3-(2-dimethylamino-ethyl)-2-thioxo-2,3-dihydro-1H-quinazolin-4-one | 16951-27-2

• 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-dimethylamino-ethyl)-2-thioxo-2,3-dihydro-1H-quinazolin-4-one
• 英文别名: 3-(2-Dimethylamino-ethyl)-2-thiono-1,2,3,4-tetrahydro-chinazolinon-(4)；3-[2-(dimethylamino)ethyl]-2-thioxo-2,3-dihydroquinazolin-4(1H)-one；3-[2-(dimethylamino)ethyl]-2-sulfanylidene-1H-quinazolin-4-one
• CAS: 16951-27-2
• 化学式: C₁₂H₁₅N₃OS
• mdl: MFCD06358029
• 分子量: 249.337
• InChiKey: GQCRCQLETCLZLO-UHFFFAOYSA-N

物化性质

• 沸点：
  377.0±44.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 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：

  靛红酸酐 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 12.75h， 生成 3-(2-dimethylamino-ethyl)-2-thioxo-2,3-dihydro-1H-quinazolin-4-one
  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

• 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。
• US9868728B2
  申请人：——

  公开号：US9868728B2

  公开（公告）日：2018-01-16
• [EN] QUINAZOLINE DERIVATIVES, COMPOSITIONS, AND USES RELATED THERETO<br/>[FR] DÉRIVÉS QUINAZOLINE, COMPOSITIONS ET UTILISATIONS CORRESPONDANTES
  申请人：UNIV EMORY

  公开号：WO2012058211A2

  公开（公告）日：2012-05-03

  The invention relates to quinazoline derivatives, compositions, and methods related thereto. In certain embodiments, the invention relates to inhibitors of NADPH-oxidase.
• Thioxo-dihydroquinazolin-one Compounds as Novel Inhibitors of Myeloperoxidase
  作者：Yang Li、Thota Ganesh、Becky A. Diebold、Yerun Zhu、James W. McCoy、Susan M. E. Smith、Aiming Sun、J. David Lambeth

  DOI：10.1021/acsmedchemlett.5b00287

  日期：2015.10.8

  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.