3-(1-methyl-1H-indol-3-yl)-4-(phenylthio)furan-2,5-dione | 1239912-06-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(1-methyl-1H-indol-3-yl)-4-(phenylthio)furan-2,5-dione
• CAS: 1239912-06-1
• 化学式: C₁₉H₁₃NO₃S
• 分子量: 335.383
• InChiKey: HDVKKPZVOWNJKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  48.3
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-(1-methyl-1H-indol-3-yl)-4-(phenylthio)furan-2,5-dione 在 ammonium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 16³
  参考文献：
  名称：

  Discovery of potent and bioavailable GSK-3β inhibitors

  摘要：

  Here we report on the discovery of a series of maleimides which have high potency and good selectivity for GSK-3 beta. The incorporation of polar groups afforded compounds with good bioavailability. The most potent compound 34 has an IC(50) of 0.6 nM for GSK-3 beta, over 100-fold selectivity against a panel of other kinases, and shows efficacy in rat osteoporosis models. The X-ray structure of GSK-3 beta protein with 34 bound revealed the binding mode of the template and provided insights for future optimization opportunities. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.038
• 作为产物：
  描述：

  苯硫基乙酸 、 1-methylindole-3-glyoxylyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以30%的产率得到3-(1-methyl-1H-indol-3-yl)-4-(phenylthio)furan-2,5-dione
  参考文献：
  名称：

  Discovery of potent and bioavailable GSK-3β inhibitors

  摘要：

  Here we report on the discovery of a series of maleimides which have high potency and good selectivity for GSK-3 beta. The incorporation of polar groups afforded compounds with good bioavailability. The most potent compound 34 has an IC(50) of 0.6 nM for GSK-3 beta, over 100-fold selectivity against a panel of other kinases, and shows efficacy in rat osteoporosis models. The X-ray structure of GSK-3 beta protein with 34 bound revealed the binding mode of the template and provided insights for future optimization opportunities. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.038