4,4'-(5-(octyloxy)-1,3-phenylene)bis(3,5-dimethyl-1H-pyrazole) | 945763-08-6

• 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'-(5-(octyloxy)-1,3-phenylene)bis(3,5-dimethyl-1H-pyrazole)
• 英文别名: 4-[3-(3,5-dimethyl-1H-pyrazol-4-yl)-5-octoxyphenyl]-3,5-dimethyl-1H-pyrazole
• CAS: 945763-08-6
• 化学式: C₂₄H₃₄N₄O
• 分子量: 394.56
• InChiKey: VLHAEOVSMADMHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,4'-(5-(octyloxy)-1,3-phenylene)bis(3,5-dimethyl-1H-pyrazole) 、 对氟硝基苯 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以92%的产率得到4,4'-(5-(octyloxy)-1,3-phenylene)-bis(3,5-dimethyl-1-(4-nitrophenyl)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

• Self-assembly of metallomacrocycles with dipyrazole ligands and anion sensing of [Pd₄Fe₂] macrocycle with ferrocene-based dipyrazole ligand
  作者：Liao-Yuan Yao、Zheng-Su Yu、Lin Qin、Yi-Zhi Li、Yu Qin、Shu-Yan Yu

  DOI：10.1039/c2dt32576d

  日期：——

  By employing dipalladium corners [(bpy)2Pd2(NO3)2](NO3)2 or [(phen)2Pd2(NO3)2](NO3)2 (where bpy = 2,2′-bipyridine and phen = 1,10-phenanthroline) to bridge ferrocene-based dipyrazole ligand (L11) and m-phenylene-based dipyrazole ligands (L2–32–3) in aqueous solution, a series of positively-charged [M4L2]4+ metallomacrocycles were obtained. Their structures were characterized by 1H NMR, electrospray ionization mass spectrometry (ESI-MS), elemental analysis, and single crystal X-ray diffraction analysis for 1·4NO3 ([(bpy)Pd]4L112}(NO3)4) and 4·4NO3 ([(phen)Pd]4L222}(NO3)4). In their single crystal structures, NO3− anions are located at the dipalladium corners by C–H⋯O hydrogen bonds. Importantly, the anion-sensing properties of ferrocene functionalized [Pd4Fe2] hetero-metallomacrocycle 1 were investigated in acetonitrile by SWV, CV and NMR analysis, showing promise for Br− sensing.

  通过使用二钯角[(bpy)2Pd2(NO3)2]( )2或[(phen)2Pd2( )2]( )2（其中 bpy = 2,2′-联吡啶，phen = 1、在水溶液中，将二茂铁基二吡唑配体（L11）和间苯二酚基二吡唑配体（L2-32-3）桥接起来，得到了一系列带正电荷的 [M4L2]4+ 金属大环。1-4 ([(bpy)Pd]4L112}( )4) 和 4-4 ([(phen)Pd]4L222}( )4) 通过 1H NMR、电喷雾质谱 (ESI-MS)、元素分析和单晶 X 射线衍射分析对它们的结构进行了表征。在它们的单晶结构中， - 阴离子通过 C-H⋯O 氢键位于二钯角上。重要的是，通过 SWV、CV 和 NMR 分析，研究了二茂铁官能化 [Pd4Fe2] 杂金属环 1 在乙腈中的阴离子传感特性，结果表明它有望用于硼传感。