2,3-bis(3,5-dimethyl-1H-pyrazol-1-yl)cyclohexa-2,5-diene-1,4-dione | 138152-21-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-bis(3,5-dimethyl-1H-pyrazol-1-yl)cyclohexa-2,5-diene-1,4-dione
• 英文别名: 2,3-bis(3,5-dimethylpyrazol-1-yl)-1,4-benzoquinone；2,3-bis(3,5-dimethylpyrazol-1-yl)cyclohexa-2,5-diene-1,4-dione
• CAS: 138152-21-3
• 化学式: C₁₆H₁₆N₄O₂
• 分子量: 296.329
• InChiKey: VNWMFUKDSRALHE-UHFFFAOYSA-N

物化性质

• 沸点：
  311.0±42.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.85
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69.78
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2,3-bis(3,5-dimethyl-1H-pyrazol-1-yl)cyclohexa-2,5-diene-1,4-dione 在 硫酸 、 硝酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 生成 2,3-bis(4-nitro-3,5-dimethylpyrazol-1-yl)-1,4-benzoquinone
  参考文献：
  名称：

  Reaction of pyrazole addition to quinones

  摘要：

  The reactions of pyrazole, 4-nitropyrazole, 3,5-dimethylpyrazole, and 4-chloro-3,5-dimethylpyrazole with 1,4-benzoquinone in dioxane have been analyzed. Mono- and 2,3-bis-adducts were obtained and only in the case of pyrazole was a 2,5-bis(pyrazol-1-yl)-1,4-dihydroxybenzene formed. Further oxidation of the mono- and bis-adducts with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) afforded the quinones, which in turn added 1 mol of azole (pyrazole and imidazole) to yield tetrapyrazolylquinols. Nitration of the 2,3-bis(pyrazol-1-yl)- and 2,3-bis(3,5-dimethylpyrazol-1-yl)-1,4-dihydroxybenzenes has been performed to prepare the corresponding 4-nitropyrazolyl derivatives.

  DOI：

  10.1021/jo00032a048
• 作为产物：
  描述：

  1,4-dihydroxy-2,3-bis(3',5'-dimethylpyrazol-1'-yl)benzene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以85%的产率得到2,3-bis(3,5-dimethyl-1H-pyrazol-1-yl)cyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  Cytotoxicity and reactivity of a redox active 1,4-quinone-pyrazole compound and its Ru(II)-p-cymene complex

  摘要：

  Quinone based compounds display activation in hypoxia, an environment prevalent in tumours. We have synthesized a bis(pyrazole) based 1,4-quinone compound suitable for metal chelation. The quinone (L2) converted to hydroquinone (H(2)L1) during the complex synthesis leading to [Ru-II(eta(6)-p-cym)(H(2)L1)Cl](PF6) (1). We found from 'FINMR studies that in the methanolic solution L2 stoichiometrically converted to H(2)L1 while oxidizing the methanol to formaldehyde. L2 crystallized in monoclinic space group I2/a while complex 1 crystallizes in P2(1)/c. Cyclic voltammetry of the redox non-innocent L2 showed quasi-reversible (Delta Ep = 67 mV) redox behaviour with E-1/2 at 0.12 V w.r.t. NHE. Complex 1 is stable at pH 7.4 in presence of 4 mM chloride and does not hydrolyse even up to 24 h. L2 showed IC50, values of 155 and 123 mu M against metastatic breast adenocarcinoma (MDA-MB231) and pancreatic carcinoma (MIA PaCa-2) respectively. L2 gets activated by ca. 2.7-fold in hypoxia against MIA PaCa-2 cells. The mechanistic studies showed ROS accumulation and oxidation of NADH to NAD(+), which may be responsible for the cytotoxicity. The reactivity studies showed that conversion to hydroquinone by reaction with NADH or glutathione is irreversible. Complex 1 is not cytotoxic up to 100 mu M in normoxia or hypoxia. Complex 1 displays irreversible redox behavior in cyclic voltammetry displaying two overlapping oxidation peaks at 1.00 and 1.57 V w.r.t. NHE, which may be assigned to the conversion of hydroquinone to quinone and Ru-II -> Ru-III respectively.

  DOI：

  10.1016/j.ica.2019.119361
• 作为试剂：
  描述：

  甲醇 在 2,3-bis(3,5-dimethyl-1H-pyrazol-1-yl)cyclohexa-2,5-diene-1,4-dione 作用下， 以 氘代甲醇 为溶剂， 反应 0.25h， 生成 聚合甲醛
  参考文献：
  名称：

  Cytotoxicity and reactivity of a redox active 1,4-quinone-pyrazole compound and its Ru(II)-p-cymene complex

  摘要：

  Quinone based compounds display activation in hypoxia, an environment prevalent in tumours. We have synthesized a bis(pyrazole) based 1,4-quinone compound suitable for metal chelation. The quinone (L2) converted to hydroquinone (H(2)L1) during the complex synthesis leading to [Ru-II(eta(6)-p-cym)(H(2)L1)Cl](PF6) (1). We found from 'FINMR studies that in the methanolic solution L2 stoichiometrically converted to H(2)L1 while oxidizing the methanol to formaldehyde. L2 crystallized in monoclinic space group I2/a while complex 1 crystallizes in P2(1)/c. Cyclic voltammetry of the redox non-innocent L2 showed quasi-reversible (Delta Ep = 67 mV) redox behaviour with E-1/2 at 0.12 V w.r.t. NHE. Complex 1 is stable at pH 7.4 in presence of 4 mM chloride and does not hydrolyse even up to 24 h. L2 showed IC50, values of 155 and 123 mu M against metastatic breast adenocarcinoma (MDA-MB231) and pancreatic carcinoma (MIA PaCa-2) respectively. L2 gets activated by ca. 2.7-fold in hypoxia against MIA PaCa-2 cells. The mechanistic studies showed ROS accumulation and oxidation of NADH to NAD(+), which may be responsible for the cytotoxicity. The reactivity studies showed that conversion to hydroquinone by reaction with NADH or glutathione is irreversible. Complex 1 is not cytotoxic up to 100 mu M in normoxia or hypoxia. Complex 1 displays irreversible redox behavior in cyclic voltammetry displaying two overlapping oxidation peaks at 1.00 and 1.57 V w.r.t. NHE, which may be assigned to the conversion of hydroquinone to quinone and Ru-II -> Ru-III respectively.

  DOI：

  10.1016/j.ica.2019.119361