N-(2,6-difluorophenyl)-2-methyl-6-nitrobenzamide | 936025-14-8

• 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: N-(2,6-difluorophenyl)-2-methyl-6-nitrobenzamide
• 英文别名: N-(2,6-difluoro-phenyl)-2-methyl-6-nitro-benzamide
• CAS: 936025-14-8
• 化学式: C₁₄H₁₀F₂N₂O₃
• 分子量: 292.242
• InChiKey: PKGGSXFYHSOKMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 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：
  74.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2,6-difluorophenyl)-2-methyl-6-nitrobenzamide 在 双(三甲基硅烷基)氨基钾 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 2.42h， 生成 tert-butyl (S)-1-(3-(2,6-difluorophenyl)-5-methyl-4-oxo-3,4-dihydroquinazolin-2-yl)ethylcarbamate
  参考文献：
  名称：

  A Novel Highly Stereoselective Synthesis of 2,3-Disubstituted 3H-Quinazoline-4-one Derivatives

  摘要：

  An efficient three-step synthesis of chiral 3H-quinazoline-4-one derivatives from commercial materials is disclosed. The Mumm reaction of imidoyl chloride with alpha-amino acids followed by reductive cyclization affords enantiomerically pure (ee > 93%) quinazoline-4-ones in good overall yield. A comparison with existing approaches indicates that this method is superior for hindered substrates.

  DOI：

  10.1021/ol070276c
• 作为产物：
  描述：

  2-甲基-6-硝基苯甲酸 在 氯化亚砜 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 2.0h， 生成 N-(2,6-difluorophenyl)-2-methyl-6-nitrobenzamide
  参考文献：
  名称：

  A Novel Highly Stereoselective Synthesis of 2,3-Disubstituted 3H-Quinazoline-4-one Derivatives

  摘要：

  An efficient three-step synthesis of chiral 3H-quinazoline-4-one derivatives from commercial materials is disclosed. The Mumm reaction of imidoyl chloride with alpha-amino acids followed by reductive cyclization affords enantiomerically pure (ee > 93%) quinazoline-4-ones in good overall yield. A comparison with existing approaches indicates that this method is superior for hindered substrates.

  DOI：

  10.1021/ol070276c

文献信息

• Quinazolinones as Inhibitors of Human Phosphatidylinositol 3-Kinase Delta
  申请人：Fowler Kerry W.

  公开号：US20080275067A1

  公开（公告）日：2008-11-06

  Compounds that inhibit PI3Kδ activity, including compounds that selectively inhibit PI3Kδ activity, are disclosed. Methods of inhibiting phosphatidylinositol 3-kinase delta isoform (PI3Kδ) activity, and methods of treating diseases, such as disorders of immunity and inflammation in which PI3Kδ plays a role in leukocyte function, using the compounds also are disclosed.

  本发明公开了抑制PI3Kδ活性的化合物，包括选择性抑制PI3Kδ活性的化合物。本发明还公开了通过使用这些化合物来抑制磷脂酰肌醇3-激酶δ亚型（PI3Kδ）活性的方法，以及使用这些化合物来治疗疾病的方法，例如免疫和炎症紊乱，其中PI3Kδ在白细胞功能中发挥作用。
• QUINAZOLINONES AS INHIBITORS OF HUMAN PHOSPHATIDYLINOSITOL 3-KINASE DELTA
  申请人：Fowler Kerry W.

  公开号：US20100256168A1

  公开（公告）日：2010-10-07

  Compounds that inhibit PI3Kδ activity, including compounds that selectively inhibit PI 3 Kδ activity, are disclosed. Methods of inhibiting phosphatidylinositol 3-kinase delta isoform (PI3Kδ) activity, and methods of treating diseases, such as disorders of immunity and inflammation in which PI3Kδ plays a role in leukocyte function, using the compounds also are disclosed.

  本发明公开了抑制PI3Kδ活性的化合物，其中包括选择性抑制PI3Kδ活性的化合物。本发明还公开了抑制磷脂酰肌醇3-激酶δ亚型（PI3Kδ）活性的方法，以及使用这些化合物治疗疾病的方法，例如免疫和炎症紊乱，其中PI3Kδ在白细胞功能中发挥作用。
• Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta
  申请人：ICOS Corporation

  公开号：US08207153B2

  公开（公告）日：2012-06-26

  Compounds that inhibit P13Kδ activity, including compounds that selectively inhibit P13Kδ activity, are disclosed. Methods of inhibiting phosphatidylinositol 3-kinase delta isoform (P13Kδ) activity, and methods of treating diseases, such as disorders of immunity and inflammation in which P13Kδ plays a role in leukocyte function, using the compounds also are disclosed.

  本文公开了抑制P13Kδ活性的化合物，包括选择性抑制P13Kδ活性的化合物。还公开了抑制磷脂酰肌醇3-激酶δ亚型（P13Kδ）活性的方法，以及使用这些化合物治疗疾病的方法，例如P13Kδ在白细胞功能中发挥作用的免疫和炎症紊乱。
• 6-fluoro-3-phenyl-2-[1-(9H-purin-6-ylamino)-ethyl]-3H-quinazolin-4-one as an inhibitor of human phosphatidylinositol 3-kinase delta
  申请人：Icos Corporation

  公开号：US08779131B2

  公开（公告）日：2014-07-15

  Compounds that inhibit PI3Kδ activity, including compounds that selectively inhibit PI3Kδ activity, are disclosed. Methods of inhibiting phosphatidylinositol 3-kinase delta isoform (PI3Kδ) activity, and methods of treating diseases, such as disorders of immunity and inflammation in which PI3Kδ plays a role in leukocyte function, using the compounds also are disclosed. An exemplary compound disclosed in this application is shown below.

  本申请公开了抑制PI3Kδ活性的化合物，包括选择性抑制PI3Kδ活性的化合物。本申请还公开了抑制磷脂酰肌醇3-激酶δ亚型（PI3Kδ）活性的方法，以及使用这些化合物治疗疾病的方法，例如，PI3Kδ在白细胞功能中发挥作用的免疫和炎症紊乱。本申请公开的一个示例化合物如下图所示。
• 6-fluoro-3-phenyl-2-[1-(9H-purin-6-ylamino)ethyl]-3H-quinazolin-4-one as an inhibitor of human phosphatidylinositol 3-kinase delta
  申请人：ICOS Corporation

  公开号：US08586597B2

  公开（公告）日：2013-11-19

  Compounds that inhibit PI3Kδ activity, including compounds that selectively inhibit PI3Kδ activity, are disclosed. Methods of inhibiting phosphatidylinositol 3-kinase delta isoform PI3Kδ activity, and methods of treating diseases, such as disorders of immunity and inflammation in which PI3Kδ plays a role in leukocyte function, using the compounds also are disclosed. An exemplary compound disclosed in this application is shown below.

  本文披露了抑制PI3Kδ活性的化合物，包括选择性抑制PI3Kδ活性的化合物。还披露了通过使用这些化合物来抑制磷脂酰肌醇3-激酶δ亚型PI3Kδ的活性以及治疗疾病的方法，例如免疫和炎症紊乱，其中PI3Kδ在白细胞功能中发挥作用。本申请中披露的一种示例化合物如下所示。