6-bromo-N-(3-(trifluoromethyl)phenyl)quinazolin-4-amine | 307538-27-8

• 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-(3-(trifluoromethyl)phenyl)quinazolin-4-amine
• 英文别名: 6-bromo-N-[3-(trifluoromethyl)phenyl]quinazolin-4-amine
• CAS: 307538-27-8
• 化学式: C₁₅H₉BrF₃N₃
• 分子量: 368.156
• InChiKey: DSKPAROKUPBYQP-UHFFFAOYSA-N

物化性质

• 沸点：
  423.1±45.0 °C(Predicted)
• 密度：
  1.630±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  37.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-bromo-N-(3-(trifluoromethyl)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， 生成 6-(thiazol-5-yl)-N-(3-(trifluoromethyl)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
• 作为产物：
  描述：

  6-溴-4-氯喹唑啉 、 间氨基三氟甲苯 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 0.25h， 生成 6-bromo-N-(3-(trifluoromethyl)phenyl)quinazolin-4-amine
  参考文献：
  名称：

  Discovery and SAR of 6-substituted-4-anilinoquinazolines as non-competitive antagonists of mGlu5

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2009.10.024

文献信息

• 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.
• Discovery, Synthesis, and Biological Evaluation of Thiazoloquin(az)olin(on)es as Potent CD38 Inhibitors
  作者：Curt D. Haffner、J. David Becherer、Eric E. Boros、Rodolfo Cadilla、Tiffany Carpenter、David Cowan、David N. Deaton、Yu Guo、Wallace Harrington、Brad R. Henke、Michael R. Jeune、Istvan Kaldor、Naphtali Milliken、Kim G. Petrov、Frank Preugschat、Christie Schulte、Barry G. Shearer、Todd Shearer、Terrence L. Smalley、Eugene L. Stewart、J. Darren Stuart、John C. Ulrich

  DOI：10.1021/jm502009h

  日期：2015.4.23

  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.