVES USEFUL FOR THE TREATMENT OF MACROPHAGE MIGRATION INHIBITORY FACTOR (MIF)-IMPLICATED DISEASES AND CONDITIONS
  申请人：University Of Louisville Research Foundation, Inc.

  公开号：EP2480235A2

  公开（公告）日：2012-08-01
• [EN] NOVEL IODO PYRIMIDINE DERIVATIVES USEFUL FOR THE TREATMENT OF MACROPHAGE MIGRATION INHIBITORY FACTOR (MIF)-IMPLICATED DISEASES AND CONDITIONS<br/>[FR] NOUVEAUX DÉRIVÉS D'IODO PYRIMIDINES UTILES POUR LE TRAITEMENT DE MALADIES OU AFFECTIONS LIÉES AU FACTEUR INHIBITEUR DE LA MIGRATION DES MACROPHAGES
  申请人：UNIV LOUISVILLE RES FOUND

  公开号：WO2011038234A2

  公开（公告）日：2011-03-31

  Compounds useful for the inhibition of macrophage migration inhibitory factor (MIF) are provided herein, having the Formula (I): wherein A is selected from the group consisting of aromatic or non-aromatic rings, bicyclic rings, polycyclic rings, alkenes or alkynes; B is H, OH, OR, SR, NH2, NHR, or alkyl; R is H or alkyl, and X and Y are independently N or CH, but one of X and Y must be N. Also provided are pharmaceutical compositions comprising a Formula I compound and methods for the treatment of MIF-implicated diseases or conditions, comprising administering a safe and effective amount of a Formula I compound.