6-(benzylsulfanyl)-2-(3,4-dihydroxyphenyl)-4-oxo-3,4-dihydro-2H-1,3-thiazine-5-carbonitrile | 892234-24-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 6-(benzylsulfanyl)-2-(3,4-dihydroxyphenyl)-4-oxo-3,4-dihydro-2H-1,3-thiazine-5-carbonitrile
• 英文别名: 6-benzylsulfanyl-2-(3,4-dihydroxyphenyl)-4-oxo-2,3-dihydro-1,3-thiazine-5-carbonitrile
• CAS: 892234-24-1
• 化学式: C₁₈H₁₄N₂O₃S₂
• 分子量: 370.453
• InChiKey: VTROMDPBGYYNKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  144
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-(benzylsulfanyl)-2-(3,4-dihydroxyphenyl)-4-oxo-3,4-dihydro-2H-1,3-thiazine-5-carbonitrile 、 乙酸酐 以 吡啶 为溶剂， 以22%的产率得到[2-Acetyloxy-4-(6-benzylsulfanyl-5-cyano-4-oxo-2,3-dihydro-1,3-thiazin-2-yl)phenyl] acetate
  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
• 作为产物：
  描述：

  3-Benzylsulfanyl-2-cyano-3-sulfanylprop-2-enamide 、 3,4-二羟基苯甲醛 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以61%的产率得到6-(benzylsulfanyl)-2-(3,4-dihydroxyphenyl)-4-oxo-3,4-dihydro-2H-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.