2-nitro-N-(piperidin-4-ylmethyl)aniline | 1286318-75-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-nitro-N-(piperidin-4-ylmethyl)aniline
• CAS: 1286318-75-9
• 化学式: C₁₂H₁₇N₃O₂
• 分子量: 235.286
• InChiKey: ITELMSSLVQKCSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  69.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-nitro-N-(piperidin-4-ylmethyl)aniline 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 2,4-滴二甲胺盐 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 1-(3,3-dimethyl-2-oxobutyl)-5-(piperidin-4-ylmethyl)-1H-benzo[f][1,3,5]triazepine-2,4(3H,5H)-dione hydrochloride
  参考文献：
  名称：

  Synthesis of a 1,3,5-benzotriazepine-2,4-dione based library

  摘要：

  A library of benzotriazepines has been synthesised employing microwave-mediated synthesis, supported resins and parallel synthesis methodology. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.05.025
• 作为产物：
  描述：

  4-氨甲基哌啶 、 1-氟-2-硝基苯 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-nitro-N-(piperidin-4-ylmethyl)aniline
  参考文献：
  名称：

  Benzimidazole and imidazole inhibitors of histone deacetylases: Synthesis and biological activity

  摘要：

  A series of N-hydroxy-3-[3-(1-substituted-1H-benzoimidazol-2-yl)-phenyl]-acrylamides (5a-5ab) and N-hydroxy-3-[ 3-( 1,4,5-trisubstituted-1H-imidazol-2-yl)-phenyl]-acrylamides (12a-s) were designed, synthesized, and found to be nanomolar inhibitors of human histone deacetylases. Multiple compounds bearing an N1-piperidine demonstrate EC(50)s of 20-100 nM in human A549, HL60, and PC3 cells, in vitro and in vivo hyperacetylation of histones H3 and H4, and induction of p21(waf). Compound 5x displays efficacy in human tumor xenograft models. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.092

文献信息

• Benzimidazole and imidazole inhibitors of histone deacetylases: Synthesis and biological activity
  作者：Jerome C. Bressi、Ron de Jong、Yiqin Wu、Andy J. Jennings、Jason W. Brown、Shawn O’Connell、Leslie W. Tari、Robert J. Skene、Phong Vu、Marc Navre、Xiaodong Cao、Anthony R. Gangloff

  DOI：10.1016/j.bmcl.2010.03.092

  日期：2010.5

  A series of N-hydroxy-3-[3-(1-substituted-1H-benzoimidazol-2-yl)-phenyl]-acrylamides (5a-5ab) and N-hydroxy-3-[ 3-( 1,4,5-trisubstituted-1H-imidazol-2-yl)-phenyl]-acrylamides (12a-s) were designed, synthesized, and found to be nanomolar inhibitors of human histone deacetylases. Multiple compounds bearing an N1-piperidine demonstrate EC(50)s of 20-100 nM in human A549, HL60, and PC3 cells, in vitro and in vivo hyperacetylation of histones H3 and H4, and induction of p21(waf). Compound 5x displays efficacy in human tumor xenograft models. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of a 1,3,5-benzotriazepine-2,4-dione based library
  作者：Irina Chuckowree、Murtaza Ali Syed、Giulia Getti、Asha Parbhu Patel、Hannah Garner、Graham J. Tizzard、Simon J. Coles、John Spencer

  DOI：10.1016/j.tetlet.2012.05.025

  日期：2012.7

  A library of benzotriazepines has been synthesised employing microwave-mediated synthesis, supported resins and parallel synthesis methodology. (C) 2012 Elsevier Ltd. All rights reserved.