3-methoxy-5-nitro-1H-pyrazolo[3,4-b]pyridine | 1186614-21-0

• 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: 3-methoxy-5-nitro-1H-pyrazolo[3,4-b]pyridine
• CAS: 1186614-21-0
• 化学式: C₇H₆N₄O₃
• 分子量: 194.15
• InChiKey: QKCRVRSYXLBOET-UHFFFAOYSA-N

物化性质

• 沸点：
  415.0±40.0 °C(Predicted)
• 密度：
  1.563±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  96.6
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-methoxy-5-nitro-1H-pyrazolo[3,4-b]pyridine 在 palladium 10% on activated carbon 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 16.0h， 以82%的产率得到3-甲氧基-1H-吡唑并[3,4-B]吡啶-5-胺
  参考文献：
  名称：

  [EN] 1H-PYRAZOLO [ 3, 4-B] PYRIDINE COMPOUNDS FOR INHIBITING RAF KINASE
  [FR] COMPOSÉS 1H-PYRAZOLO[3,4-B]PYRIDINES POUR L'INHIBITION DES RAF KINASES

  摘要：

  公式I的化合物对抑制Raf激酶具有用处。本文揭示了利用公式I的化合物及其立体异构体、互变异构体和药用可接受的盐，在哺乳动物细胞中进行体外、体内和体内诊断、预防或治疗这些疾病，或相关的病理条件的方法。【公式I】

  公开号：

  WO2011025968A1
• 作为产物：
  描述：

  5-甲氧基-1H-吡唑-3-胺 、 nitromalondialdehyde sodium salt 以 水 为溶剂， 反应 16.0h， 以43%的产率得到3-methoxy-5-nitro-1H-pyrazolo[3,4-b]pyridine
  参考文献：
  名称：

  [EN] 1H-PYRAZOLO [ 3, 4-B] PYRIDINE COMPOUNDS FOR INHIBITING RAF KINASE
  [FR] COMPOSÉS 1H-PYRAZOLO[3,4-B]PYRIDINES POUR L'INHIBITION DES RAF KINASES

  摘要：

  公式I的化合物对抑制Raf激酶具有用处。本文揭示了利用公式I的化合物及其立体异构体、互变异构体和药用可接受的盐，在哺乳动物细胞中进行体外、体内和体内诊断、预防或治疗这些疾病，或相关的病理条件的方法。【公式I】

  公开号：

  WO2011025968A1

文献信息

• [EN] PYRAZOLE [3, 4-B] PYRIDINE RAF INHIBITORS<br/>[FR] INHIBITEURS DE RAF DE PYRAZOLE[3,4-B]PYRIDINE
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2009111279A1

  公开（公告）日：2009-09-11

  Compounds of Formula I are useful for inhibition of Raf kinases. Methods of using compounds of Formula I and stereoisomers, tautomers, prodrugs and pharmaceutically acceptable salts thereof, for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions are disclosed.

  公式I的化合物对于抑制Raf激酶很有用。本文揭示了利用公式I的化合物及其立体异构体、互变异构体、前药和药学上可接受的盐，在哺乳动物细胞中进行体外、体内和体内诊断、预防或治疗此类疾病或相关病理条件的方法。
• 1H-PYRAZOLO[3,4-B] PYRIDINE COMPOUNDS FOR INHIBITING RAF KINASE
  申请人：Gradl Stefan

  公开号：US20120157452A1

  公开（公告）日：2012-06-21

  Compounds of Formula I are useful for inhibition of Raf kinases. Methods of using compounds of Formula I and stereoisomers, tautomers and pharmaceutically acceptable salts thereof, for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions are disclosed. [FORMULA I]

  式I的化合物对于抑制Raf激酶具有用处。本发明揭示了使用式I化合物及其立体异构体、互变异构体和药学上可接受的盐，在哺乳动物细胞中进行体外、体内和原位诊断、预防或治疗相关病理状况的方法。[式I]
• PYRAZOLE [3, 4-B] PYRIDINE RAF INHIBITORS
  申请人：Ahrendt Kateri A.

  公开号：US20110092479A1

  公开（公告）日：2011-04-21

  Compounds of Formula I are useful for inhibition of Raf kinases. Methods of using compounds of Formula I and stereoisomers, tautomers, prodrugs and pharmaceutically acceptable salts thereof, for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions are disclosed.

  公式I的化合物对于抑制Raf激酶非常有用。本文揭示了使用公式I及其立体异构体、互变异构体、前药和药学上可接受的盐，用于哺乳动物细胞中的体外、原位和体内诊断、预防或治疗相关病理状况的方法。
• Pyrazolopyridine Inhibitors of B-Raf^V600E. Part 1: The Development of Selective, Orally Bioavailable, and Efficacious Inhibitors
  作者：Steve Wenglowsky、Li Ren、Kateri A. Ahrendt、Ellen R. Laird、Ignacio Aliagas、Bruno Alicke、Alex J. Buckmelter、Edna F. Choo、Victoria Dinkel、Bainian Feng、Susan L. Gloor、Stephen E. Gould、Stefan Gross、Janet Gunzner-Toste、Joshua D. Hansen、Georgia Hatzivassiliou、Bonnie Liu、Kim Malesky、Simon Mathieu、Brad Newhouse、Nicholas J. Raddatz、Yingqing Ran、Sumeet Rana、Nikole Randolph、Tyler Risom、Joachim Rudolph、Scott Savage、LeAnn T. Selby、Michael Shrag、Kyung Song、Hillary L. Sturgis、Walter C. Voegtli、Zhaoyang Wen、Brandon S. Willis、Richard D. Woessner、Wen-I Wu、Wendy B. Young、Jonas Grina

  DOI：10.1021/ml200025q

  日期：2011.5.12

  The V600E mutation of B-Raf kinase results in constitutive activation of the MAPK signaling pathway and is present in approximately 7% of all cancers. Using structure-based design, a novel series of pyrazolopyridine inhibitors of B-Raf(V600E) was developed. Optimization led to the identification of 3-methoxy pyrazolopyridines 17 and 19, potent, selective, and orally bioavailable agents that inhibited tumor growth in a mouse xenograft model driven by B-Raf(V600E) with no effect on body weight. On the basis of their in vivo efficacy and preliminary safety profiles, 17 and 19 were selected for further preclinical evaluation.
• Synthesis of 2,6-difluoro-N-(3-[11C]methoxy-1H-pyrazolo[3,4-b]pyridine-5-yl)-3-(propylsulfonamidio)benzamide as a new potential PET agent for imaging of B-RafV600E in cancers
  作者：Min Wang、Mingzhang Gao、Kathy D. Miller、Qi-Huang Zheng

  DOI：10.1016/j.bmcl.2012.12.027

  日期：2013.2

  The authentic standard 2,6-difluoro-N-(3-methoxy-1H-pyrazolo[3,4-b]pyridine-5-yl)-3-(propylsulfonamidio)benzamide was synthesized from 2,6-difluorobenzoic acid and 3-amino-5-hydroxypyrazole in 9 steps with 1% overall chemical yield. Direct desmethylation of the reference standard with TMSCl/NaI gave the precursor 2,6-difluoro-N-(3-hydroxy-1H-pyrazolo[3,4-blpyridine-5-yl)-3-(propylsulfonamidio)benzamide for radiolabeling in 70% yield. The target tracer 2,6-difluoro-N-(3-[C-11]methoxy-1H-pyrazolo[3,4-b]pyridine-5-yl)-3-(propylsulfonamidio)benzamide was prepared from the precursor with [C-11]CH3OTf through O-[C-11]methylation and isolated by HPLC combined with SPE in 40-50% decay corrected radiochemical yields with 370-740 GBq/mu mol specific activity at end of bombardment (EOB). (C) 2012 Elsevier Ltd. All rights reserved.