1-[amino(thioxo)methyl]-5-hydroxy-3-phenyl-1H-pyrazole | 72488-81-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-[amino(thioxo)methyl]-5-hydroxy-3-phenyl-1H-pyrazole
• 英文别名: 5-oxo-3-phenyl-2,5-dihydro-pyrazole-1-carbothioic acid amide；5-Oxo-3-phenyl-2,5-dihydro-pyrazol-1-thiocarbonsaeure-amid；3-oxo-5-phenyl-1H-pyrazole-2-carbothioamide
• CAS: 72488-81-4
• 化学式: C₁₀H₉N₃OS
• 分子量: 219.267
• InChiKey: RKMXVFHMSLMGHU-UHFFFAOYSA-N

物化性质

• 沸点：
  390.0±45.0 °C(Predicted)
• 密度：
  1.423±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  copper(II) choride dihydrate 、 1-[amino(thioxo)methyl]-5-hydroxy-3-phenyl-1H-pyrazole 以 甲醇 、 乙酸乙酯 为溶剂， 以49.6%的产率得到dichlorido(1-[amino(thioxo)methyl]-5-hydroxy-3-phenyl-1H-pyrazole-κN²)copper(II)
  参考文献：
  名称：

  Synthesis, physico-chemical properties and biological analysis of newly obtained copper(II) complexes with pyrazole derivatives

  摘要：

  Three new copper(II) complexes containing two different pyrazole bound ligands (1, 2) have been synthesized and characterized by IR, LSI-MS (liquid secondary ion mass spectrometry) and elemental analysis. H-1 NMR spectra of the organic ligands have been recorded. We describe the influence of these complexes on particular cancer cell lines and DNA structure by MTT-assay [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide], APA (acid phosphatase activity)-assay or CD-spectroscopy and agarose gel electrophoresis methods, together with their physico-chemical properties such as lipophilicity and stability in aqueous solution. The cytotoxic effect on HUVEC (endothelial cells) for the most active complex 4 has been also investigated. Moreover, the ability of these complexes to induce apoptosis in cancer cells has been assessed by using fluorescence microscopy. Our results indicate that dichloridobis(1-[amino(thioxo)methyl]-5-hydroxy-3-phenyl-1H-pyrazole-kappa N2)copper(II) is the most potent complex among the tested complexes. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2014.02.014
• 作为产物：
  描述：

  ethyl (3E)-3-(carbamothioylhydrazinylidene)-3-phenylpropanoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 1-[amino(thioxo)methyl]-5-hydroxy-3-phenyl-1H-pyrazole
  参考文献：
  名称：

  β-酮酰胺和β-酮酯衍生的硫半脲与乙酸锌（II）和乙酸镉（II）的反应：金属，取代基，试剂比和温度对金属诱导的环化的影响

  摘要：

  乙酸锌（II）和乙酸镉（II）在甲醇 在各种实验条件下，使用衍生自β-酮酰胺或β-酮的硫代半氨基唑 酯类（HTSC）。这些反应中的一些反应提供了硫代半氨基甲酸酯配合物[M（TSC）2 ]，其中红外 和 核磁共振谱与N，S-配位相容，但多数可得到络合物[ML 2 ]，其中HL是由以下物质产生的取代的2,5-二氢-5-氧代-1 H-吡唑-1-碳硫酰胺环化HTSC。这些吡唑啉酸酯中的一些和HL中的两种配体 被研究 X射线衍射，并讨论了它们的结构。令人惊讶的是，锌（II）乙酸盐 HTSC的摩尔比为1：1时，通常会生成第三种先前未报道的双去质子化的复合物 配体，[Zn（L-H）]，也是当[ZnL 2 ]和Zn（OAc）2在室温下以1：1摩尔比相互作用时形成的。这些L-H络合物在所有常见情况下均高度不溶溶剂，这阻碍了它们的表征，但表明它们本质上是聚合的。

  DOI：

  10.1039/b401674b

文献信息

• De; Dutt, Journal of the Indian Chemical Society, 1928, vol. 5, p. 463
  作者：De、Dutt

  DOI：——

  日期：——
• Synthesis, physico-chemical properties and biological analysis of newly obtained copper(II) complexes with pyrazole derivatives
  作者：Magdalena Grazul、Emina Besic-Gyenge、Caroline Maake、Michal Ciolkowski、Malgorzata Czyz、Roland K.O. Sigel、Elzbieta Budzisz

  DOI：10.1016/j.jinorgbio.2014.02.014

  日期：2014.6

  Three new copper(II) complexes containing two different pyrazole bound ligands (1, 2) have been synthesized and characterized by IR, LSI-MS (liquid secondary ion mass spectrometry) and elemental analysis. H-1 NMR spectra of the organic ligands have been recorded. We describe the influence of these complexes on particular cancer cell lines and DNA structure by MTT-assay [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide], APA (acid phosphatase activity)-assay or CD-spectroscopy and agarose gel electrophoresis methods, together with their physico-chemical properties such as lipophilicity and stability in aqueous solution. The cytotoxic effect on HUVEC (endothelial cells) for the most active complex 4 has been also investigated. Moreover, the ability of these complexes to induce apoptosis in cancer cells has been assessed by using fluorescence microscopy. Our results indicate that dichloridobis(1-[amino(thioxo)methyl]-5-hydroxy-3-phenyl-1H-pyrazole-kappa N2)copper(II) is the most potent complex among the tested complexes. (C) 2014 Elsevier Inc. All rights reserved.
• Reactions of thiosemicarbazones derived from β-keto amides and β-keto esters with Zn(<scp>ii</scp>) and Cd(<scp>ii</scp>) acetates: influence of metal, substitution, reagent ratio and temperature on metal-induced cyclization
  作者：José S. Casas、María V. Castaño、María S. García-Tasende、Enrique Rodríguez-Castellón、Agustín Sánchez、Luisa M. Sanjuán、José Sordo

  DOI：10.1039/b401674b

  日期：——

  Surprisingly, the reactions of zinc(II) acetate with HTSC in 1 ∶ 1 mol ratio usually gave a third, previously unreported type of complex with a dideprotonated ligand, [Zn(L − H)], which was also formed when [ZnL2] and Zn(OAc)2 interacted at room temperature in 1 ∶ 1 mol ratio. These L − H complexes are highly insoluble in all common solvents, which hinders their characterization but suggests that they are

  乙酸锌（II）和乙酸镉（II）在甲醇 在各种实验条件下，使用衍生自β-酮酰胺或β-酮的硫代半氨基唑 酯类（HTSC）。这些反应中的一些反应提供了硫代半氨基甲酸酯配合物[M（TSC）2 ]，其中红外 和 核磁共振谱与N，S-配位相容，但多数可得到络合物[ML 2 ]，其中HL是由以下物质产生的取代的2,5-二氢-5-氧代-1 H-吡唑-1-碳硫酰胺环化HTSC。这些吡唑啉酸酯中的一些和HL中的两种配体 被研究 X射线衍射，并讨论了它们的结构。令人惊讶的是，锌（II）乙酸盐 HTSC的摩尔比为1：1时，通常会生成第三种先前未报道的双去质子化的复合物 配体，[Zn（L-H）]，也是当[ZnL 2 ]和Zn（OAc）2在室温下以1：1摩尔比相互作用时形成的。这些L-H络合物在所有常见情况下均高度不溶溶剂，这阻碍了它们的表征，但表明它们本质上是聚合的。