6-bromo-N-phenyl quinazolin-4-amine | 307529-03-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 6-bromo-N-phenyl quinazolin-4-amine
• 英文别名: 6-bromo-N-phenylquinazolin-4-amine
• CAS: 307529-03-9
• 化学式: C₁₄H₁₀BrN₃
• 分子量: 300.157
• InChiKey: RQFAJYPCPZEVHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-bromo-N-phenyl quinazolin-4-amine 、 三丁基噻唑-5-锡 在 copper(l) iodide 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以32 mg的产率得到N-phenyl-6-(thiazol-5-yl)quinazolin-4-amine
  参考文献：
  名称：

  Discovery, Synthesis, and Biological Evaluation of Thiazoloquin(az)olin(on)es as Potent CD38 Inhibitors

  摘要：

  A series of thiazoloquin(az)olinones were synthesized and found to have potent inhibitory activity against CD38. Several of these compounds were also shown to have good pharmacokinetic properties and demonstrated the ability to elevate NAD levels in plasma, liver, and muscle tissue. In particular, compound 78c was given to diet induced obese (DIO) C57Bl6 mice, elevating NAD > 5-fold in liver and >1.2-fold in muscle versus control animals at a 2 h time point. The compounds described herein possess the most potent CD38 inhibitory activity of any small molecules described in the literature to date. The inhibitors should allow for a more detailed assessment of how NAD elevation via CD38 inhibition affects physiology in NAD deficient states.

  DOI：

  10.1021/jm502009h
• 作为产物：
  描述：

  6-溴-4-氯喹唑啉 、 苯胺 以 乙腈 为溶剂， 以1.05 g的产率得到6-bromo-N-phenyl quinazolin-4-amine
  参考文献：
  名称：

  Discovery, Synthesis, and Biological Evaluation of Thiazoloquin(az)olin(on)es as Potent CD38 Inhibitors

  摘要：

  A series of thiazoloquin(az)olinones were synthesized and found to have potent inhibitory activity against CD38. Several of these compounds were also shown to have good pharmacokinetic properties and demonstrated the ability to elevate NAD levels in plasma, liver, and muscle tissue. In particular, compound 78c was given to diet induced obese (DIO) C57Bl6 mice, elevating NAD > 5-fold in liver and >1.2-fold in muscle versus control animals at a 2 h time point. The compounds described herein possess the most potent CD38 inhibitory activity of any small molecules described in the literature to date. The inhibitors should allow for a more detailed assessment of how NAD elevation via CD38 inhibition affects physiology in NAD deficient states.

  DOI：

  10.1021/jm502009h

文献信息

• Substituted 4-Amino-Quinazoline Compounds with Metabotropic Glutamate Receptor Regulating Activity and Uses Thereof
  申请人：REICH Melanie

  公开号：US20090069320A1

  公开（公告）日：2009-03-12

  Substituted 4-amino-quinazoline compounds corresponding to formula I methods for their production, pharmaceutical compositions containing these compounds as active agents, and the uses thereof for treating or inhibiting disorders or disease states.

  根据公式I的4-氨基喹唑啉化合物替代物，其生产方法，含有这些化合物的药物组合物以及用于治疗或抑制疾病状态或疾病状态的用途。
• Synthesis of Fused Polycyclic 4‐Anilinoquinazolines and <i>N</i> ‐Quinazoline‐Indoles <i>via</i> Selective C−H Bond Activation
  作者：Xin‐Yang Liu、Hao Liu、Xian‐Zhang Liao、Lin Dong、Fen‐Er Chen

  DOI：10.1002/adsc.202000895

  日期：2020.12.22

  An efficient rhodium(III)‐catalyzed site‐selective functionalization of 4‐anilinoquinazolines offers exciting possibilities for fused polycyclic 4‐anilinoquinazoline derivatives and N‐quinazoline‐indoles by using diazo compounds as the elegant coupling partners. This one‐pot cascade approach to establish various complex 4‐anilinoquinazoline units with potential biological activities only depends on

  通过使用重氮化合物作为优雅的偶联伙伴，高效的铑（III）催化4-苯胺基喹唑啉的位点选择性官能化为稠合多环4-苯胺基喹唑啉衍生物和N-喹唑啉吲哚提供了令人兴奋的可能性。这种单罐级联方法可以建立具有潜在生物活性的各种复杂的4-苯胺基喹唑啉单元，仅取决于底物和添加剂。
• Discovery and SAR of 6-substituted-4-anilinoquinazolines as non-competitive antagonists of mGlu5
  作者：Andrew S. Felts、Sam A. Saleh、Uyen Le、Alice L. Rodriguez、C. David Weaver、P. Jeffrey Conn、Craig W. Lindsley、Kyle A. Emmitte

  DOI：10.1016/j.bmcl.2009.10.024

  日期：2009.12

  A high-throughput cell-based screen identified a series of 6-substituted-4-anilinoquinazolines as noncompetitive antagonists of metabotropic glutamate receptor 5 (mGlu(5)). This Letter describes the SAR of this series and the profile of selected compounds in selectivity and radioligand binding assays. (C) 2009 Elsevier Ltd. All rights reserved.
• COMPOUNDS WHICH SPECIFICALLY BIND TO CD38 FOR USE IN THE TREATMENT OF NEURODEGENERATIVE AND INFLAMMATORY DISEASES
  申请人：ENCEFA

  公开号：EP3658586A1

  公开（公告）日：2020-06-03
• [DE] SUBSTITUIERTE 4-AMINO-CHINAZOLIN-DERIVATE ALS REGULATOREN VON METAB0TR0PISCHEN GLUTAMATREZEPTOREN UND IHRE VERWENDUNG ZUR HERSTELLUNG VON ARZNEIMITTELN<br/>[EN] SUBSTITUTED 4-AMINO-QUINAZOLINE DERIVATIVES AS REGULATORS OF METABOTROPIC GLUTAMATE RECEPTORS AND THEIR USE FOR PRODUCING DRUGS<br/>[FR] DÉRIVÉS DE 4-AMINO-CHINAZOLINE SUBSTITUÉS SERVANT DE RÉGULATEURS DE RÉCEPTEURS DE GLUTAMATE MÉTABOTROPIQUES ET UTILISATION DANS LA FABRICATION DE MÉDICAMENTS
  申请人：GRUENENTHAL GMBH

  公开号：WO2007104560A1

  公开（公告）日：2007-09-20

  [EN] The invention relates to substituted 4-amino-quinazoline derivatives of formula (I), to methods for producing them, to drugs containing said compounds and to their use for producing drugs.
  [FR] L'invention concerne des dérivés de 4-amino-chinazoline substitués représentés par la formule (I), des procédés de fabrication de ces dérivés, des médicaments les contenant et leur utilisation dans la fabrication de médicaments.
  [DE] Die vorliegende Erfindung betrifft substituierte 4-Amino-chinazolin-Derivate der allgemeinen Formel (I). Verfahren zu ihrer Herstellung, Arzneimittel enthaltend diese Verbindungen sowie deren Verwendung zur Herstellung von Arzneimitteln.