6-甲基-1-(苯基磺酰基)-1H-吲哚-4-醇 | 162935-62-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 6-甲基-1-(苯基磺酰基)-1H-吲哚-4-醇
• 英文名称: 6-methyl-1-(phenylsulfonyl)-1H-indol-4-ol
• 英文别名: 1-(Benzenesulfonyl)-6-methylindol-4-ol
• CAS: 162935-62-8
• 化学式: C₁₅H₁₃NO₃S
• 分子量: 287.339
• InChiKey: KXFUFAJWBZZPAX-UHFFFAOYSA-N

物化性质

• 沸点：
  524.0±42.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  67.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-甲基-1-(苯基磺酰基)-1H-吲哚-4-醇 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.67h， 生成 4-(benzyloxy)-6-methyl-1-(phenylsulfonyl)-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  The First Potent Inhibitor of Mammalian Group X Secreted Phospholipase A₂:  Elucidation of Sites for Enhanced Binding

  摘要：

  Using the X-ray structure of human group X secreted phospholipase A(2) (hGX), we carried out structure-based design of indole-based inhibitors and prepared the compounds using a new synthetic route. The most potent compound inhibited hGX and the mouse orthologue with an IC50 of 75 nM. This compound is the most potent hGX inhibitor reported to date and was also found to inhibit a subset of the other mouse and human sPLA(2)s.

  DOI：

  10.1021/jm060136t
• 作为产物：
  描述：

  1-(苯基磺酰基)吡咯 在 四氯化碳 、 sodium hydroxide 、 正丁基锂 、 三氯化铝 、 对甲苯磺酸 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 12.0h， 生成 6-甲基-1-(苯基磺酰基)-1H-吲哚-4-醇
  参考文献：
  名称：

  The First Potent Inhibitor of Mammalian Group X Secreted Phospholipase A₂:  Elucidation of Sites for Enhanced Binding

  摘要：

  Using the X-ray structure of human group X secreted phospholipase A(2) (hGX), we carried out structure-based design of indole-based inhibitors and prepared the compounds using a new synthetic route. The most potent compound inhibited hGX and the mouse orthologue with an IC50 of 75 nM. This compound is the most potent hGX inhibitor reported to date and was also found to inhibit a subset of the other mouse and human sPLA(2)s.

  DOI：

  10.1021/jm060136t

文献信息

• The First Potent Inhibitor of Mammalian Group X Secreted Phospholipase A₂:  Elucidation of Sites for Enhanced Binding
  作者：Brian P. Smart、Rob C. Oslund、Laura A. Walsh、Michael H. Gelb

  DOI：10.1021/jm060136t

  日期：2006.5.1

  Using the X-ray structure of human group X secreted phospholipase A(2) (hGX), we carried out structure-based design of indole-based inhibitors and prepared the compounds using a new synthetic route. The most potent compound inhibited hGX and the mouse orthologue with an IC50 of 75 nM. This compound is the most potent hGX inhibitor reported to date and was also found to inhibit a subset of the other mouse and human sPLA(2)s.