4-(4-nitrophenyl)-1-(4-nitrophenyl)-1H-pyrazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-nitrophenyl)-1-(4-nitrophenyl)-1H-pyrazole
• 英文别名: 1,4-Bis(4-nitrophenyl)pyrazole；1,4-bis(4-nitrophenyl)pyrazole
• 化学式: C₁₅H₁₀N₄O₄
• 分子量: 310.269
• InChiKey: BKGZFZNEZNSXNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole 、 4-(4-nitrophenyl)-1-(4-nitrophenyl)-1H-pyrazole 在 rhodium(II) pivalate 作用下， 以 氯苯 为溶剂， 以89%的产率得到rac-(1R,5R)-8-(4-methylphenylsulfonyl)-2,4-bis(4-nitrophenyl)-7-phenyl-2,6,8-triazabicyclo[3.2.1]octa-3,6-diene
  参考文献：
  名称：

  铑催化脱氮二唑-三唑偶联到氮杂桥结构和咪唑基螯合配体

  摘要：

  1,4,8-Triazaocta-1,3,5,7-tetraenes，由 Rh 2 (Piv) 4催化的吡唑与 1-磺酰基-1,2,3-三唑的脱氮偶联原位生成，顺利形成 2 ,6,8-三氮杂双环[3.2.1]octa-3,6-二烯通过分子内氮杂-Diels-Alder环加成反应。这种多米诺反应与随后的环加合物的热或酸催化重排相结合，提供了直接和灵活地获得N-磺酰化 ( Z )-2-(2-氨基乙烯基)咪唑的途径。

  DOI：

  10.1021/acs.orglett.1c01092
• 作为产物：
  描述：

  2-(4-硝基苯基)丙二醛 在 hydrazine hydrate 、 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 生成 4-(4-nitrophenyl)-1-(4-nitrophenyl)-1H-pyrazole
  参考文献：
  名称：

  Design, synthesis, and biologic evaluation of some novel N-arylpyrazole derivatives as cytotoxic agents

  摘要：

  A novel series of N-arylpyrazole derivatives (5a-5d, 7a-7c) has been designed and synthesized via aromatic substitution reaction of N-nonsubstituted pyrazoles with 4-fluoronitrobenzene in the presence of base. The structures of these compounds were established on the basis of elemental (C, H, and N) and spectral analysis (H-1 NMR, C-13 NMR, HRMS, and FT-IR). All the compounds were tested for their cytotoxic activity in vitro against four human tumor cell lines: carcinoma (Bel-7402), nasopharyngeal carcinoma (KB), immature granulocyte leukemia (HL-60), and gastrocarcinoma (BGC-823) by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. The results showed that most of the obtained compounds exhibited promising cytotoxicity against tested carcinoma cell lines with low IC50 values. The bis-pyrazole derivative 7c, bearing alkoxy group on the 5-position of phenyl ring, was the most effective one. It is inhibition of cell growth of Bel-7402 cells was 1.5-fold higher than that found for cisplatin. And, also mono-pyrazole derivatives 5a and 5b, decorated with trifluoromethyl group on the phenyl ring, displayed better cytotoxicity than that of cisplatin against Bel-7402 cell line.

  DOI：

  10.1007/s00044-013-0552-1

文献信息

• Design, synthesis, and biologic evaluation of some novel N-arylpyrazole derivatives as cytotoxic agents
  作者：Shengjie Xu、Shenghui Li、Yonghe Tang、Jinchao Zhang、Shuxiang Wang、Chuanqi Zhou、Xiaoliu Li

  DOI：10.1007/s00044-013-0552-1

  日期：2013.11

  A novel series of N-arylpyrazole derivatives (5a-5d, 7a-7c) has been designed and synthesized via aromatic substitution reaction of N-nonsubstituted pyrazoles with 4-fluoronitrobenzene in the presence of base. The structures of these compounds were established on the basis of elemental (C, H, and N) and spectral analysis (H-1 NMR, C-13 NMR, HRMS, and FT-IR). All the compounds were tested for their cytotoxic activity in vitro against four human tumor cell lines: carcinoma (Bel-7402), nasopharyngeal carcinoma (KB), immature granulocyte leukemia (HL-60), and gastrocarcinoma (BGC-823) by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. The results showed that most of the obtained compounds exhibited promising cytotoxicity against tested carcinoma cell lines with low IC50 values. The bis-pyrazole derivative 7c, bearing alkoxy group on the 5-position of phenyl ring, was the most effective one. It is inhibition of cell growth of Bel-7402 cells was 1.5-fold higher than that found for cisplatin. And, also mono-pyrazole derivatives 5a and 5b, decorated with trifluoromethyl group on the phenyl ring, displayed better cytotoxicity than that of cisplatin against Bel-7402 cell line.
• Rhodium-Catalyzed Denitrogenative Diazole–Triazole Coupling toward Aza-Bridged Structures and Imidazole-Based Chelating Ligands
  作者：Julia O. Strelnikova、Alexander N. Koronatov、Nikolai V. Rostovskii、Alexander F. Khlebnikov、Olesya V. Khoroshilova、Mariya A. Kryukova、Mikhail S. Novikov

  DOI：10.1021/acs.orglett.1c01092

  日期：2021.6.4

  Rh2(Piv)4-catalyzed denitrogenative coupling of pyrazoles with 1-sulfonyl-1,2,3-triazoles, smoothly form 2,6,8-triazabicyclo[3.2.1]octa-3,6-dienes via intramolecular aza-Diels–Alder cycloaddition. This domino reaction, combined with the subsequent thermal or acid-catalyzed rearrangement of the cycloadducts, provides direct and flexible access to N-sulfonylated (Z)-2-(2-aminovinyl)imidazoles.

  1,4,8-Triazaocta-1,3,5,7-tetraenes，由 Rh 2 (Piv) 4催化的吡唑与 1-磺酰基-1,2,3-三唑的脱氮偶联原位生成，顺利形成 2 ,6,8-三氮杂双环[3.2.1]octa-3,6-二烯通过分子内氮杂-Diels-Alder环加成反应。这种多米诺反应与随后的环加合物的热或酸催化重排相结合，提供了直接和灵活地获得N-磺酰化 ( Z )-2-(2-氨基乙烯基)咪唑的途径。