6-fluoropyrazolo[1,5-a]pyridine-5-carboxylic acid | 1356145-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡啶类
• 英文名称: 6-fluoropyrazolo[1,5-a]pyridine-5-carboxylic acid
• 英文别名: 6-Fluoropyrazolo[1,5-a]pyridine-5-carboxylic acid
• CAS: 1356145-02-2
• 化学式: C₈H₅FN₂O₂
• 分子量: 180.138
• InChiKey: GKOUATLXUKRJMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-fluoropyrazolo[1,5-a]pyridine-5-carboxylic acid 在 N,N'-羰基二咪唑 、 三氯氧磷 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 6-fluoro-3-formylpyrazolo[1,5-a]pyridine-5-carbonitrile
  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：

  4-(1,3-dioxolan-2-yl)-3-fluoropyridine 在 sodium chlorite 、 sodium dihydrogenphosphate 、 高氯酸 、 硫酸 、 水 、 双氧水 、 2,4-二硝基苯基羟胺 作用下， 以 1,4-二氧六环 、 水 、 丙酮 、 乙腈 为溶剂， 反应 60.0h， 生成 6-fluoropyrazolo[1,5-a]pyridine-5-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

文献信息

• HETEROCYCLIC COMPOUND
  申请人：Fimecs, Inc.

  公开号：EP3831811A1

  公开（公告）日：2021-06-09

  One of the purposes of the present invention is to provide a heterocyclic derivative that has an IAP (particularly XIAP) binding (inhibiting) activity. Another of the purposes of the present invention is to provide a heterocyclic derivative that has an IAP (particularly XIAP) binding (inhibiting) activity and exhibits a protein degradation induction activity. The present invention provides a compound represented by formula (I) (the symbols in the formula are as defined in the present Description) and salts thereof.

  本发明的目的之一是提供一种具有 IAP（特别是 XIAP）结合（抑制）活性的杂环衍生物。本发明的另一个目的是提供一种杂环衍生物，它具有 IAP（特别是 XIAP）结合（抑制）活性并表现出蛋白质降解诱导活性。本发明提供了由式（I）代表的化合物（式中的符号如本说明书中所定义）及其盐类。
• 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.