6-bromopyrazolo[1,5-a]pyridine-3-carbaldehyde | 1356144-44-9

• 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-bromopyrazolo[1,5-a]pyridine-3-carbaldehyde
• 英文别名: 6-Bromopyrazolo[1,5-a]pyridine-3-carbaldehyde
• CAS: 1356144-44-9
• 化学式: C₈H₅BrN₂O
• 分子量: 225.044
• InChiKey: NEKUCJYTPZSTAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 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：
  34.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-bromopyrazolo[1,5-a]pyridine-3-carbaldehyde 在 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 N'-((6-bromopyrazolo[1,5-a]pyridin-3-yl)methylene)-N,2-dimethyl-5-nitrobenzenesulfonohydrazide
  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：

  6-溴吡唑并[1,5-a]吡啶-3-羧酸乙酯 在 硫酸 、 水 、 三氯氧磷 作用下， 反应 20.0h， 生成 6-bromopyrazolo[1,5-a]pyridine-3-carbaldehyde
  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

• [EN] COLONY STIMULATING FACTOR-1 RECEPTOR (CSF-1R) INHIBITORS<br/>[FR] INHIBITEURS DU RÉCEPTEUR DE FACTEUR-1 DE STIMULATION DE COLONIES (CSF-1R)
  申请人：GENZYME CORP

  公开号：WO2017015267A1

  公开（公告）日：2017-01-26

  Compounds of the formulas I and XIII, which are useful as colony stimulating factor-1 receptor inhibitors ("CSF 1R inhibitors").

  I和XIII式化合物，可用作促细胞增殖因子-1受体抑制剂（"CSF 1R抑制剂"）。
• [EN] 6-HETEROARYLOXY BENZIMIDAZOLES AND AZABENZIMIDAZOLES AS JAK2 INHIBITORS<br/>[FR] 6-HÉTÉROARYLOXY BENZIMIDAZOLES ET AZABENZIMIDAZOLES UTILISÉS EN TANT QU'INHIBITEURS DE JAK2
  申请人：AJAX THERAPEUTICS INC

  公开号：WO2022140527A1

  公开（公告）日：2022-06-30

  The present disclosure provides 6-heteroaryloxy benzimidazole and azabenzimidazole compounds and compositions thereof useful for inhibiting JAK2.

  本公开提供6-杂环氧基苯并咪唑和氮杂苯并咪唑化合物及其组合物，用于抑制JAK2。
• Use of Carbonyldiimidazole as an Activator of Formic Acid in Pd2(dba)3-Catalyzed Formylation of Aryl Iodides
  作者：Sukhen Karmakar、Sundar Nandhagopal、ZULELAL DOLAS、Arundutt Silamkoti、Anuradha Gupta、Arvind Mathur

  DOI：10.1055/a-2047-9575

  日期：——

  (CDI)-promoted generation of CO from formic acid has been exploited in a reductive formylation of aryl iodides in the presence of tris(dibenzylideneacetone)dipalladium. The reaction conditions are mild with a broad functional-group tolerance that includes keto, bromo, nitrile, ester, and nitro groups. In the reaction pathway, CDI reacts with formic acid to generate a formyl imidazole that ultimately

  羰基二咪唑 (CDI) 促进甲酸生成 CO 已被用于在三（二亚苄基丙酮）二钯存在下芳基碘化物的还原甲酰化。反应条件温和，具有广泛的官能团耐受性，包括酮基、溴基、腈基、酯基和硝基。在反应途径中，CDI 与甲酸反应生成甲酰咪唑，最终在活化的芳基钯络合物上产生甲酰化过程所需的 CO。
• Colony stimulating factor-1 receptor (CSF-1R) inhibitors
  申请人：Genzyme Corporation

  公开号：US11274108B2

  公开（公告）日：2022-03-15

  Compounds of the formulas which are useful as colony stimulating factor-1 receptor inhibitors (“CSF-1R inhibitors”).

  下列式子的化合物 可用作集落刺激因子-1 受体抑制剂（"CSF-1R 抑制剂"）。
• Ring-opening difluorination of pyrazoloazines
  作者：Hugo Ohki、Masaaki Komatsuda、Hiroki Kondo、Junichiro Yamaguchi

  DOI：10.1016/j.tet.2024.134020

  日期：2024.6

  We have developed a novel ring-opening difluorination process for pyrazoloazines. Utilizing 2.5 equivalents of Selectfluor®, this method enables electrophilic difluorination and subsequent ring-opening of pyrazoloazines, yielding the corresponding difluoroalkylated azines. Additionally, our protocol extends to the decarbonylative difluorination of pyrazoloazines when starting with a formyl group at

  我们开发了一种新型的吡唑并嗪开环二氟化工艺。该方法利用 2.5 当量的 Selectflu®，实现亲电二氟化和随后吡唑并嗪的开环，产生相应的二氟烷基化吖嗪。此外，我们的方案还扩展到以 C3 位甲酰基为起始的吡唑并嗪的脱羰二氟化，证明了该方法的多功能性和广泛适用性。二氟化化学的这一进步为二氟化化合物的合成提供了一条新途径，可能丰富药物化学和材料科学从业者的工具包。