2-(1H-imidazol-1-yl)methyl-4H-chromen-4-one | 154774-83-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-(1H-imidazol-1-yl)methyl-4H-chromen-4-one
• 英文别名: 2-(Imidazol-1-ylmethyl)-4-Oxo[4H]-1-Benzopyran；2-(Imidazol-1-ylmethyl)chromen-4-one
• CAS: 154774-83-1
• 化学式: C₁₃H₁₀N₂O₂
• 分子量: 226.235
• InChiKey: PYYAMCXYNZXUHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2'-羟基苯乙酮 在 氢溴酸 、 sodium hydride 作用下， 以 吡啶 、 溶剂黄146 、 乙腈 为溶剂， 反应 12.75h， 生成 2-(1H-imidazol-1-yl)methyl-4H-chromen-4-one
  参考文献：
  名称：

  Exploiting the Chromone Scaffold for the Development of Inhibitors of Corticosteroid Biosynthesis

  摘要：

  The inhibition of corticosteroid biosynthesis could be considered as an emerging strategy to reduce their abnormally high levels, and in this framework CYP11B1 and CYP11B2 represent the most promising targets. In continuing our studies on flavonoid-like scaffolds as privileged structures in medicinal chemistry, in this paper we describe a small library of pyridyl- and imidazolylmethylchromones as potential inhibitors of these enzymes. Testing results proved that position 3 of the chromone scaffold is the most favorable for the introduction of the heme-coordinating heterocycles and, among them, the 4-imidazolyl moiety is the most convenient for the interaction with the heme iron of the selected cytochromes. A low nanomolar inhibitor of CYP11B1 (5c) was obtained) endowed with reasonable selectivity toward CYP11B2 and able to better discriminate with respect to CYP17 and CYP19.

  DOI：

  10.1021/acs.jmedchem.5b01609

文献信息

• Aminoalkylchromones, leurs procédés de préparation et les compositions qui les contiennent
  申请人：ADIR ET COMPAGNIE

  公开号：EP0580503A1

  公开（公告）日：1994-01-26

  L'invention concerne des composés de formule générale (I) : avec R1, R2, R3, R4, R5, R6 et Z définis dans la description, leurs isomères optiques et leurs sels d'addition à un acide ou une base pharmaceutiquement acceptable. Médicaments.

  本发明涉及通式 (I) 的化合物： 中定义的 R1、R2、R3、R4、R5、R6 和 Z 及其光学异构体，以及它们与药学上可接受的酸或碱的加成盐。药物。
• US5519023A
  申请人：——

  公开号：US5519023A

  公开（公告）日：1996-05-21
• Exploiting the Chromone Scaffold for the Development of Inhibitors of Corticosteroid Biosynthesis
  作者：Silvia Gobbi、Qingzhong Hu、Christina Zimmer、Matthias Engel、Federica Belluti、Angela Rampa、Rolf W. Hartmann、Alessandra Bisi

  DOI：10.1021/acs.jmedchem.5b01609

  日期：2016.3.24

  The inhibition of corticosteroid biosynthesis could be considered as an emerging strategy to reduce their abnormally high levels, and in this framework CYP11B1 and CYP11B2 represent the most promising targets. In continuing our studies on flavonoid-like scaffolds as privileged structures in medicinal chemistry, in this paper we describe a small library of pyridyl- and imidazolylmethylchromones as potential inhibitors of these enzymes. Testing results proved that position 3 of the chromone scaffold is the most favorable for the introduction of the heme-coordinating heterocycles and, among them, the 4-imidazolyl moiety is the most convenient for the interaction with the heme iron of the selected cytochromes. A low nanomolar inhibitor of CYP11B1 (5c) was obtained) endowed with reasonable selectivity toward CYP11B2 and able to better discriminate with respect to CYP17 and CYP19.