3-[(2-methylthio)phenyl]pyrazole | 149739-35-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-[(2-methylthio)phenyl]pyrazole
• 英文别名: 3(5)-<2'-methylthiophenyl>pyrazole；3-[2(methylsulfanyl)phenyl]pyrazole；5-(2-methylsulfanylphenyl)-1H-pyrazole
• CAS: 149739-35-5
• 化学式: C₁₀H₁₀N₂S
• 分子量: 190.269
• InChiKey: UYHTVFQLXHAAKU-UHFFFAOYSA-N

物化性质

• 沸点：
  391.2±25.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  54
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-[(2-methylthio)phenyl]pyrazole 在 N-氯代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以58%的产率得到3-chloropyrazolo<1,5-b><1,2>benzisothiazole
  参考文献：
  名称：

  Moyroud, Joel; Chene, Alain; Guesnet, Jean-Luc, Heterocycles, 1996, vol. 43, # 1, p. 221 - 228

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(甲基硫代)苯甲酸 在 氯化亚砜 、 硫酸 、 magnesium ethylate 、 一水合肼 、 N,N-二甲基甲酰胺 作用下， 以 乙醚 、 乙醇 、 水 、 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 反应 9.33h， 生成 3-[(2-methylthio)phenyl]pyrazole
  参考文献：
  名称：

  Moyroud, Joel; Chene, Alain; Guesnet, Jean-Luc, Heterocycles, 1996, vol. 43, # 1, p. 221 - 228

  摘要：

  DOI：

文献信息

• Mononuclear and Polynuclear Chain Complexes of a Series of Multinucleating N/S Donor Ligands
  作者：Tanya K. Ronson、Harry Adams、Michael D. Ward

  DOI：10.1002/ejic.200500704

  日期：2005.11

  chelating arms derived from 3-[2-(methylsulfanyl)phenyl]pyrazole linked to central aromatic spacers by methylene units. Complexes with a variety of architectures have been obtained, including simple mononuclear complexes and polynuclear chain complexes. The p-xylyl-spaced ligand L1 forms one-dimensional helical coordination polymers with copper(I) and silver(I) ions. These polymers display interligand

  我们已经制备了一系列五个配体，其潜在的 N,S-双齿螯合臂衍生自 3-[2-(甲基硫烷基)苯基]吡唑，通过亚甲基单元与中心芳族间隔基相连。已经获得了具有多种结构的配合物，包括简单的单核配合物和多核链配合物。对二甲苯基间隔的配体 L1 与铜 (I) 和银 (I) 离子形成一维螺旋配位聚合物。这些聚合物在每个螺旋链中显示出配位间芳族堆积相互作用。间二甲苯基间隔的配体 L2 与铜 (I) 形成配位聚合物，但与较大的银 (I) 离子形成单核配合物，其中中心苯环参与 η1 π 型 Ag…C 与AgI。3、3'-联苯间隔配体 L3 也与银 (I) 和铜 (I) 离子形成一维聚合物，但在这种情况下，一个金属中心和下一个金属中心之间的桥接配体序列遵循锯齿形路径而不是呈螺旋状。1,8-萘基间隔的配体 L4 仅与铜 (I) 和银 (I) 离子形成单核配合物，表明该间隔基不够大，无法强制桥接配位模式。由 2,4
• 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.
• PYRAZOLOPYRIMIDINE COMPOUNDS FOR THE TREATMENT OF CANCER
  申请人：The University of North Carolina At Chapel Hill

  公开号：EP2571361A1

  公开（公告）日：2013-03-27
• [EN] THERAPUETIC USES OF SELECTED PYRAZOLOPYRIMIDINE COMPOUNDS WITH ANTI-MER TYROSINE KINASE ACTIVITY<br/>[FR] UTILISATIONS THÉRAPEUTIQUES DE COMPOSÉS PYRAZOLOPYRIMIDINE SÉLECTIONNÉS PRÉSENTANT UNE ACTIVITÉ ANTI-TYROSINE KINASE MER
  申请人：UNIV NORTH CAROLINA

  公开号：WO2015157125A1

  公开（公告）日：2015-10-15

  Pyrazolopyrimidine compounds, methods of use, and processes for making compounds with anti-Mer tyrosine kinase activity comprising Formula I, II, III, IV, or a pharmaceutically acceptable composition, salt, isotopic analog, or prodrug thereof, are provided. The pyrazolopyrimidine compounds described herein have Mer tyrosine kinase (MerTK) inhibitory activity and are useful as anti-infective agents, immunostimulatory and immunomodulatory agents, anti-cancer agents (including against MerTK -/- tumors and ITD and TKD mutant forms of Acute Myeloid Leukemia (AML)), and as adjunctive agents in combination with chemotherapeutic, radiation or other standard of care for neoplasms.