5-(2-hydroxyphenyl)-3-methyl-1-(2-pyridyl)-1H-pyrazole-4-carboxylic acid methyl ester | 948598-88-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-(2-hydroxyphenyl)-3-methyl-1-(2-pyridyl)-1H-pyrazole-4-carboxylic acid methyl ester
• 英文别名: 5-(2-hydroxybenzoyl)-3-methyl-1-(2-pyridinyl)pyrazol-4-carboxylic acid methyl ester；5-(2-hydroxybenzoyl)-3-methyl-1-(2-pyridin)pyrazol-4-carboxylic acid methyl ester；5-(2-hydroxyphenyl)-3-methyl-1-(2-pyridyl)-1H-pyrazol-4-carboxylic acid methyl ester；Methyl 5-(2-hydroxyphenyl)-3-methyl-1-pyridin-2-ylpyrazole-4-carboxylate
• CAS: 948598-88-7
• 化学式: C₁₇H₁₅N₃O₃
• 分子量: 309.324
• InChiKey: CCYICRAJPLOTOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  77.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(2-hydroxyphenyl)-3-methyl-1-(2-pyridyl)-1H-pyrazole-4-carboxylic acid methyl ester 反应 5.0h， 生成 3-methyl-1-(2-pyridinyl)-1H-chromene[4,3-c]pyrazol-4-one
  参考文献：
  名称：

  具有吡啶-吡唑衍生物的新型Pt（II），Pd（II）和Cu（II）配合物的合成，晶体结构，理论计算和细胞毒性作用

  摘要：

  的合成，结构和细胞毒活性的Pt（II），钯（II）和Cu（II）通式MLCl的络合物2（M =铂，钯，铜）2-4和（CuLCl 2）2 5其中L是吡唑螯合物 配体描述了3-甲基-1-（2-吡啶基）-1H-亚甲基[4，3 - c ]吡唑-4-酮1。配合物的特征在于元素分析，红外线和 1 H NMR光谱以及电喷雾 质谱。还使用以下方法研究了化合物3和5X射线衍射。另外，通过计算获得了几何形状，部分原子电荷和亲脂性，它们决定了它们穿透细胞膜的能力。配合物2–4在金属（II）中心周围呈现正方形平面的几何形状，并采用顺式构型。复杂5是与二聚扭曲的四方锥体在两个铜（配置II）中心，其中通过两个连接μ 2在轴向位置氯桥。检查了这些复合物对HL-60和NALM-6人白血病细胞和黑素瘤WM-115细胞的细胞毒性作用。铂复合顺式- 2对白血病细胞具有中等程度的细胞毒活性，但对黑素瘤细胞具有相对较高的活性，其细胞毒性IC

  DOI：

  10.1039/b808301k

文献信息

• Synthesis and X-ray structure of platinum(II), palladium(II) and copper(II) complexes with pyridine–pyrazole ligands: Influence of ligands’ structure on cytotoxic activity
  作者：Elzbieta Budzisz、Magdalena Miernicka、Ingo-Peter Lorenz、Peter Mayer、Urszula Krajewska、Marek Rozalski

  DOI：10.1016/j.poly.2008.12.013

  日期：2009.2

  -pyrazole-4-phosphonic acid dimethyl ester (2a) has been used to obtain a series of platinum(II), palladium(II) and copper(II) complexes (3a–7a) as potential anticancer compounds. The molecular structures of the platinum(II) and copper(II) complexes 3a and 6a have been determined by X-ray crystallography. The cytotoxicity of the phosphonic ligand 2a and its carboxylic analog 2b as well as their complexes

  新型吡唑配体5-（2-羟基苯基）-3-甲基-1-（2-吡啶基）-1 H-吡唑-4-膦酸二甲酯（2a）已用于获得一系列铂（II） ，钯（II）和铜（II）配合物（3a - 7a）作为潜在的抗癌化合物。铂（II）和铜（II）配合物3a和6a的分子结构已经通过X射线晶体学测定。膦配体2a及其羧酸类似物2b的细胞毒性以及它们的复合物已经在白血病和黑色素瘤细胞系上进行了评估。发现铜（II）配合物比铂（II）或钯（II）配合物在诱导黑色素瘤细胞死亡方面更有效。化合物7b对黑素瘤WM-115细胞的细胞毒性是顺铂的两倍。已经研究了化合物5b与9-甲基鸟嘌呤的反应。
• The cytotoxic effect of Ru(II) complexes with 5-(2-hydroxyphenyl)-3-methyl-1-(2-pyridyl)-1H-pyrazole-4-carboxylic acid methyl ester: Synthesis, X-ray structure and DNA damage potential
  作者：Anna Skoczyńska、Beata Pasternak、Magdalena Małecka、Urszula Krajewska、Marek Mirowski、Anna Merecz-Sadowska、Bolesław T. Karwowski、Joachim Kusz、Elzbieta Budzisz

  DOI：10.1016/j.poly.2019.04.065

  日期：2019.9

  A series of arene ruthenium(II) complexes, 1a-3a, with the general formula [(eta(6)-arene)Ru(L)Cl-2] (where arene = p-cymene, hexamethylbenzene and benzene, respectively, and L = 5-(2-hydroxyphenyl)-3-methyl-1-(2-pyridyl)-1H-pyrazole-4-carboxylic acid methyl ester) were synthesized and characterized by elemental analysis, MS, IR and H-1 NMR spectroscopy. The stability of selected complexes was assessed by UV-Vis spectroscopy over 24 and 48 hour periods. The synthesized complexes were evaluated for in vitro experiments using HL-60, NALM-6, WM-115 and COLO-205, and they showed low cytotoxic activity. The most active compound, 2a, possesses IC50 = 41.17 +/- 3.68 mu M, which is comparable to the reference compound quercetin. X-ray crystallographic analysis of compound 1a found that the ruthenium complex adopts a piano-stool type of geometry, with crystal packing stabilized by a 3-D net of O-H center dot center dot center dot Cl and C-H center dot center dot center dot Cl type hydrogen bonds, the latter forming dimers in the crystal lattice. The most active complexes in the cytotoxicity experiments were selected for evaluation of the damage percentage in NALM-6 cells by a comet assay: the extent of DNA fragmentation in the lymphoblastic leukemia cells indicated that the analyzed ruthenium(II) complexes triggered DNA damage. (C) 2019 Elsevier Ltd. All rights reserved.
• Copper(II) complexes with derivatives of pyrazole as potential antioxidant enzyme mimics
  作者：Bogumiła Kupcewicz、Krzysztof Sobiesiak、Katarzyna Malinowska、Kamila Koprowska、Malgorzata Czyz、Bernhard Keppler、Elżbieta Budzisz

  DOI：10.1007/s00044-012-0233-5

  日期：2013.5

  A series of six mononuclear Cu(II) complexes with pyrazole-based ligands: 5-(2-hydroxybenzoyl)-3-methyl-1-(2-pyridinyl)-1H-pyrazol-4-phosphonic acid dimethyl ester (1a), 5-(2-hydroxyphenyl)-3-methyl-1-(2-pyridylo)-1H-pyrazole-4-carboxylic acid methyl ester (1b) and 1-benzothiazol-2-yl-5-(2-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carboxylic acid methyl ester (1c) were characterized regarding to electrochemical and antioxidant properties. All complexes exhibit suitable Cu(II)/Cu(I) redox potential (E (1/2)) to act as antioxidant enzymes mimic. The five of these complexes were found to be trifunctional enzyme mimics possessing SOD, CAT and GPx-like catalytic activities. Moreover, Cu(II) complexes were capable to decrease ROS level in melanoma cells and observed effects were not merely a reflection of cytotoxicity.
• Synthesis and structure of novel copper(II) complexes with pyrazole derived ligands and metal–ligand interaction in solution
  作者：Aleksander Kufelnicki、Magdalena Woźniczka、Lilianna Chęcińska、Magdalena Miernicka、Elżbieta Budzisz

  DOI：10.1016/j.poly.2006.12.043

  日期：2007.7

  Two new ligands of the coumarin type have been synthesized and characterized by H-1, C-13 NMR, IR and MS. The crystal and molecular structures of ligand 2, determined by the X-ray diffraction method, are presented. With copper(II) these ligands create solid complexes of the type CuLCl2, where L is 5-(2-hydroxybenzoyl)-3-methyl-1-(2-pyridinyl)pyrazol-4-carboxylic acid methyl ester (2) or 3-methyl-1-(2-pyridinyl)-1H-chromene[4,3-c]pyrazol-4-on (3). The new copper(II) complexes have been characterized by elemental analysis and solid state FT-IR. The protonation constants of ligands 2 and 3 have been determined in 5% v/v 1,4-dioxane-water solution (25 degrees C). The coordination modes in the complexes with copper(II) are discussed for 2 on the basis of potentiometric and UV-Vis data. (C) 2007 Elsevier Ltd. All rights reserved.