bis(3,5-diisopropyl-1H-pyrazol-1-yl)ketone | 1210393-74-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: bis(3,5-diisopropyl-1H-pyrazol-1-yl)ketone
• CAS: 1210393-74-0
• 化学式: C₁₉H₃₀N₄O
• 分子量: 330.473
• InChiKey: VXHHJAICIGNTHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.09
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  52.71
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  bis(3,5-diisopropyl-1H-pyrazol-1-yl)ketone 在 cobalt(II) chloride 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 19.0h， 生成
  参考文献：
  名称：

  半块状氮混淆的C蝎子的银（I）和铜（I）配合物

  摘要：

  两个新的空间要求苛刻的含氮氮原子的C蝎形配体，其双（3,5-二异丙基吡唑-1-基）甲基与普通吡唑（H L iPr2）或N-甲苯磺酰基吡唑（Ts L iPr2）已经准备好。配体（x L iPr2）与三氟甲磺酸银AgOTf之间的反应产生了[Ag（x L iPr2）]（OTf）类型的四个新化合物（x = Ts，1a ; x = H，2a）或[Ag（x L iPr2）2 ]（OTf）（x = Ts，1b ; x = H，2b）取决于初始金属：配体比率。同样，与[Cu（CH 3 CN）4 ]（PF 6）的反应产生了[Cu（x L iPr2）（CH 3 CN）]（PF 6）类型的四种新化合物（x = Ts，3a ; x = H，图4a）或[铜（X大号IPR2）2 ]（PF 6）（X = Ts时，图3b ; X = H，图4b）。四种衍生物（1a·丙酮，3a，3b· CH 2的固态结构）Cl 2和4b·

  DOI：

  10.1002/ejic.202000173
• 作为产物：
  描述：

  3,5-二异丙基吡唑 在 三光气 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 bis(3,5-diisopropyl-1H-pyrazol-1-yl)ketone
  参考文献：
  名称：

  半块状氮混淆的C蝎子的银（I）和铜（I）配合物

  摘要：

  两个新的空间要求苛刻的含氮氮原子的C蝎形配体，其双（3,5-二异丙基吡唑-1-基）甲基与普通吡唑（H L iPr2）或N-甲苯磺酰基吡唑（Ts L iPr2）已经准备好。配体（x L iPr2）与三氟甲磺酸银AgOTf之间的反应产生了[Ag（x L iPr2）]（OTf）类型的四个新化合物（x = Ts，1a ; x = H，2a）或[Ag（x L iPr2）2 ]（OTf）（x = Ts，1b ; x = H，2b）取决于初始金属：配体比率。同样，与[Cu（CH 3 CN）4 ]（PF 6）的反应产生了[Cu（x L iPr2）（CH 3 CN）]（PF 6）类型的四种新化合物（x = Ts，3a ; x = H，图4a）或[铜（X大号IPR2）2 ]（PF 6）（X = Ts时，图3b ; X = H，图4b）。四种衍生物（1a·丙酮，3a，3b· CH 2的固态结构）Cl 2和4b·

  DOI：

  10.1002/ejic.202000173

文献信息

• Copper Binding Agents Acting as Copper Ionophores Lead to Caspase Inhibition and Paraptotic Cell Death in Human Cancer Cells
  作者：Saverio Tardito、Irene Bassanetti、Chiara Bignardi、Lisa Elviri、Matteo Tegoni、Claudio Mucchino、Ovidio Bussolati、Renata Franchi-Gazzola、Luciano Marchiò

  DOI：10.1021/ja109413c

  日期：2011.4.27

  We report a quantitative structure activity relationship study of a new class of pyrazole-pyridine copper complexes that establishes a clear correlation between the ability to promote copper accumulation and cytotoxicity. Intracellular metal accumulation is maximized when ligand lipophilicity allows the complex to rapidly cross the membrane. Copper and ligand follow different uptake kinetics and reach different intracellular equilibrium concentrations. These results support a model in which the ligand acts as an ionophore for the metal ion, cycling between intra- and extracellular compartments as dissociated or complexed entities. When treating cancer cells with structurally unrelated disulfiram and pyrazole-pyridine copper complexes, as well as with inorganic copper, the same morphological and molecular changes were reproduced, indicating that copper overload is responsible for the cytotoxic effects. Copper-based treatments drive sensitive cancer cells toward paraptotic cell death, a process hallmarked by endoplasmic reticulum stress and massive vacuolization in the absence of apoptotic features. A lack of caspase activation, as observed in copper-treated dying cells, is a consequence of metal-mediated inhibition of caspase-3. Thus, copper acts simultaneously as an endoplasmic reticulum (ER) stress inducer and a caspase-3 inhibitor, forcing the cell into caspase-independent paraptotic death. The establishment of a mechanism of action common to different copper binding agents provides a rationale for the exploitation of copper toxicity as an anticancer tool.
• Metal-organic chains constructed from pre-organized N2S2 donor ligands
  作者：Marcello Gennari、Irene Bassanetti、Luciano Marchiò

  DOI：10.1016/j.poly.2009.05.073

  日期：2010.1

  Three new N2S2 donor ligands 1,1'-((2-(2-(phenylthio)phenylthio)phenyl)methylene)bis(3,5-R-1H-pyrazole), R = H (L-H), R = Me (L-Me), R = i-Pr (Li-Pr) have been prepared and characterized, These bifunctional ligands incorporate two distinct chelate donor systems, by virtue of the presence of bispyrazole and bis-thioether functions. The preferred conformation of these ligands is such that the N-2 and S-2 donor moieties may be oriented in opposite directions, thus favoring the formation of molecular chains when treated with AgBF4. The X-ray structures of Ag(I) complexes show that, depending on the steric hindrance present on the pyrazole rings, these ligands behave as kappa(4)-SSNN-mu bridging tetradentate (when R = H), or kappa(3)-SNN-mu bridging tridentate (when R = Me, i-Pr). Interestingly, [Ag(L-H)]BF4 crystallizes in the chiral space group P4(1), with the molecular chain that is folded around the 4(1) screw axis. (C) 2009 Elsevier Ltd. All rights reserved.