4-[(3-tert-butyl-1H-pyrazol-5-yl)amino]-3-nitrobenzoate | 1020210-39-2

• 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: 4-[(3-tert-butyl-1H-pyrazol-5-yl)amino]-3-nitrobenzoate
• 英文别名: methyl 4-[(3-tert-butyl-1H-pyrazol-5-yl)amino]-3-nitrobenzoate；methyl 4-[(5-tert-butyl-1H-pyrazol-3-yl)amino]-3-nitrobenzoate
• CAS: 1020210-39-2；1304789-08-9
• 化学式: C₁₅H₁₈N₄O₄
• 分子量: 318.332
• InChiKey: BGTSSBOZSPVQIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[(3-tert-butyl-1H-pyrazol-5-yl)amino]-3-nitrobenzoate 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 methyl 1-(5-tert-butyl-1H-pyrazol-3-yl)-2-phenyl-1H-benzimidazole-5-carboxylate
  参考文献：
  名称：

  Synthesis of novel 1,2,5-trisubstituted benzimidazoles as potential antitumor agents

  摘要：

  Novel methyl 1-(5-tert-butyl-1H-pyrazol-3-yl)-2-(aryl)-1H-benzo[d]imidazole-5-carboxylates 11 were synthesized by following a four-step strategy involving a nucleophilic aromatic displacement (SNAr) and a solvent free approach as key steps for the formation of the desired products. Structure of intermediates and products were confirmed by X-ray diffraction as well as the tautomeric rearrangement suffered by the pyrazole moiety during the curse of the final cyclization process. Several of the obtained compounds were screened by the US National Cancer Institute (NCI) for their ability to inhibit 60 different human tumor cell lines. Products 11b and 11n exhibited the highest activity against a range of cancer cell lines with remarkable values in panels of Non-Small Cell Lung Cancer, Melanoma and Leukemia, with GI(50) range of 1.15-7.33 mu M and 0.167-7.59 mu M, respectively, and suitable LC50 with values greater than 100 mu M. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.06.006
• 作为产物：
  描述：

  4-氟-3-硝基苯甲酸 在 硫酸 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 生成 4-[(3-tert-butyl-1H-pyrazol-5-yl)amino]-3-nitrobenzoate
  参考文献：
  名称：

  Synthesis of novel 1,2,5-trisubstituted benzimidazoles as potential antitumor agents

  摘要：

  Novel methyl 1-(5-tert-butyl-1H-pyrazol-3-yl)-2-(aryl)-1H-benzo[d]imidazole-5-carboxylates 11 were synthesized by following a four-step strategy involving a nucleophilic aromatic displacement (SNAr) and a solvent free approach as key steps for the formation of the desired products. Structure of intermediates and products were confirmed by X-ray diffraction as well as the tautomeric rearrangement suffered by the pyrazole moiety during the curse of the final cyclization process. Several of the obtained compounds were screened by the US National Cancer Institute (NCI) for their ability to inhibit 60 different human tumor cell lines. Products 11b and 11n exhibited the highest activity against a range of cancer cell lines with remarkable values in panels of Non-Small Cell Lung Cancer, Melanoma and Leukemia, with GI(50) range of 1.15-7.33 mu M and 0.167-7.59 mu M, respectively, and suitable LC50 with values greater than 100 mu M. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.06.006

文献信息

• Solution-Phase and Solid-Phase Synthesis of 1-Pyrazol-3-ylbenzimidazoles
  作者：Jairo Quiroga、Ernesto Mata、Jaime Portilla、Rodrigo Abonía、Braulio Insuasty、Manuel Nogueras、Justo Cobo

  DOI：10.1055/s-2008-1032030

  日期：2008.2

  The facile solution and solid-phase synthesis of 1-pyrazol-3-ylbenzimidazoles from 4-fluoro-3-nitrobenzoate derivatives and 5(3)-amino-3(5)-subtituted-1 H-pyrazoles is reported. The key step is the unexpected nucleophilic aromatic displacement of the activated fluorine by the exocyclic amino group of the pyrazole ring leading to 4-pyrazolylamino-3-nitrobenzoate derivatives, which are easily converted

  报道了从 4-fluoro-3-nitrobenzoate 衍生物和 5(3)-amino-3(5)-submitted-1 H-pyrazoles 轻松溶液和固相合成 1-pyrazol-3-ylbenzimidazoles。关键步骤是活化的氟被吡唑环的环外氨基意外亲核芳族置换，产生 4-吡唑基氨基-3-硝基苯甲酸酯衍生物，这些衍生物很容易在非常高的条件下转化为相应的 1-吡唑-3-基苯并咪唑。孤立的产量。这些新方法对于生成苯并咪唑的各种 1-杂芳基衍生物库非常有用。
• Methyl 4-[(1-acetyl-3-<i>tert</i>-butyl-1<i>H</i>-pyrazol-5-yl)amino]-3-nitrobenzoate
  作者：Edwar Cortés、Rodrigo Abonía、Justo Cobo、Christopher Glidewell

  DOI：10.1107/s0108270110047955

  日期：2011.1.15

  In the molecule of the title compound, C17H20N4O5, there are two intramolecular N-H...O hydrogen bonds having amidic and nitro-group O atoms as the acceptors and together forming a three-centre N-H...(O)(2) system. These interactions appear to play an important role in controlling the relative orientation of the pyrazole and aryl rings. The bond distances provide evidence for some polarization of the electronic structure. Molecules are linked into simple chains by a single C-H...O hydrogen bond.