N-(4-aminophenyl)-3,4-difluorobenzamide | 1016752-48-9

• 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-(4-aminophenyl)-3,4-difluorobenzamide
• 英文别名: N-(4-Aminophenyl)-3,4-difluoro-benzamide
• CAS: 1016752-48-9
• 化学式: C₁₃H₁₀F₂N₂O
• mdl: MFCD09802500
• 分子量: 248.232
• InChiKey: AWSXQCXSDONVDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 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：
  55.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-aminophenyl)-3,4-difluorobenzamide 、 2,3,4,5-四氟苯甲酸 在 三乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以63%的产率得到N-(4-(3,4-difluorobenzamido)phenyl)-2,3,4,5-tetrafluorobenzamide
  参考文献：
  名称：

  Amide derivatives of Gallic acid: Design, synthesis and evaluation of inhibitory activities against in vitro α-synuclein aggregation

  摘要：

  Gallic acid (GA), a natural phenolic acid, has received numerous attention because of its anti-oxidative, anti-inflammatory, and anti-cancer activity. More importantly, GA can act as an efficient inhibitor of alpha-Synuclein (alpha-Syn) aggregation at early stages. Nevertheless, some evidences suggest that GA is unlikely to cross the blood-brain barrier because of its high hydrophilicity. Hence, GA may not be considered as a promising candidate or entering brain and directly affecting the central nervous system. Accordingly, we have designed and synthesized a series of amide derivatives of GA, some of which possess appropriate lipophilicity and hydrophilicity with LogP (2.09-2.79). Meanwhile, these sheet-like conjugated compounds have good pi-electron delocalization and high ability of hydrogen-bond formation. Some compounds have shown better in vitro anti-aggregation activities than GA towards alpha-Syn, with IC50, down to 0.98 mu M. The valid modification strategy of GA is considered an efficient way to discover novel inhibitors of alpha-Syn aggregation.

  DOI：

  10.1016/j.bmc.2020.115596
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 N-(4-aminophenyl)-3,4-difluorobenzamide
  参考文献：
  名称：

  SAR and evaluation of novel 5H-benzo[c][1,8]naphthyridin-6-one analogs as Aurora kinase inhibitors

  摘要：

  Several potent Aurora kinase inhibitors derived from 5H-benzo[c][1,8]naphthyridin-6-one scaffold were identified. A crystal structure of Aurora kinase A in complex with an initial hit revealed a binding mode of the inhibitor within the ATP binding site and provided insight for structure-guided compound optimization. Subsequent SAR campaign provided a potent and selective pan Aurora inhibitor, which demonstrated potent target modulation and antiproliferative effects in the pancreatic cell line, MIAPaCa-2. Furthermore, this compound inhibited phosphorylation of histone H3 (pHH3) in mouse bone morrow upon oral administration, which is consistent with inhibition of Aurora kinase B activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.008

文献信息

• [EN] PROTEIN KINASE INHIBITORS AND USE THEREOF<br/>[FR] INHIBITEURS DE PROTÉINE KINASE ET LEUR UTILISATION
  申请人：MERCK SERONO SA

  公开号：WO2009108670A1

  公开（公告）日：2009-09-03

  Disclosed are benzonaphthyridinyl derivative compounds and analogs thereof, pharmaceutical compositions comprising such compounds and processes for preparing the same. The compounds are useful in the treatment of diseases amenable to kinase signal transduction inhibition, regulation or modulation.

  揭示了苯并萘啶衍生物化合物及其类似物，包括含有这些化合物的药物组合物以及制备这些化合物的方法。这些化合物在治疗对激酶信号传导抑制、调节或调控敏感的疾病中很有用。
• PROTEIN KINASE INHIBITORS AND USE THEREOF
  申请人：Huck Bayard R.

  公开号：US20110053906A1

  公开（公告）日：2011-03-03

  Disclosed are benzonaphthyridinyl derivative compounds and analogs thereof, pharmaceutical compositions comprising such compounds and processes for preparing the same. The compounds are useful in the treatment of diseases amenable to kinase signal transduction inhibition, regulation or modulation.

  本发明揭示了苯并萘啉衍生物化合物及其类似物，包括含有这些化合物的制药组合物和制备这些化合物的过程。这些化合物可用于治疗易于激酶信号传导抑制、调节或调控的疾病。
• NAPHTHYRIDINONES AS PROTEIN KINASE INHIBITORS
  申请人：Xiao Yufang

  公开号：US20110269758A1

  公开（公告）日：2011-11-03

  Naphthyridinone derivative compounds that inhibit Aurora kinase enzymes are disclosed along with pharmaceutical compositions comprising these compounds and methods for synthesizing the same. Such compounds have utility in the treatment of proliferative diseases resulting from unregulated and/or disturbed Aurora kinases such as cancers, psoriasis, viral and bacterial infections, inflammatory and autoimmune diseases.

  本发明揭示了抑制Aurora激酶酶的萘啶酮衍生物化合物，以及包含这些化合物的制药组合物和合成这些化合物的方法。这些化合物在治疗由未调节和/或扰动的Aurora激酶引起的增殖性疾病中具有实用性，如癌症、银屑病、病毒和细菌感染、炎症性和自身免疫性疾病。
• Protein kinase inhibitors and use thereof
  申请人：Huck Bayard R.

  公开号：US08735584B2

  公开（公告）日：2014-05-27

  Disclosed are benzonaphthyridinyl derivative compounds and analogs thereof, pharmaceutical compositions comprising such compounds and processes for preparing the same. The compounds are useful in the treatment of diseases amenable to kinase signal transduction inhibition, regulation or modulation.

  本发明涉及苯并萘啶衍生物化合物及其类似物，包括含有这些化合物的药物组合物以及制备这些化合物的方法。这些化合物在治疗易受激酶信号转导抑制、调节或调制的疾病中很有用。
• プロテインキナーゼ阻害剤としてのナフチリジノン
  申请人：メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング

  公开号：JP2011526912A

  公开（公告）日：2011-10-20

  オーロラ・キナーゼ酵素を阻害するナフチリジノン誘導体化合物が、これらの化合物を含んでなる医薬組成物及びこれらの化合物の合成方法と共に開示される。かかる化合物には、癌、乾癬、ウイルスや細菌の感染症、炎症性疾患及び自己免疫疾患などの無秩序な及び／又は障害のあるオーロラ・キナーゼに起因する増殖性疾患の処置における有用性がある。

  本研究公开了抑制极光激酶的萘啶酮衍生物化合物，以及含有这些化合物的药物组合物和合成这些化合物的方法。这些化合物可用于治疗由极光激酶紊乱和/或受损引起的增殖性疾病，如癌症、牛皮癣、病毒和细菌感染、炎症性疾病和自身免疫性疾病。