3-(2,6-difluorophenyl)-4-oxo-2-thioxo-1,2,3,4-tetrahydroquinazoline | 1039819-74-3

• 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: 3-(2,6-difluorophenyl)-4-oxo-2-thioxo-1,2,3,4-tetrahydroquinazoline
• 英文别名: 3-(2,6-Difluorophenyl)-2-sulfanylidene-1,2,3,4-tetrahydroquinazolin-4-one；3-(2,6-difluorophenyl)-2-sulfanylidene-1H-quinazolin-4-one
• CAS: 1039819-74-3
• 化学式: C₁₄H₈F₂N₂OS
• 分子量: 290.293
• InChiKey: PYTJFPPIDPMDLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  硫酸二乙酯 、 3-(2,6-difluorophenyl)-4-oxo-2-thioxo-1,2,3,4-tetrahydroquinazoline 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以58%的产率得到2-ethylthio-3-(2,6-difluorophenyl)-4-oxo-3,4-dihydroquinazoline
  参考文献：
  名称：

  S-SUBSTITUTED QUINAZOLINES AND THEIR THERAPEUTIC APPLICATIONS FOR THE TREATMENT OF DISEASES MEDIATED BY PDE7

  摘要：

  本发明涉及一类S-取代喹唑啉衍生物家族，它们是磷酸二酯酶7（PDE7）的抑制剂，用于治疗或预防由该酶介导的疾病，特别是炎症性、神经退行性、神经系统、精神和/或自身免疫性疾病。

  公开号：

  US20160340320A1
• 作为产物：
  描述：

  2,6-二氟异硫氰酸苯酯 、 邻氨基苯甲酸甲酯 以 水 、 二甲基亚砜 为溶剂， 反应 0.67h， 以60%的产率得到3-(2,6-difluorophenyl)-4-oxo-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

• COMPOUND THAT IS A DUAL INHIBITOR OF ENZYMES PDE7 AND/OR PDE4, PHARMACEUTICAL COMPOSITIONS AND USES THEREOF
  申请人：Gil Ayuso-Gontan Carmen

  公开号：US20100152213A1

  公开（公告）日：2010-06-17

  The invention relates to a series of dual inhibitors of enzymes PDE7 and PDE4, having formula (I) and to the use thereof in the production of pharmaceutical compositions for the treatment of inflammatory and/or autoimmune processes.

  本发明涉及一系列PDE7和PDE4酶的双重抑制剂，具有公式（I），以及在制备用于治疗炎症和/或自身免疫过程的药物组合物中使用它们的用途。
• USE OF QUINAZOLINE DERIVATIVES FOR NEURODEGENERATIVE DISEASES
  申请人：Consejo Superior de Investigaciones Cientificas (CSIC)

  公开号：EP2433637B9

  公开（公告）日：2015-06-10
• CODES, a novel procedure for ligand-based virtual screening: PDE7 inhibitors as an application example
  作者：Ana Castro、María José Jerez、Carmen Gil、Félix Calderón、Teresa Doménech、Arsenio Nueda、Ana Martínez

  DOI：10.1016/j.ejmech.2007.10.027

  日期：2008.7

  Phosphodiesterase (PDE) 7 is a high affinity cAMP-specific PDE whose functional role in T-cells has been the subject of some controversy. Recent findings on tissue distribution, however, support the hypothesis that PDE7 could be a good target for the treatment of airway diseases, T-cell related diseases or central nervous system (CNS) disorders. Therefore, the identification of selective inhibitors targeted against PDE7 enzyme has become an attractive area of research. We report here the first use of the descriptors generated by the CODES program for ligand-based virtual screening. This program codifies molecules from a topological point of view and the generated descriptors are related to the chemical nature of the atoms, the atomic bonds and the connectivity with the rest of the molecule. They are also able to distinguish among stereoisomers. By using this approach, 173 compounds were codified, and their similarity with the reference compound was analysed. Based on the analysis, new potential PDE7 inhibitors have been identified, synthesized and biologically evaluated confirming that CODES descriptors are valid for ligand-based virtual screening and provided new lead compounds for further optimization as potent and selective PDE7 inhibitors. (c) 2007 Elsevier Masson SAS. All rights reserved.
• US9192610B2
  申请人：——

  公开号：US9192610B2

  公开（公告）日：2015-11-24
• US9796687B2
  申请人：——

  公开号：US9796687B2

  公开（公告）日：2017-10-24