6-(甲硫基)喹唑啉-2,4-二酮 | 1027428-70-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 6-(甲硫基)喹唑啉-2,4-二酮
• 英文名称: 6-(methylthio)quinazoline-2,4-dione
• 英文别名: 6-methylsulfanyl-1H-quinazoline-2,4-dione
• CAS: 1027428-70-1
• 化学式: C₉H₈N₂O₂S
• 分子量: 208.241
• InChiKey: ZSZUQPJARZIYNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66.24
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-(甲硫基)喹唑啉-2,4-二酮 在 双氧水 、 溶剂黄146 、 N,N-二甲基苯胺 、 三乙胺 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 4-(benzylamino)-2-(imidazol-1-yl)-6-(methylsulfonyl)quinazoline
  参考文献：
  名称：

  Discovery of Potent Cyclic GMP Phosphodiesterase Inhibitors. 2-Pyridyl- and 2-Imidazolylquinazolines Possessing Cyclic GMP Phosphodiesterase and Thromboxane Synthesis Inhibitory Activities

  摘要：

  Moderate cyclic GMP phosphodiesterase (cGMP-PDE, PDE V) inhibitor 2-phenyl-4-anilino-quinazoline (1) was identified utilizing MultiCASE assisted drug design (MCADD) technology. Modification of compound 1 was conducted at the 2-, 4-, and 6-positions of the quinazoline ring for enhancement of cGMP-PDE inhibitory activity. The 6-substituted 2-(imidazol-1-yl)-quinazolines are 1000 times more potent in in vitro PDE V enzyme assay than the well-known inhibitor zaprinast. The 6-substituted derivatives of 2-(3-pyridyl)quinazoline 84 and 2-(imidazol-1-yl)quinazoline 86 exhibited more than 1000-fold selectivity for PDE V over the other four PDE isozymes. In addition, cGMP-PDE inhibitors 64, 65, and 73 were found to have an additional property of thromboxane synthesis inhibitory activity.

  DOI：

  10.1021/jm00018a014
• 作为产物：
  描述：

  potassium cyanate 、 2-amino-5-(methylsulfanyl)benzoic acid 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 18.0h， 以66%的产率得到6-(甲硫基)喹唑啉-2,4-二酮
  参考文献：
  名称：

  Discovery of Potent Cyclic GMP Phosphodiesterase Inhibitors. 2-Pyridyl- and 2-Imidazolylquinazolines Possessing Cyclic GMP Phosphodiesterase and Thromboxane Synthesis Inhibitory Activities

  摘要：

  Moderate cyclic GMP phosphodiesterase (cGMP-PDE, PDE V) inhibitor 2-phenyl-4-anilino-quinazoline (1) was identified utilizing MultiCASE assisted drug design (MCADD) technology. Modification of compound 1 was conducted at the 2-, 4-, and 6-positions of the quinazoline ring for enhancement of cGMP-PDE inhibitory activity. The 6-substituted 2-(imidazol-1-yl)-quinazolines are 1000 times more potent in in vitro PDE V enzyme assay than the well-known inhibitor zaprinast. The 6-substituted derivatives of 2-(3-pyridyl)quinazoline 84 and 2-(imidazol-1-yl)quinazoline 86 exhibited more than 1000-fold selectivity for PDE V over the other four PDE isozymes. In addition, cGMP-PDE inhibitors 64, 65, and 73 were found to have an additional property of thromboxane synthesis inhibitory activity.

  DOI：

  10.1021/jm00018a014

文献信息

• [EN] GLUCOSE UPTAKE INHIBITORS<br/>[FR] INHIBITEURS DE L'ABSORPTION DU GLUCOSE
  申请人：KADMON CORP LLC

  公开号：WO2020005935A1

  公开（公告）日：2020-01-02

  This invention provides compounds that modulate glucose uptake activity and cellular transport/uptake of glucose, and particularly GLUTS3, but also including but not limited to GLUT1-14 (SLC2A1-SLC2A14). Compounds of the invention are useful for treating diseases, including cancer, autoimmune diseases and inflammation, infectious diseases, and metabolic diseases.

  这项发明提供了一种调节葡萄糖摄取活性和细胞对葡萄糖的运输/摄取的化合物，尤其是GLUTS3，但也包括但不限于GLUT1-14（SLC2A1-SLC2A14）。发明中的化合物可用于治疗包括癌症、自身免疫性疾病和炎症、感染性疾病以及代谢性疾病。
• Inhibitors of phosphatases
  申请人：——

  公开号：US20040186116A1

  公开（公告）日：2004-09-23

  The present invention relates to compounds that inhibit phosphatases, compositions thereof, and methods of using those compounds and compositions for treating diseases.

  本发明涉及抑制磷酸酶的化合物、其组成物以及使用这些化合物和组成物治疗疾病的方法。
• INHIBITORS OF PHOSPHATASES
  申请人：Saunders Jeffrey O.

  公开号：US20090060968A1

  公开（公告）日：2009-03-05

  The present invention relates to compounds that inhibit phosphatases, compositions thereof, and methods of using those compounds and compositions for treating diseases.

  本发明涉及抑制磷酸酶的化合物，其组成物和使用这些化合物和组成物治疗疾病的方法。
• US7439249B2
  申请人：——

  公开号：US7439249B2

  公开（公告）日：2008-10-21
• [EN] INHIBITORS OF PHOSPHATASES<br/>[FR] INHIBITEURS DE PHOSPHATASES
  申请人：VERTEX PHARMA

  公开号：WO2004060878A2

  公开（公告）日：2004-07-22

  The present invention relates to compounds that inhibit phosphatases, compositions thereof, and methods of using those compounds and compositions for treating diseases.