4-amino-5-((4-methoxyphenoxy)methyl)-4H-1,2,4-triazole-3-thiol | 723332-65-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-amino-5-((4-methoxyphenoxy)methyl)-4H-1,2,4-triazole-3-thiol
• 英文别名: 4-amino-5-[(4-methoxyphenoxy)methyl]-4H-1,2,4-triazole-3-thiol；4-amino-3-[(4-methoxyphenoxy)methyl]-1H-1,2,4-triazole-5-thione
• CAS: 723332-65-8
• 化学式: C₁₀H₁₂N₄O₂S
• mdl: MFCD01416483
• 分子量: 252.297
• InChiKey: KJLSUWJYBZBVIJ-UHFFFAOYSA-N

物化性质

• 溶解度：
  10.85 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-amino-5-((4-methoxyphenoxy)methyl)-4H-1,2,4-triazole-3-thiol 、 2-氯苯甲酸 在 三氯氧磷 作用下， 反应 6.0h， 以74%的产率得到6-(2-chlorophenyl)-3-((4-methoxyphenoxy)methyl)[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole
  参考文献：
  名称：

  Novel Lead Structures for p38 MAP Kinase via FieldScreen Virtual Screening

  摘要：

  p38 MAP kinase has received considerable interest in the pharmaceutical industry and remains a valid and interesting target for the treatment of inflammation. To discover novel p38 inhibitors, we applied the ligand-based virtual screening technique, FieldScreen, to 1.2 million commercially available compounds. Fifty-eight diverse compounds were selected for biological analysis, using molecular field similarity to known inhibitors, while explicitly removing any structure that shared a scaffold with previously reported p38 inhibitors. Of these, 11 (19%) showed >= 20% inhibition of p38 at 10 mu M. We chose to prepare analogues of two distinct chemical series resulting in a potential lead compound with pIC(50) of 6.4. Modeling of SAR using FieldAlign, a ligand alignment protocol, was used to rationalize the SAR of the series of thiadiazole based inhibitors.

  DOI：

  10.1021/jm801399r
• 作为产物：
  描述：

  对甲氧基苯氧乙酸 、 硫代卡巴肼 以62%的产率得到4-amino-5-((4-methoxyphenoxy)methyl)-4H-1,2,4-triazole-3-thiol
  参考文献：
  名称：

  Novel Lead Structures for p38 MAP Kinase via FieldScreen Virtual Screening

  摘要：

  p38 MAP kinase has received considerable interest in the pharmaceutical industry and remains a valid and interesting target for the treatment of inflammation. To discover novel p38 inhibitors, we applied the ligand-based virtual screening technique, FieldScreen, to 1.2 million commercially available compounds. Fifty-eight diverse compounds were selected for biological analysis, using molecular field similarity to known inhibitors, while explicitly removing any structure that shared a scaffold with previously reported p38 inhibitors. Of these, 11 (19%) showed >= 20% inhibition of p38 at 10 mu M. We chose to prepare analogues of two distinct chemical series resulting in a potential lead compound with pIC(50) of 6.4. Modeling of SAR using FieldAlign, a ligand alignment protocol, was used to rationalize the SAR of the series of thiadiazole based inhibitors.

  DOI：

  10.1021/jm801399r

文献信息

• Novel Lead Structures for p38 MAP Kinase via FieldScreen Virtual Screening
  作者：Timothy J. Cheeseright、Melanie Holm、Frank Lehmann、Sabine Luik、Marcia Göttert、James L. Melville、Stefan Laufer

  DOI：10.1021/jm801399r

  日期：2009.7.23

  p38 MAP kinase has received considerable interest in the pharmaceutical industry and remains a valid and interesting target for the treatment of inflammation. To discover novel p38 inhibitors, we applied the ligand-based virtual screening technique, FieldScreen, to 1.2 million commercially available compounds. Fifty-eight diverse compounds were selected for biological analysis, using molecular field similarity to known inhibitors, while explicitly removing any structure that shared a scaffold with previously reported p38 inhibitors. Of these, 11 (19%) showed >= 20% inhibition of p38 at 10 mu M. We chose to prepare analogues of two distinct chemical series resulting in a potential lead compound with pIC(50) of 6.4. Modeling of SAR using FieldAlign, a ligand alignment protocol, was used to rationalize the SAR of the series of thiadiazole based inhibitors.