6-methyl-4-thioxo-4,5-dihydro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one | 1089725-77-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 6-methyl-4-thioxo-4,5-dihydro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one
• 英文别名: 6-methy-4-thioxo-4,5-dihydro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one；6-methyl-4-sulfanylidene-2,5-dihydro-1H-pyrrolo[3,4-c]pyridin-3-one
• CAS: 1089725-77-8
• 化学式: C₈H₈N₂OS
• 分子量: 180.23
• InChiKey: ZDUOMNWPCIQTIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  73.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-甲基呋喃醛 、 6-methyl-4-thioxo-4,5-dihydro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one 在 哌啶 作用下， 以 乙醇 为溶剂， 以31%的产率得到(Z)-6-methyl-1-((5-methylfuran-2-yl)methylene)-4-thioxo-4,5-dihydro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one
  参考文献：
  名称：

  Dihydrofuro[3,4-c]pyridinones as Inhibitors of the Cytolytic Effects of the Pore-Forming Glycoprotein Perforin

  摘要：

  Dihydrofuro[3,4-c]pyridinones are the first class of small molecules reported to inhibit the cytolytic effects of the lymphocyte toxin perforin. A lead structure was identified from a high throughput screen, and a series of analogues were designed and prepared to explore structure-activity relationships around the core bicyclic thioxofuropyridinone and pendant furan ring. This resulted in the identification of a submicromolar inhibitor of the perforin-induced lysis of Jurkat T-lymphoma cells.

  DOI：

  10.1021/jm801063n
• 作为产物：
  描述：

  4-(ethoxymethyl)-6-methyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile 在 硫酸 作用下， 反应 72.0h， 以55%的产率得到6-methyl-4-thioxo-4,5-dihydro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one
  参考文献：
  名称：

  Dihydrofuro[3,4-c]pyridinones as Inhibitors of the Cytolytic Effects of the Pore-Forming Glycoprotein Perforin

  摘要：

  Dihydrofuro[3,4-c]pyridinones are the first class of small molecules reported to inhibit the cytolytic effects of the lymphocyte toxin perforin. A lead structure was identified from a high throughput screen, and a series of analogues were designed and prepared to explore structure-activity relationships around the core bicyclic thioxofuropyridinone and pendant furan ring. This resulted in the identification of a submicromolar inhibitor of the perforin-induced lysis of Jurkat T-lymphoma cells.

  DOI：

  10.1021/jm801063n

文献信息

• Dihydrofuro[3,4<i>-c</i>]pyridinones as Inhibitors of the Cytolytic Effects of the Pore-Forming Glycoprotein Perforin
  作者：Gersande Lena、Joseph A. Trapani、Vivien R. Sutton、Annette Ciccone、Kylie A. Browne、Mark J. Smyth、William A. Denny、Julie A. Spicer

  DOI：10.1021/jm801063n

  日期：2008.12.11

  Dihydrofuro[3,4-c]pyridinones are the first class of small molecules reported to inhibit the cytolytic effects of the lymphocyte toxin perforin. A lead structure was identified from a high throughput screen, and a series of analogues were designed and prepared to explore structure-activity relationships around the core bicyclic thioxofuropyridinone and pendant furan ring. This resulted in the identification of a submicromolar inhibitor of the perforin-induced lysis of Jurkat T-lymphoma cells.