1-methyl-4-nitro-3-(pyridin-2-yl)-1H-pyrazole | 364387-01-9

• 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: 1-methyl-4-nitro-3-(pyridin-2-yl)-1H-pyrazole
• 英文别名: pyridine-2-(1-methyl-4-nitro-1H-pyrazol-3-yl)；2-(1-Methyl-4-nitropyrazol-3-yl)pyridine；2-(1-methyl-4-nitropyrazol-3-yl)pyridine
• CAS: 364387-01-9
• 化学式: C₉H₈N₄O₂
• 分子量: 204.188
• InChiKey: CNXYIDYPCJSIIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  76.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-methyl-4-nitro-3-(pyridin-2-yl)-1H-pyrazole 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以75%的产率得到4-amino-1-methyl-3-(pyridin-2-yl)-1H-pyrazole
  参考文献：
  名称：

  Design and synthesis of novel 3,4-disubstituted pyrazoles for nanomedicine applications against malignant gliomas

  摘要：

  A series of novel 3,4-disubstituted pyrazoles were synthesized. The cytotoxicity against U87MG glioma cell line have been investigated in vitro and three of these compounds showed promising inhibitory activity on cell growth with an IC(50) lower than 90 mu M. AutoDock molecular docking into type I TGF-beta receptor (TGF-beta-RI; PDB: 1py5) has been done for lead optimization of the mentioned compounds as potential TGF-beta-RI1 inhibitors. In particular, 3-aryl-4-amido pyrazole containing long omega-amino-aliphatic chain emerged as a good candidate for further optimization. Entrapment into targetable PEG-based micelles improved growth inhibition IC(50) values up to 100 nM and this could lead to a novel drug delivery strategy for treating glioblastoma. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.01.014
• 作为产物：
  描述：

  2-(1-甲基-1H-吡唑-3-基)吡啶 在 硫酸 、 硝酸 作用下， 反应 49.0h， 以42%的产率得到1-methyl-4-nitro-3-(pyridin-2-yl)-1H-pyrazole
  参考文献：
  名称：

  Design and synthesis of novel 3,4-disubstituted pyrazoles for nanomedicine applications against malignant gliomas

  摘要：

  A series of novel 3,4-disubstituted pyrazoles were synthesized. The cytotoxicity against U87MG glioma cell line have been investigated in vitro and three of these compounds showed promising inhibitory activity on cell growth with an IC(50) lower than 90 mu M. AutoDock molecular docking into type I TGF-beta receptor (TGF-beta-RI; PDB: 1py5) has been done for lead optimization of the mentioned compounds as potential TGF-beta-RI1 inhibitors. In particular, 3-aryl-4-amido pyrazole containing long omega-amino-aliphatic chain emerged as a good candidate for further optimization. Entrapment into targetable PEG-based micelles improved growth inhibition IC(50) values up to 100 nM and this could lead to a novel drug delivery strategy for treating glioblastoma. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.01.014

文献信息

• Synthesis and characterisation of polymeric metal-ion carboxylates from benzene-1,3,5-tricarboxylic acid with Mn(II), Co(II) or Zn(II) and 2,2-bipyridyl, phenanthroline or a pyridyl-2-(1-methyl-1H-pyrazol-3-yl) derivative
  作者：M.John Plater、Mark R.St J. Foreman、R.Alan Howie、Janet M.S. Skakle、Eugenio Coronado、Carlos J. Gómez-Garcı́a、Thomas Gelbrich、Michael B. Hursthouse

  DOI：10.1016/s0020-1693(01)00449-2

  日期：2001.7

  of 13 new co-ordination solids have been prepared of composition [Co(HBTC)(PHEN)(H2O)] (12), [Mn3(BTC)2(PHEN)3] (13), [Mn(HBTC)(6)(H2O)] (14), [Mn(HBTC)(7)(H2O)] (15), [Zn3(BTC)2(6)3(H2O)3]·4H2O (16), [Zn(HBTC)(6)(H2O)] (17), [Zn(H2BTC)2(6)] (18), [Zn(HBTC)(7)(H2O)] (19), [Zn(HBTC)(8)(H2O)] (20), [Zn2(HBTC)2(9)2]·2H2O (21), [Zn(HBTC)(10)(H2O)]·H2O (22), [Co(HBTC)(10)(H2O)]·H2O (23) and [Co(HBTC)(11)(H2O)]

  总共制备了13种新的配位固体，其组成为[Co（HBTC）（PHEN）（H 2 O）]（12），[Mn 3（BTC）2（PHEN）3 ]（13），[Mn （HBTC）（6）（H 2 O）]（14），[Mn（HBTC）（7）（H 2 O）]（15），[Zn 3（BTC）2（6）3（H 2 O）3 ]·4H 2 O（16），[Zn（HBTC）（6）（H 2 O）]（17），[Zn（H2 BTC）2（6）]（18），[Zn（HBTC）（7）（H 2 O）]（19），[Zn（HBTC）（8）（H 2 O）]（20），[Zn 2（HBTC）2（9）2 ]·2H 2 O（21），[Zn（HBTC）（10）（H 2 O）]·H 2 O（22），[Co（HBTC）（10）（H）2 O）]·H 2 O（23）和[Co（HBTC）（11）（H 2 O）]（24）（6 =吡啶-2-（1-甲基-1H-吡唑-3-基）;
• [EN] PYRAZOLE AMIDE COMPOUNDS AS IRAK INHIBITORS<br/>[FR] COMPOSÉS PYRAZOLE AMIDE EN TANT QU'INHIBITEURS D'IRAK
  申请人：RIGEL PHARMACEUTICALS INC

  公开号：WO2018081294A1

  公开（公告）日：2018-05-03

  Disclosed embodiments concern novel interleukin receptor associated kinases (IRAK) inhibitors of formula 1 and compositions comprising such inhibitors. Also disclosed are methods of making and using the compounds and compositions. The disclosed compounds and/ or compositions may be used to treat or prevent an IRAK-associated disease or condition.
• Design and synthesis of novel 3,4-disubstituted pyrazoles for nanomedicine applications against malignant gliomas
  作者：Mauro Comes Franchini、Bianca Flavia Bonini、Carlo Maurizio Camaggi、Denis Gentili、Annalisa Pession、Monica Rani、Elena Strocchi

  DOI：10.1016/j.ejmech.2010.01.014

  日期：2010.5

  A series of novel 3,4-disubstituted pyrazoles were synthesized. The cytotoxicity against U87MG glioma cell line have been investigated in vitro and three of these compounds showed promising inhibitory activity on cell growth with an IC(50) lower than 90 mu M. AutoDock molecular docking into type I TGF-beta receptor (TGF-beta-RI; PDB: 1py5) has been done for lead optimization of the mentioned compounds as potential TGF-beta-RI1 inhibitors. In particular, 3-aryl-4-amido pyrazole containing long omega-amino-aliphatic chain emerged as a good candidate for further optimization. Entrapment into targetable PEG-based micelles improved growth inhibition IC(50) values up to 100 nM and this could lead to a novel drug delivery strategy for treating glioblastoma. (C) 2010 Elsevier Masson SAS. All rights reserved.