8-bromo-6-methyl-4-oxo-3-phenyl-2-thioxo-1,2,3,4-tetrahydroquinazoline | 1357082-30-4

• 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: 8-bromo-6-methyl-4-oxo-3-phenyl-2-thioxo-1,2,3,4-tetrahydroquinazoline
• 英文别名: 8-bromo-6-methyl-3-phenyl-2-sulfanylidene-1H-quinazolin-4-one
• CAS: 1357082-30-4
• 化学式: C₁₅H₁₁BrN₂OS
• 分子量: 347.235
• InChiKey: XUSPNKGURAYEMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氨基-3-溴-5-甲基苯甲酸 、 硫代异氰酸苯酯 以 乙腈 为溶剂， 反应 0.75h， 以55%的产率得到8-bromo-6-methyl-4-oxo-3-phenyl-2-thioxo-1,2,3,4-tetrahydroquinazoline
  参考文献：
  名称：

  Neuroprotective efficacy of quinazoline type phosphodiesterase 7 inhibitors in cellular cultures and experimental stroke model

  摘要：

  A simple and efficient synthetic method for the preparation of quinazoline type phosphodiesterase 7 (PDE7) inhibitors, based on microwave irradiation, has been developed. The use of this methodology improved yields and reaction times, providing a scalable procedure. These compounds are pharmacologically interesting because of their in vivo efficacy both in spinal cord injury and Parkinson's disease models, as shown in previous studies from our group. Herein we describe for the first time that administration of one of the PDE7 inhibitors here optimized, 3-pheny1-2,4-dithioxo-1,2,3,4-tetrahydroquinazoline (compound 5), ameliorated brain damage and improved behavioral outcome in a permanent middle cerebral artery occlusion (pMCAO) stroke model. Furthermore, we demonstrate that these PDE7 inhibitors are potent anti-inflammatory as well as neuroprotective agents in primary cultures of neural cells. These results led us to propose PDE7 inhibitors as a new class of therapeutic agents for neuroprotection. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.10.040

文献信息

• Neuroprotective efficacy of quinazoline type phosphodiesterase 7 inhibitors in cellular cultures and experimental stroke model
  作者：Miriam Redondo、Juan G. Zarruk、Placido Ceballos、Daniel I. Pérez、Concepción Pérez、Ana Perez-Castillo、María A. Moro、José Brea、Cristina Val、María I. Cadavid、María I. Loza、Nuria E. Campillo、Ana Martínez、Carmen Gil

  DOI：10.1016/j.ejmech.2011.10.040

  日期：2012.1

  A simple and efficient synthetic method for the preparation of quinazoline type phosphodiesterase 7 (PDE7) inhibitors, based on microwave irradiation, has been developed. The use of this methodology improved yields and reaction times, providing a scalable procedure. These compounds are pharmacologically interesting because of their in vivo efficacy both in spinal cord injury and Parkinson's disease models, as shown in previous studies from our group. Herein we describe for the first time that administration of one of the PDE7 inhibitors here optimized, 3-pheny1-2,4-dithioxo-1,2,3,4-tetrahydroquinazoline (compound 5), ameliorated brain damage and improved behavioral outcome in a permanent middle cerebral artery occlusion (pMCAO) stroke model. Furthermore, we demonstrate that these PDE7 inhibitors are potent anti-inflammatory as well as neuroprotective agents in primary cultures of neural cells. These results led us to propose PDE7 inhibitors as a new class of therapeutic agents for neuroprotection. (C) 2011 Elsevier Masson SAS. All rights reserved.