4-oxo-3-(2-(piperidin-1-yl)ethyl)-2-thioxo-1,2,3,4-tetrahydroquinazoline | 717864-94-3

• 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: 4-oxo-3-(2-(piperidin-1-yl)ethyl)-2-thioxo-1,2,3,4-tetrahydroquinazoline
• 英文别名: 3-(2-(piperidin-1-yl)ethyl)-2-thioxo-2,3-dihydroquinazolin-4(1H)-one；3-[2-(Piperidin-1-YL)ethyl]-2-sulfanylidene-1,2,3,4-tetrahydroquinazolin-4-one；3-(2-piperidin-1-ylethyl)-2-sulfanylidene-1H-quinazolin-4-one
• CAS: 717864-94-3
• 化学式: C₁₅H₁₉N₃OS
• 分子量: 289.401
• InChiKey: IMZTYDPFGJUJEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  67.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二硫化碳 、 2-Amino-N-(2-(piperidin-1-yl)ethyl)benzamide 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 4-oxo-3-(2-(piperidin-1-yl)ethyl)-2-thioxo-1,2,3,4-tetrahydroquinazoline
  参考文献：
  名称：

  Thioxo-dihydroquinazolin-one Compounds as Novel Inhibitors of Myeloperoxidase

  摘要：

  Myeloperoxidase (MPO) is a key antimicrobial enzyme, playing a normal role in host defense, but also contributing to inflammatory conditions including neuroinflammatory diseases such as Parkinson's and Alzheimer's. We synthesized and characterized more than 50 quinazolin-4(1H)-one derivatives and showed that this class of compounds inhibits MPO with IC50 values as low as 100 nM. Representative compounds showed partially reversible inhibition that was competitive with respect to Amplex Red substrate and did not result in the accumulation of MPO Compound II. Members of this group show promise for therapeutic development for the treatment of diseases in which inflammation plays a pathogenic role.

  DOI：

  10.1021/acsmedchemlett.5b00287

文献信息

• A Convenient and Efficient Synthesis of 2-Thioxoquinazolinone Derivatives via Microwave Irradiation
  作者：Weiwei Liu、Qiang Zhang、Feng Gong、Zhiling Cao、Yunfeng Huo

  DOI：10.1002/jhet.2036

  日期：2015.3

  The synthesis of 2‐thioxoquinazolinone derivatives was achieved by condensation of isatoic anhydride, primary amine, and carbon disulfide under microwave irradiation. This convenient and efficient method affords the desired products with good to excellent yields. Satisfactory infrared spectroscopy, 1H NMR, and high‐resolution mass spectrometry (electrospray ionization) spectra were obtained for all

  在微波辐射下，通过等规酸酐，伯胺和二硫化碳的缩合反应，可以合成2-硫代氧杂喹唑啉酮衍生物。这种方便而有效的方法可提供所需的产品，并具有良好或极好的收率。对于上述所有化合物，均获得了令人满意的红外光谱，1 H NMR和高分辨率质谱（电喷雾电离）光谱。
• Nanomagnetically modified polyphosphoric acid (NiFe2O4@SiO2–PPA): an efficient, fast, and reusable catalyst for the synthesis of 2-thioxoquinazolinones under solvent-free conditions
  作者：Hossein Eshghi、Amir Khojastehnezhad、Farid Moeinpour、Mehdi Bakavoli、Nafiseh Zeinabi、Sadegh Allameh

  DOI：10.1007/s11164-014-1866-4

  日期：2015.10

  Polyphosphoric acid functionalized silica-coated magnetic nanoparticles with core–shell structure (NiFe2O4@SiO2–PPA) has been used as a magnetically recyclable green catalyst for the one-pot three-component synthesis of 2-thioxoquinazolinones by the reaction of isatoic anhydride, primary amines and thiourea under neat conditions. The catalyst is readily recovered by simple magnetic decantation and can be recycled five times with no significant loss of catalytic activity.

  将具有核壳结构的聚磷酸官能化二氧化硅包覆磁性纳米粒子（NiFe2O4@SiO2-PPA）作为一种磁性可回收绿色催化剂，用于在纯净条件下通过异酸酐、伯胺和硫脲反应一锅三组分合成 2-硫酮喹唑啉酮。通过简单的磁性倾析，催化剂很容易回收，而且可以循环使用五次，催化活性不会明显降低。
• QUINAZOLINE DERIVATIVES, COMPOSITIONS, AND USES RELATED THERETO
  申请人：Lambeth John David

  公开号：US20130225612A1

  公开（公告）日：2013-08-29

  The invention relates to quinazoline derivatives, compositions, and methods related thereto. In certain embodiments, the invention relates to inhibitors of NADPH-oxidase.

  本发明涉及喹唑啉衍生物、组合物及其相关方法。在某些实施例中，本发明涉及NADPH-氧化酶抑制剂。
• Quinazoline derivatives, compositions and uses related thereto
  申请人：Emory University

  公开号：EP2886120A1

  公开（公告）日：2015-06-24

  The invention relates to quinazoline derivatives, compositions, and methods related thereto. In certain embodiments, the invention relates to inhibitors of NADPH-oxidase.

  本发明涉及喹唑啉衍生物、组合物及其相关方法。在某些实施方案中，本发明涉及 NADPH-oxidase 的抑制剂。
• 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.