1-(5-Hydroxymethyl-pyridin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester | 915715-41-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-(5-Hydroxymethyl-pyridin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester
• 英文别名: Ethyl 1-[5-(hydroxymethyl)pyridin-2-yl]pyrazole-4-carboxylate；ethyl 1-[5-(hydroxymethyl)pyridin-2-yl]pyrazole-4-carboxylate
• CAS: 915715-41-2
• 化学式: C₁₂H₁₃N₃O₃
• mdl: MFCD25621113
• 分子量: 247.254
• InChiKey: MODVBTNZGPSNAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  77.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(5-Hydroxymethyl-pyridin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 1-[5-(3-Methyl-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
• 作为产物：
  描述：

  1-(5-Benzyloxymethyl-1-oxy-pyridin-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester 在 palladium dihydroxide 、 环己烯 作用下， 以 乙醇 为溶剂， 反应 0.33h， 以70%的产率得到1-(5-Hydroxymethyl-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

文献信息

• Design and synthesis of a series of novel pyrazolopyridines as HIF 1-α prolyl hydroxylase inhibitors
  作者：Namal C. Warshakoon、Shengde Wu、Angelique Boyer、Richard Kawamoto、Sean Renock、Kevin Xu、Matthew Pokross、Artem G. Evdokimov、Songtao Zhou、Carol Winter、Richard Walter、Marlene Mekel

  DOI：10.1016/j.bmcl.2006.08.017

  日期：2006.11

  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.