1-[5-(3-Trifluoromethyl-benzyloxymethyl)-pyridin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester | 915715-50-3

• 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: 1-[5-(3-Trifluoromethyl-benzyloxymethyl)-pyridin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester
• CAS: 915715-50-3
• 化学式: C₂₀H₁₈F₃N₃O₃
• 分子量: 405.376
• InChiKey: AQFDWUVIVDYXAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66.24
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-[5-(3-Trifluoromethyl-benzyloxymethyl)-pyridin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 以80%的产率得到1-[5-(3-Trifluoromethyl-benzyloxymethyl)-pyridin-2-yl]-1H-pyrazole-4-carboxylic acid
  参考文献：
  名称：

  Design and synthesis of a series of novel pyrazolopyridines as HIF 1-α prolyl hydroxylase inhibitors

  摘要：

  Recently resolved X-ray crystal structure of HIF-1 alpha prolyl hydroxylase was used to design and develop a novel series of pyrazolopyridines as potent HIF-1 alpha prolyl hydroxylase inhibitors. The activity of these compounds was determined in a human EGLN-1 assay. Structure-based design aided in optimizing the potency of the initial lead (2, IC50 of 11 mu M) to a potent (11I, 190 nM) EGLN-1 inhibitor. Several of these analogs were potent VEGF inducers in a cell-based assay. These pyrazolopyridines were also effective in stabilizing HIF-1 alpha. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.017
• 作为产物：
  描述：

  2-氯-5-羟甲基吡啶 在 palladium dihydroxide 、 双氧水 、 甲基三氧化铼(VII) 、 sodium hydride 、 caesium carbonate 、 环己烯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.83h， 生成 1-[5-(3-Trifluoromethyl-benzyloxymethyl)-pyridin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Design and synthesis of a series of novel pyrazolopyridines as HIF 1-α prolyl hydroxylase inhibitors

  摘要：

  Recently resolved X-ray crystal structure of HIF-1 alpha prolyl hydroxylase was used to design and develop a novel series of pyrazolopyridines as potent HIF-1 alpha prolyl hydroxylase inhibitors. The activity of these compounds was determined in a human EGLN-1 assay. Structure-based design aided in optimizing the potency of the initial lead (2, IC50 of 11 mu M) to a potent (11I, 190 nM) EGLN-1 inhibitor. Several of these analogs were potent VEGF inducers in a cell-based assay. These pyrazolopyridines were also effective in stabilizing HIF-1 alpha. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.017