2-(4-fluoro-benzylsulfanyl)-3H-quinazolin-4-one | 449745-75-9

• 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: 2-(4-fluoro-benzylsulfanyl)-3H-quinazolin-4-one
• 英文别名: 2-[(4-fluorobenzyl)thio]quinazolin-4(3H)-one；2-[(4-Fluorobenzyl)sulfanyl]quinazolin-4-ol；2-[(4-fluorophenyl)methylsulfanyl]-3H-quinazolin-4-one
• CAS: 449745-75-9
• 化学式: C₁₅H₁₁FN₂OS
• 分子量: 286.33
• InChiKey: OYZOEJGJGNDJBL-UHFFFAOYSA-N

物化性质

• 沸点：
  457.5±47.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-fluoro-benzylsulfanyl)-3H-quinazolin-4-one 在 劳森试剂 、 盐酸 、 水 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 30.0h， 生成 2-[(4-fluorophenyl)methylsulfanyl]-4-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methylsulfanyl]quinazoline
  参考文献：
  名称：

  Synthesis and evaluation of quinazoline derivatives as phosphodiesterase 7 inhibitors

  摘要：

  The latest scientific findings concerning PDE7 and PDE4 inhibition suggest that selective small-molecule inhibitors of both enzymes could provide a novel approach to treat a variety of immunological diseases. In this context, we describe a new series of quinazoline derivatives from quinazolin-4-thiones which include a substituted biphenyl fragment. Some of these compounds show inhibitory potencies at sub-micromolar levels against the catalytic domain of PDE7. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.067
• 作为产物：
  描述：

  4-氟溴苄 、 2-巯基-4(3H)-喹唑酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以65%的产率得到2-(4-fluoro-benzylsulfanyl)-3H-quinazolin-4-one
  参考文献：
  名称：

  Synthesis and evaluation of quinazoline derivatives as phosphodiesterase 7 inhibitors

  摘要：

  The latest scientific findings concerning PDE7 and PDE4 inhibition suggest that selective small-molecule inhibitors of both enzymes could provide a novel approach to treat a variety of immunological diseases. In this context, we describe a new series of quinazoline derivatives from quinazolin-4-thiones which include a substituted biphenyl fragment. Some of these compounds show inhibitory potencies at sub-micromolar levels against the catalytic domain of PDE7. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.067

文献信息

• Synthesis and evaluation of 2-substituted 4(3H)-quinazolinone thioether derivatives as monoamine oxidase inhibitors
  作者：Malikotsi A. Qhobosheane、Anél Petzer、Jacobus P. Petzer、Lesetja J. Legoabe

  DOI：10.1016/j.bmc.2018.09.032

  日期：2018.11

  In the present study, a series of fourteen 2-mercapto-4(3H)-quinazolinone derivatives was synthesised and evaluated as potential inhibitors of the human monoamine oxidase (MAO) enzymes. Quinazolinone is the oxidised form of quinazoline, and although this class has not yet been extensively explored as MAO inhibitors, it has been shown to possess a wide variety of biological activities. Among the quinazolinone

  在本研究中，合成了一系列十四个2-巯基-4（3 H）-喹唑啉酮衍生物，并将其评估为人单胺氧化酶（MAO）酶的潜在抑制剂。喹唑啉酮是喹唑啉的氧化形式，尽管该类作为MAO抑制剂尚未得到广泛研究，但已显示其具有多种生物学活性。在研究的喹唑啉酮衍生物中，有7种化合物（IC 50  <1 µM）被证明是有效的和特异性的MAO-B抑制剂，其中最有效的抑制剂是2-[（（3-碘苄基）硫代]喹唑啉-4（3 H）-一种显示的IC 50值为0.142μM。进一步的研究表明，该抑制剂是具有K的MAO-B的可逆和竞争性抑制剂。i值为0.068 µM。测试化合物均不是MAO-A抑制剂。对MAO-B抑制的构效关系（SAR）的分析表明，在喹唑啉酮的C2位上被在间位上带有Cl，Br或I的苄硫基部分取代，产生了该系列中最有效的抑制剂。相反，用未取代的苄硫基部分（IC 50  ＝3.03μM）取代导致对MAO-B的抑制活性明显
• Synthesis and evaluation of quinazoline derivatives as phosphodiesterase 7 inhibitors
  作者：Ana I. Sánchez、Valentín Martínez-Barrasa、Carolina Burgos、Juan J. Vaquero、Julio Alvarez-Builla、Emma Terricabras、Víctor Segarra

  DOI：10.1016/j.bmc.2013.01.067

  日期：2013.4

  The latest scientific findings concerning PDE7 and PDE4 inhibition suggest that selective small-molecule inhibitors of both enzymes could provide a novel approach to treat a variety of immunological diseases. In this context, we describe a new series of quinazoline derivatives from quinazolin-4-thiones which include a substituted biphenyl fragment. Some of these compounds show inhibitory potencies at sub-micromolar levels against the catalytic domain of PDE7. (C) 2013 Elsevier Ltd. All rights reserved.