2-(3,4-Dihydroxyphenyl)-6-[(3-morpholin-4-ylphenyl)methylsulfanyl]-4-oxo-2,3-dihydro-1,3-thiazine-5-carbonitrile | 1314884-53-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 2-(3,4-Dihydroxyphenyl)-6-[(3-morpholin-4-ylphenyl)methylsulfanyl]-4-oxo-2,3-dihydro-1,3-thiazine-5-carbonitrile
• CAS: 1314884-53-1
• 化学式: C₂₂H₂₁N₃O₄S₂
• 分子量: 455.558
• InChiKey: OODKERVAZRMWGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  156
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-(4-吗啉基)苯甲醇 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 二甲基硫 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 6.5h， 生成 2-(3,4-Dihydroxyphenyl)-6-[(3-morpholin-4-ylphenyl)methylsulfanyl]-4-oxo-2,3-dihydro-1,3-thiazine-5-carbonitrile
  参考文献：
  名称：

  Structure–Activity Analysis and Cell-Based Optimization of Human Galactokinase Inhibitors

  摘要：

  Classic galactosemia is a rare human disease associated with the accumulation of a toxic level of galactose-1-phosphate (gal-1P) caused by the inherited deficiency of galactose-1-phosphate uridyltransferase (GALT) activity. To reduce the toxic level of gal-1P in patients, we have identified, via high-throughput screening, over 200 small molecule GALK inhibitors. We selected a 4-oxo-3,4-dihydro-2H-1,3-thiazine-5-carbonitrile scaffold for further structure-activity relationships characterization, lead optimization with regards to potency, and efficacy to reduce gal-1P accumulation in patient cells.

  DOI：

  10.1021/ml200131j

文献信息

• Structure–Activity Analysis and Cell-Based Optimization of Human Galactokinase Inhibitors
  作者：Sina I. Odejinmi、Rafael G. Rascon、Manshu Tang、Hariprasad Vankayalapati、Kent Lai

  DOI：10.1021/ml200131j

  日期：2011.9.8

  Classic galactosemia is a rare human disease associated with the accumulation of a toxic level of galactose-1-phosphate (gal-1P) caused by the inherited deficiency of galactose-1-phosphate uridyltransferase (GALT) activity. To reduce the toxic level of gal-1P in patients, we have identified, via high-throughput screening, over 200 small molecule GALK inhibitors. We selected a 4-oxo-3,4-dihydro-2H-1,3-thiazine-5-carbonitrile scaffold for further structure-activity relationships characterization, lead optimization with regards to potency, and efficacy to reduce gal-1P accumulation in patient cells.