(Alphar)-alpha-[2-(5-氟-2-羟基苯基)-2-甲基丙基]-alpha-(三氟甲基)-1H-吡咯并[2,3-c]吡啶-2-乙醇 | 1245526-82-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 中文名称: (Alphar)-alpha-[2-(5-氟-2-羟基苯基)-2-甲基丙基]-alpha-(三氟甲基)-1H-吡咯并[2,3-c]吡啶-2-乙醇
• 英文名称: glucocorticoid
• 英文别名: HY14234；4-fluoro-2-[(R)-4,4,4-trifluoro-3-hydroxy-1,1-dimethyl-3-(1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)butyl]phenol；Glucocorticoid receptor agonist；4-fluoro-2-[(4R)-5,5,5-trifluoro-4-hydroxy-2-methyl-4-(1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-yl]phenol
• CAS: 1245526-82-2
• 化学式: C₂₀H₂₀F₄N₂O₂
• 分子量: 396.385
• InChiKey: JFUAWXPBHXKZGA-IBGZPJMESA-N

物化性质

• 沸点：
  563.1±50.0 °C(Predicted)
• 密度：
  1.373
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  69.1
• 氢给体数：
  3
• 氢受体数：
  7

制备方法与用途

生物活性

Glucocorticoid receptor agonist 是 Glucocorticoid 受体激动剂。

反应信息

• 作为产物：
  描述：

  (R)-1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methyl-2-(1H-pyrrolo[2,3-c]pyridin-2-ylmethyl)pentan-2-ol 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到(Alphar)-alpha-[2-(5-氟-2-羟基苯基)-2-甲基丙基]-alpha-(三氟甲基)-1H-吡咯并[2,3-c]吡啶-2-乙醇
  参考文献：
  名称：

  Nonsteroidal Dissociated Glucocorticoid Agonists Containing Azaindoles as Steroid A-Ring Mimetics

  摘要：

  Syntheses and structure activity relationships (SA R) of nonsteroidal glucocorticoid receptor (GR) agonists are described. These compounds contain azaindole moieties as A-ring mimetics and display various degrees of in vitro dissociation between gene transrepression and transactivation. Collagen induced arthritis studies in mouse have demonstrated that in vitro dissociated compounds (R)-16 and (R)-37 have steroid-like anti-inflammatory properties with improved metabolic side effect profiles, such as a reduced increase in body fat and scrum insulin levels, compared to steroids.

  DOI：

  10.1021/jm100751q

文献信息

• SELECTIVE GLUCOCORTICOID RECEPTOR MODIFIERS FOR TREATING IMPAIRED SKIN WOUND HEALING
  申请人：AKRIBES BIOMEDICAL GMBH

  公开号：US20220047602A1

  公开（公告）日：2022-02-17

  The present invention relates to a Selective Glucocorticoid Receptor Modulator (SEGRM), or a pharmaceutically acceptable salt thereof, for use in the treatment of impaired skin wound healing in a subject, an in vitro method for identifying a subject suffering from impaired skin wound healing to be responsive to the treatment with a Selective Glucocorticoid Receptor Modulator (SEGRM), or a pharmaceutically acceptable salt thereof, and kits and kits-of-part related thereto.
• [EN] SELECTIVE GLUCOCORTICOID RECEPTOR MODIFIERS FOR TREATING IMPAIRED SKIN WOUND HEALING<br/>[FR] MODIFICATEURS SÉLECTIFS DU RÉCEPTEUR DE GLUCOCORTICOÏDES POUR LE TRAITEMENT DE LA MAUVAISE CICATRISATION DE PLAIES CUTANÉES
  申请人：AKRIBES BIOMEDICAL GMBH

  公开号：WO2020152193A1

  公开（公告）日：2020-07-30

  The present invention relates to a Selective Glucocorticoid Receptor Modulator (SEGRM), or a pharmaceutically acceptable salt thereof, for use in the treatment of impaired skin wound healing in a subject, an in vitro method for identifying a subject suffering from impaired skin wound healing to be responsive to the treatment with a Selective Glucocorticoid Receptor Modulator (SEGRM), or a pharmaceutically acceptable salt thereof, and kits and kits-of-part related thereto.
• Nonsteroidal Dissociated Glucocorticoid Agonists Containing Azaindoles as Steroid A-Ring Mimetics
  作者：Doris Riether、Christian Harcken、Hossein Razavi、Daniel Kuzmich、Thomas Gilmore、Jörg Bentzien、Edward J. Pack、Donald Souza、Richard M. Nelson、Alison Kukulka、Tazmeen N. Fadra、Ljiljana Zuvela-Jelaska、Josephine Pelletier、Roger Dinallo、Mark Panzenbeck、Carol Torcellini、Gerald H. Nabozny、David S. Thomson

  DOI：10.1021/jm100751q

  日期：2010.9.23

  Syntheses and structure activity relationships (SA R) of nonsteroidal glucocorticoid receptor (GR) agonists are described. These compounds contain azaindole moieties as A-ring mimetics and display various degrees of in vitro dissociation between gene transrepression and transactivation. Collagen induced arthritis studies in mouse have demonstrated that in vitro dissociated compounds (R)-16 and (R)-37 have steroid-like anti-inflammatory properties with improved metabolic side effect profiles, such as a reduced increase in body fat and scrum insulin levels, compared to steroids.