2-(1-hydroxy-2-(1H-imidazol-1-yl)ethyl)phenol | 1621686-36-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(1-hydroxy-2-(1H-imidazol-1-yl)ethyl)phenol
• 英文别名: 2-(1-Hydroxy-2-imidazol-1-ylethyl)phenol；2-(1-hydroxy-2-imidazol-1-ylethyl)phenol
• CAS: 1621686-36-9
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 204.228
• InChiKey: LOFVCZOHBCKSSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(1H-imidazol-1-yl)-2'-hydroxyacetophenone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 2-(1-hydroxy-2-(1H-imidazol-1-yl)ethyl)phenol
  参考文献：
  名称：

  Detailed analysis and follow-up studies of a high-throughput screening for indoleamine 2,3-dioxygenase 1 (IDO1) inhibitors

  摘要：

  Indoleamine 2,3-dioxygenase 1 (IDO1) is a key regulator of immune responses and therefore an important therapeutic target for the treatment of diseases that involve pathological immune escape, such as cancer. Here, we describe a robust and sensitive high-throughput screen (HTS) for IDO1 inhibitors using the Prestwick Chemical Library of 1200 FDA-approved drugs and the Maybridge HitFinder Collection of 14,000 small molecules. Of the 60 hits selected for follow-up studies, 14 displayed IC50 values below 20 μM under the secondary assay conditions, and 4 showed an activity in cellular tests. In view of the high attrition rate we used both experimental and computational techniques to identify and to characterize compounds inhibiting IDO1 through unspecific inhibition mechanisms such as chemical reactivity, redox cycling, or aggregation. One specific IDO1 inhibitor scaffold, the imidazole antifungal agents, was chosen for rational structure-based lead optimization, which led to more soluble and smaller compounds with micromolar activity.

  DOI：

  10.1016/j.ejmech.2014.06.078

文献信息

• Detailed analysis and follow-up studies of a high-throughput screening for indoleamine 2,3-dioxygenase 1 (IDO1) inhibitors
  作者：Ute F. Röhrig、Somi Reddy Majjigapu、Marc Chambon、Sylvian Bron、Luc Pilotte、Didier Colau、Benoît J. Van den Eynde、Gerardo Turcatti、Pierre Vogel、Vincent Zoete、Olivier Michielin

  DOI：10.1016/j.ejmech.2014.06.078

  日期：2014.9

  Indoleamine 2,3-dioxygenase 1 (IDO1) is a key regulator of immune responses and therefore an important therapeutic target for the treatment of diseases that involve pathological immune escape, such as cancer. Here, we describe a robust and sensitive high-throughput screen (HTS) for IDO1 inhibitors using the Prestwick Chemical Library of 1200 FDA-approved drugs and the Maybridge HitFinder Collection of 14,000 small molecules. Of the 60 hits selected for follow-up studies, 14 displayed IC50 values below 20 μM under the secondary assay conditions, and 4 showed an activity in cellular tests. In view of the high attrition rate we used both experimental and computational techniques to identify and to characterize compounds inhibiting IDO1 through unspecific inhibition mechanisms such as chemical reactivity, redox cycling, or aggregation. One specific IDO1 inhibitor scaffold, the imidazole antifungal agents, was chosen for rational structure-based lead optimization, which led to more soluble and smaller compounds with micromolar activity.