N⁶-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-3-nitro-N²-[5-(isopropoxy)-1H-pyrazol-3-yl]pyridine-2,6-diamine | 1079275-30-1

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: N⁶-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-3-nitro-N²-[5-(isopropoxy)-1H-pyrazol-3-yl]pyridine-2,6-diamine
• 英文别名: N6-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-N2-(5-isopropoxy-1H-pyrazol-3-yl)-3-nitropyridine-2,6-diamine；N6-[(1S)-1-(5-Fluoropyridin-2-yl)ethyl]-N2-(5-isopropoxy-1H-pyrazol-3-yl)-3-nitropyridine-2,6-diamine；6-N-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-3-nitro-2-N-(3-propan-2-yloxy-1H-pyrazol-5-yl)pyridine-2,6-diamine
• CAS: 1079275-30-1
• 化学式: C₁₈H₂₀FN₇O₃
• 分子量: 401.4
• InChiKey: GEDVHKAGHJWJLX-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N⁶-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-3-nitro-N²-[5-(isopropoxy)-1H-pyrazol-3-yl]pyridine-2,6-diamine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 N-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-3-(5-isopropoxy-1H-pyrazol-3-yl)-3H-imidazo[4,5-b]pyridin-5-amine
  参考文献：
  名称：

  WO2008/135785

  摘要：

  公开号：
• 作为产物：
  描述：

  2,6-二氯-3-硝基吡啶 在 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 乙腈 、 正丁醇 为溶剂， 反应 28.0h， 生成 N⁶-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-3-nitro-N²-[5-(isopropoxy)-1H-pyrazol-3-yl]pyridine-2,6-diamine
  参考文献：
  名称：

  Discovery of Disubstituted Imidazo[4,5-b]pyridines and Purines as Potent TrkA Inhibitors

  摘要：

  Trk receptor tyrosine kinases have been implicated in cancer and pain. A crystal structure of TrkA with AZ-23 (1a) was obtained, and scaffold hopping resulted in two 5/6-bicyclic series comprising either imidazo[4,5-b]pyridines or purines. Further optimization of these two fusion series led to compounds with subnanomolar potencies against TrkA kinase in cellular assays. Antitumor effects in a TrkA-driven mouse allograft model were demonstrated with compounds 2d and 3a.

  DOI：

  10.1021/ml300074j

文献信息

• Chemical Compounds - 759
  申请人：Astrazeneca AB

  公开号：US20140155394A1

  公开（公告）日：2014-06-05

  The present invention relates to compounds of Formula (I): and to their pharmaceutical compositions, and to their methods of use. These compounds provide a treatment for myeloproliferative disorders and cancer.

  本发明涉及化合物的公式（I）：以及它们的制药组合物和使用方法。这些化合物提供了治疗骨髓增生性疾病和癌症的方法。
• 9-(pyrazol-3-yl)-9H-purine-2-amine and 3-(pyrazol-3-yl) -3H-imidazo[4,5-B] pyridin-5-amine derivatives and their use for the treatment of cancer
  申请人：Davies Audrey

  公开号：US08486966B2

  公开（公告）日：2013-07-16

  The present invention relates to compounds of Formula (I): and to their pharmaceutical compositions, and to their methods of use. These compounds provide a treatment for myeloproliferative disorders and cancer.

  本发明涉及化合物(I)的制备方法，以及它们的制药组合物和使用方法。这些化合物可以用于治疗骨髓增生性疾病和癌症。
• 9-(PYRAZOL-3-YL)-9H-PURINE-2-AMINE AND 3-(PYRAZOL-3-YL) -3H-IMIDAZO[4,5-B] PYRIDIN-5- AMINE DERIVATIVES AND THEIR USE FOR THE TREATMENT OF CANCER
  申请人：Davies Audrey

  公开号：US20100324040A1

  公开（公告）日：2010-12-23

  The present invention relates to compounds of Formula (I): and to their pharmaceutical compositions, and to their methods of use. These compounds provide a treatment for myeloproliferative disorders and cancer.

  本发明涉及式(I)的化合物，以及它们的制药组合物和使用方法。这些化合物提供了治疗骨髓增生性疾病和癌症的方法。
• WO2008/135785
  申请人：——

  公开号：——

  公开（公告）日：——
• Discovery of Disubstituted Imidazo[4,5-<i>b</i>]pyridines and Purines as Potent TrkA Inhibitors
  作者：Tao Wang、Michelle L. Lamb、Michael H. Block、Audrey Molina Davies、Yongxin Han、Ethan Hoffmann、Stephanos Ioannidis、John A. Josey、Zhong-Ying Liu、Paul D. Lyne、Terry MacIntyre、Peter J. Mohr、Charles A. Omer、Tove Sjögren、Kenneth Thress、Bin Wang、Haiyun Wang、Dingwei Yu、Hai-Jun Zhang

  DOI：10.1021/ml300074j

  日期：2012.9.13

  Trk receptor tyrosine kinases have been implicated in cancer and pain. A crystal structure of TrkA with AZ-23 (1a) was obtained, and scaffold hopping resulted in two 5/6-bicyclic series comprising either imidazo[4,5-b]pyridines or purines. Further optimization of these two fusion series led to compounds with subnanomolar potencies against TrkA kinase in cellular assays. Antitumor effects in a TrkA-driven mouse allograft model were demonstrated with compounds 2d and 3a.