methyl (1-benzyl-5-hydroxy-1H-pyrazol-3-yl)acetate | 1217487-94-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (1-benzyl-5-hydroxy-1H-pyrazol-3-yl)acetate
• CAS: 1217487-94-9
• 化学式: C₁₃H₁₄N₂O₃
• 分子量: 246.266
• InChiKey: QBEBDFLQOIPJEO-UHFFFAOYSA-N

物化性质

• 沸点：
  438.1±40.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.35
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  64.35
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (1-benzyl-5-hydroxy-1H-pyrazol-3-yl)acetate 、 原乙酸三乙酯 在 溶剂黄146 作用下， 反应 1.0h， 生成 C₁₇H₂₀N₂O₄
  参考文献：
  名称：

  First in Class, Potent, and Orally Bioavailable NADPH Oxidase Isoform 4 (Nox4) Inhibitors for the Treatment of Idiopathic Pulmonary Fibrosis

  摘要：

  We describe the design, synthesis, and optimization of first-in-class series of inhibitors of NADPH oxidase isoform 4 (Nox4), an enzyme implicated in several pathologies, in particular idiopathic pulmonary fibrosis, a life-threatening and orphan disease. Initially, several moderately potent pyrazolopyridine dione derivatives were found during a high-throughput screening campaign. SA R investigation around the pyrazolopyridine dione core led to the discovery of several double-digit nanomolar inhibitors in cell free assays of reactive oxygen species (ROS) production, showing high potency on Nox4 and Nox1. The compounds have little affinity for Nox2 isoform and are selective for Nox4/1 isoforms. The specificity of these compounds was confirmed in an extensive in vitro pharmacological profile, as well as in a counterscreening assay for potential ROS scavenging. Concomitant benefits are good oral bioavailability and high plasma concentrations in vivo, allowing further clinical trials for the potential treatment of fibrotic diseases, cancers, and cardiovascular and metabolic diseases.

  DOI：

  10.1021/jm100773e
• 作为产物：
  描述：

  1,3-丙酮二羧酸二甲酯 、 苄基肼 生成 methyl (1-benzyl-5-hydroxy-1H-pyrazol-3-yl)acetate
  参考文献：
  名称：

  First in Class, Potent, and Orally Bioavailable NADPH Oxidase Isoform 4 (Nox4) Inhibitors for the Treatment of Idiopathic Pulmonary Fibrosis

  摘要：

  We describe the design, synthesis, and optimization of first-in-class series of inhibitors of NADPH oxidase isoform 4 (Nox4), an enzyme implicated in several pathologies, in particular idiopathic pulmonary fibrosis, a life-threatening and orphan disease. Initially, several moderately potent pyrazolopyridine dione derivatives were found during a high-throughput screening campaign. SA R investigation around the pyrazolopyridine dione core led to the discovery of several double-digit nanomolar inhibitors in cell free assays of reactive oxygen species (ROS) production, showing high potency on Nox4 and Nox1. The compounds have little affinity for Nox2 isoform and are selective for Nox4/1 isoforms. The specificity of these compounds was confirmed in an extensive in vitro pharmacological profile, as well as in a counterscreening assay for potential ROS scavenging. Concomitant benefits are good oral bioavailability and high plasma concentrations in vivo, allowing further clinical trials for the potential treatment of fibrotic diseases, cancers, and cardiovascular and metabolic diseases.

  DOI：

  10.1021/jm100773e

文献信息

• Pyrazolo pyridine derivatives as nadph oxidase inhibitors
  申请人：GENKYO TEX SA

  公开号：EP2166009A1

  公开（公告）日：2010-03-24

  The present invention is related to pyrazolo pyridine derivatives of Formula (I), pharmaceutical composition thereof and to their use for the treatment and/or prophylaxis of disorders or conditions related to Nicotinamide adenine dinucleotide phosphate oxidase (NADPH Oxidase).

  本发明涉及Formula (I)的吡唑吡啶衍生物，以及它们的药物组合物，并用于治疗和/或预防与烟酰胺腺嘌呤二核苷酸磷酸酶（NADPH氧化酶）相关的疾病或症状。
• PYRAZOLO PYRIDINE DERIVATIVES AS NADPH OXIDASE INHIBITORS
  申请人：Page Patrick

  公开号：US20110178082A1

  公开（公告）日：2011-07-21

  The present invention is related to pyrazolo pyridine derivatives of Formula (I), pharmaceutical composition thereof and to their use for the treatment and/or prophylaxis of disorders or conditions related to Nicotinamide adenine dinucleotide phosphate oxidase (NADPH Oxidase).

  本发明涉及式（I）的吡唑吡啶衍生物，以及其制药组合物，以及其用于治疗和/或预防与尼克酰胺腺嘌呤二核苷酸磷酸酸化酶（NADPH氧化酶）相关的疾病或病症的用途。
• Pyrazolo pyridine derivatives as NADPH oxidase inhibitors
  申请人：Page Patrick

  公开号：US08455486B2

  公开（公告）日：2013-06-04

  The present invention is related to pyrazolo pyridine derivatives of Formula (I), pharmaceutical composition thereof and to their use for the treatment and/or prophylaxis of disorders or conditions related to Nicotinamide adenine dinucleotide phosphate oxidase (NADPH Oxidase).

  本发明涉及式（I）的吡唑吡啶衍生物，其制药组合物以及它们用于治疗和/或预防与尼克酰胺腺嘌呤二核苷酸磷酸酸化酶（NADPH氧化酶）相关的疾病或病状的用途。
• US8455486B2
  申请人：——

  公开号：US8455486B2

  公开（公告）日：2013-06-04
• US9006238B2
  申请人：——

  公开号：US9006238B2

  公开（公告）日：2015-04-14