4-甲基吡唑并[1,5-a]吡啶-3-羧酸乙酯 | 55899-17-7

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡啶类
• 中文名称: 4-甲基吡唑并[1,5-a]吡啶-3-羧酸乙酯
• 中文别名: 4-甲基吡唑并[1,5-A]吡啶-3-甲酸乙酯
• 英文名称: ethyl 4-methylpyrazolo[1,5-a]pyridine-3-carboxylate
• 英文别名: 4-methyl-pyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester
• CAS: 55899-17-7
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 204.228
• InChiKey: UWJQYTAMOWJIMY-UHFFFAOYSA-N

物化性质

• 熔点：
  60-61 °C(Solv: ligroine (8032-32-4))
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-甲基吡唑并[1,5-a]吡啶-3-羧酸乙酯 在 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 以91%的产率得到4-methylpyrazolo[1,5-a]pyridine-3-carboxylic acid
  参考文献：
  名称：

  Discovery of pyrazolo[1,5-a]pyridines as p110α-selective PI3 kinase inhibitors

  摘要：

  We have made a novel series of pyrazolo[1,5-a]pyridines as PI3 kinase inhibitors, and demonstrated their selectivity for the p110 alpha isoform over the other Class Ia PI3 kinases. We investigated the SAR around the pyrazolo[1,5-a] pyridine ring system, and found compound 5x to be a particularly potent example (p110 alpha IC50 0.9 nM). This compound inhibits cell proliferation and phosphorylation of Akt/PKB, a downstream marker of PI3 kinase activity, and showed in vivo activity in an HCT-116 human xenograft model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.029
• 作为产物：
  描述：

  3-methyl-N-aminopyridinium mesitylenesulfonate 、 丙炔酸乙酯 以25%的产率得到
  参考文献：
  名称：

  TAMURA Y.; SUMIDA Y.; MIKI Y.; IKEDA M., J. CHEM. SOC. PERKIN TRANS , 1975, PART 1, NO 5, 406-409

  摘要：

  DOI：

文献信息

• Benzimidazolone as potent chymase inhibitor: Modulation of reactive metabolite formation in the hydrophobic (P1) region
  作者：Ho Yin Lo、Peter A. Nemoto、Jin Mi Kim、Ming-Hong Hao、Kevin C. Qian、Neil A. Farrow、Daniel R. Albaugh、Danielle M. Fowler、Richard D. Schneiderman、E. Michael August、Leslie Martin、Melissa Hill-Drzewi、Steven S. Pullen、Hidenori Takahashi、Stéphane De Lombaert

  DOI：10.1016/j.bmcl.2011.05.126

  日期：2011.8

  A new class of chymase inhibitor featuring a benzimidazolone core with an acid side chain and a P-1 hydrophobic moiety is described. Incubation of the lead compound with GSH resulted in the formation of a GSH conjugate on the benzothiophene P-1 moiety. Replacement of the benzothiophene with different heterocyclic systems such as indoles and benzoisothiazole is feasible. Among the P-1 replacements, benzoisothiazole prevents the formation of GSH conjugate and an in silico analysis of oxidative potentials agreed with the experimental outcome. (C) 2011 Elsevier Ltd. All rights reserved.
• Discovery of pyrazolo[1,5-a]pyridines as p110α-selective PI3 kinase inhibitors
  作者：Jackie D. Kendall、Patrick D. O’Connor、Andrew J. Marshall、Raphaël Frédérick、Elaine S. Marshall、Claire L. Lill、Woo-Jeong Lee、Sharada Kolekar、Mindy Chao、Alisha Malik、Shuqiao Yu、Claire Chaussade、Christina Buchanan、Gordon W. Rewcastle、Bruce C. Baguley、Jack U. Flanagan、Stephen M.F. Jamieson、William A. Denny、Peter R. Shepherd

  DOI：10.1016/j.bmc.2011.11.029

  日期：2012.1

  We have made a novel series of pyrazolo[1,5-a]pyridines as PI3 kinase inhibitors, and demonstrated their selectivity for the p110 alpha isoform over the other Class Ia PI3 kinases. We investigated the SAR around the pyrazolo[1,5-a] pyridine ring system, and found compound 5x to be a particularly potent example (p110 alpha IC50 0.9 nM). This compound inhibits cell proliferation and phosphorylation of Akt/PKB, a downstream marker of PI3 kinase activity, and showed in vivo activity in an HCT-116 human xenograft model. (C) 2011 Elsevier Ltd. All rights reserved.
• TAMURA Y.; SUMIDA Y.; MIKI Y.; IKEDA M., J. CHEM. SOC. PERKIN TRANS <JCPK-BH>, 1975, PART 1, NO 5, 406-409
  作者：TAMURA Y.、 SUMIDA Y.、 MIKI Y.、 IKEDA M.

  DOI：——

  日期：——