N-(5-bromo-1H-pyrazolo[3,4-b]pyridin-3-yl)butyramide | 405224-25-1

• 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: N-(5-bromo-1H-pyrazolo[3,4-b]pyridin-3-yl)butyramide
• 英文别名: N-(5-bromo-2H-pyrazolo[3,4-b]pyridin-3-yl)butanamide
• CAS: 405224-25-1
• 化学式: C₁₀H₁₁BrN₄O
• 分子量: 283.128
• InChiKey: RKAVEWXYBGMVEK-UHFFFAOYSA-N

物化性质

• 沸点：
  520.8±45.0 °C(predicted)
• 密度：
  1.659±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  70.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(5-bromo-1H-pyrazolo[3,4-b]pyridin-3-yl)butyramide 在 四(三苯基膦)钯 、 palladium bis[bis(diphenylphosphino)ferrocene] dichloride 、 potassium acetate 作用下， 以 乙醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[5-(3-吡啶)-1H-吡唑并[3,4-b]吡啶-3-基]丁酰胺
  参考文献：
  名称：

  5-Aryl-pyrazolo[3,4-b]pyridines: potent inhibitors of glycogen synthase kinase-3 (GSK-3)

  摘要：

  A novel series of pyrazolo[3,4-b]pyridines has been identified that are potent inhibitors of glycogen synthase kinase-3 (GSK-3). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00134-3
• 作为产物：
  描述：

  5-溴-3-氰基-2(1H)-吡啶酮 在 吡啶 、 五氯化磷 、 肼 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 N-(5-bromo-1H-pyrazolo[3,4-b]pyridin-3-yl)butyramide
  参考文献：
  名称：

  A Casein kinase 1/Checkpoint kinase 1 pyrazolo-pyridine protein kinase inhibitor as novel activator of the p53 pathway

  摘要：

  Reactivation of the wild-type p53 pathway is one key goal aimed at developing targeted therapeutics in the cancer research field. Although most p53 protein kinases form 'p53-activating' signals, there are few kinases whose action can contribute to the inhibition of p53, as Casein kinase 1 (CK1) and Checkpoint kinase 1 (CHK1). Here we report on a pyrazolo-pyridine analogue showing activity against both CK1 and CHK1 kinases that lead to p53 pathway stabilisation, thus having pharmacological similarities to the p53-activator Nutlin-3. These data demonstrate the emerging potential utility of multivalent kinase inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.046

文献信息

• Pyrazolopyridines and pyrazolopyridazines as antidabetics
  申请人：——

  公开号：US20040019052A1

  公开（公告）日：2004-01-29

  The present invention includes compound of formula (I), 1 or a derivative thereof, wherein Y is CH or N; R 1 is unsubstituted or substituted alkyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted cycloalkenyl, unsubstituted or substituted aryl, aralkyl wherein the aryl and the alkyl moieties may each independently be unsubstituted or substituted, aralkenyl wherein the aryl, and alkenyl moieties may each independently be unsubstituted or substituted, unsubstituted or substituted heterocyclyl, or heterocyclylalkyl wherein the heterocyclyl and the alkyl moieties may each independently be unsubstituted or substituted; and R 2 is unsubstituted aryl or unsubstituted or substituted or substituted heteroaryl. Additionally the present invention includes a process for preparing such a compound, a pharmaceutical composition containing such a compound, and the use of such a compound in medicine.

  本发明包括式(I)的化合物或其衍生物，其中Y是CH或N；R1是未取代或取代的烷基，未取代或取代的环烷基，未取代或取代的烯基，未取代或取代的环烯基，未取代或取代的芳基，芳基烷基，其中芳基和烷基基团各自可以独立地未取代或取代，芳基烯基，其中芳基和烯基基团各自可以独立地未取代或取代，未取代或取代的杂环基，或杂环基烷基，其中杂环基和烷基基团各自可以独立地未取代或取代；以及R2是未取代的芳基或未取代或取代的杂芳基。此外，本发明还包括制备这种化合物的方法，含有这种化合物的药物组合物，以及这种化合物在医学上的用途。
• [EN] PYRAZOLOPYRIDINE DERIVATIVES<br/>[FR] DERIVES DE PYRAZOLOPYRIDINE
  申请人：GLAXO GROUP LTD

  公开号：WO2003068773A1

  公开（公告）日：2003-08-21

  Certain compounds of formula (I), or a salt thereof, or a solvate thereof, wherein R1, R2, R3 and R4 are as defined in the specification, a procees for the preparation of such compounds, a pharmaceutical composition comprising such compounds and the use of such compounds in medicine. For the treatment of conditions associated with a need for inhibition of GSK-3 such as diabetes, conditions associated with diabetes, chronic neurodegenerative conditions including dementias such as Alzheimer's disease, Parkinson's disease, progressive supranuclear palsy, subacute sclerosing panencephalitic parkinsonism, postencephalitic parkinsonism, pugilistic encephalitis, guam parkinsonism-dementia complex, Picks's disease, corticobasal degeneration, frontotemporal dementia, Huntingdon's disease, AIDS associated dementia, amyotrophic lateral sclerosis, multiple sclerosis and neurotraumatic diseases such as acute stroke, mood disorders such as schizophrenia and bipolar disorders, promotion of functional recovery post stroke, cerebral bleeding (for example, due to solidary cerebral amyloid angiopathy), hair loss, obesity, atherosclerotic cardiovascular disease, hypertension, polycystic ovary syndrome, syndrome X, ischaemia, traumatic brain injury, cancer, leukopenia, Down's syndrome, Lewy body disease, inflammation, and immunodeficiency.
• A Casein kinase 1/Checkpoint kinase 1 pyrazolo-pyridine protein kinase inhibitor as novel activator of the p53 pathway
  作者：Anne-Sophie Huart、Barbara Saxty、Andy Merritt、Marta Nekulova、Stephen Lewis、Yide Huang、Borivoj Vojtesek、Catherine Kettleborough、Ted R. Hupp

  DOI：10.1016/j.bmcl.2013.08.046

  日期：2013.10

  Reactivation of the wild-type p53 pathway is one key goal aimed at developing targeted therapeutics in the cancer research field. Although most p53 protein kinases form 'p53-activating' signals, there are few kinases whose action can contribute to the inhibition of p53, as Casein kinase 1 (CK1) and Checkpoint kinase 1 (CHK1). Here we report on a pyrazolo-pyridine analogue showing activity against both CK1 and CHK1 kinases that lead to p53 pathway stabilisation, thus having pharmacological similarities to the p53-activator Nutlin-3. These data demonstrate the emerging potential utility of multivalent kinase inhibitors. (C) 2013 Elsevier Ltd. All rights reserved.
• 5-Aryl-pyrazolo[3,4-b]pyridines: potent inhibitors of glycogen synthase kinase-3 (GSK-3)
  作者：Jason Witherington、Vincent Bordas、Stephen L Garland、Deirdre M.B Hickey、Robert J Ife、John Liddle、Martin Saunders、David G Smith、Robert W Ward

  DOI：10.1016/s0960-894x(03)00134-3

  日期：2003.5

  A novel series of pyrazolo[3,4-b]pyridines has been identified that are potent inhibitors of glycogen synthase kinase-3 (GSK-3). (C) 2003 Elsevier Science Ltd. All rights reserved.