N,N-dibenzyl-N'-(furan-2-carbonyl)thiourea

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: N,N-dibenzyl-N'-(furan-2-carbonyl)thiourea
• 英文别名: N-(2-furoyl)-N',N'-dibenzylthiourea；N,N-dibenzyl-N'-furoylthiourea；1-furoyl-3,3-dibenzylthiourea；N-(dibenzylcarbamothioyl)furan-2-carboxamide
• 化学式: C₂₀H₁₈N₂O₂S
• 分子量: 350.441
• InChiKey: RIAGJTRLNNOHEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  77.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cobalt(II) diacetate tetrahydrate 、 N,N-dibenzyl-N'-(furan-2-carbonyl)thiourea 在 NaOH 作用下， 以 乙醇 为溶剂， 以80%的产率得到bis(N,N-dibenzyl-N'-furoylthioureato)cobalt(II)
  参考文献：
  名称：

  Synthesis and structural characterization of cobalt(II) and copper(II) complexes with N,N-disubstituted-N′-acylthioureas

  摘要：

  A new complexes of Co(II) and Cu(II) with N,N-disubstituted-N'-acylthioureas have been prepared and characterized by elemental analysis, and spectroscopic techniques. The structure of N,N-diethyl-N'-furoylthiourea and Co(II) complexes with N,N-diethyl-N'-furoyl- and N,N-diethyl-N'-benzoylthiourea were determined by X-ray crystallography. The structural data reveal that the acylthiourea moiety adopts a cis conformation in the crystal and the complexes show a slightly distorted square-planar geometry. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.02.008
• 作为产物：
  描述：

  呋喃甲酰氯 以 丙酮 为溶剂， 生成 N,N-dibenzyl-N'-(furan-2-carbonyl)thiourea
  参考文献：
  名称：

  Synthesis and structural characterization of cobalt(II) and copper(II) complexes with N,N-disubstituted-N′-acylthioureas

  摘要：

  A new complexes of Co(II) and Cu(II) with N,N-disubstituted-N'-acylthioureas have been prepared and characterized by elemental analysis, and spectroscopic techniques. The structure of N,N-diethyl-N'-furoylthiourea and Co(II) complexes with N,N-diethyl-N'-furoyl- and N,N-diethyl-N'-benzoylthiourea were determined by X-ray crystallography. The structural data reveal that the acylthiourea moiety adopts a cis conformation in the crystal and the complexes show a slightly distorted square-planar geometry. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2012.02.008

文献信息

• On the cytotoxic activity of Pd(II) complexes of N,N-disubstituted-N′-acyl thioureas
  作者：Ana M. Plutín、Raúl Mocelo、Anislay Alvarez、Raúl Ramos、Eduardo E. Castellano、Marcia R. Cominetti、Angelica E. Graminha、Antonio G. Ferreira、Alzir A. Batista

  DOI：10.1016/j.jinorgbio.2014.01.022

  日期：2014.5

  Manipulation of the structure of ligands or of complexes represents a strategy for which is possible to modify the potential mechanism of their action against the cancer cells. Here we present the cytotoxicity of some new palladium complexes and our intention is to show the importance of non-coordinated atoms of the ligands in the cytotoxicity of the complexes. New complexes of palladium (II), with general

  合理设计抗癌药物是增加其细胞毒性并最大程度降低其毒性的最有希望的策略之一。操纵配体或复合物的结构代表了一种可能改变其针对癌细胞作用的潜在机制的策略。在这里，我们介绍了一些新的钯配合物的细胞毒性，我们的目的是表明配体的非配位原子在配合物的细胞毒性中的重要性。通式为[Pd（PPh 3）2（L）] PF 6或[PdCl（PPh 3）的钯（II）的新配合物）（L）]，合成了L = N，N-二取代-N'-酰基硫脲，并通过元素分析，摩尔电导率，熔点，IR，NMR（1 H，13 C和31 P 1 H }）光谱学。光谱数据与包含O，S螯合的配体的配合物一致。与复合物的结构Ñ，Ñ二甲基Ñ '-benzoylthiourea，Ñ，Ñ二苯基Ñ '-benzoylthiourea，Ñ，Ñ二乙基Ñ '-furoylthiourea，和Ñ，Ñ二苯基Ñ通过X射线晶体学测定法测定了'-呋喃基硫脲，证实了配体通过硫和氧
• Probing the relationships between molecular conformation and intermolecular contacts in<i>N</i>,<i>N</i>-dibenzyl-<i>N</i>′-(furan-2-carbonyl)thiourea
  作者：Hiram Pérez、Rodrigo S. Corrêa、Ana María Plutín、Beatriz O'Reilly、Marcelo B. Andrade

  DOI：10.1107/s0108270111052620

  日期：2012.1.15

  In the crystal structure of the title compound, C₂₀H₁₈N₂O₂S, molecules are linked by bifurcated C—H...O hydrogen-bond interactions, giving rise to chains whose links are composed of alternating centrosymmetrically disposed pairs of molecules and characterized byR₂²(10) andR₂²(20) hydrogen-bonding motifs. Also, N—H...S hydrogen bonds form infinite zigzag chains along the [010] direction, which exhibit theC(4) motif. Hirshfeld surface and fingerprint plots were used to explore the intermolecular interactions in the crystal structure. This analysis confirms the important role of C—H...O hydrogen bonds in the molecular conformation and in the crystal structure, providing a potentially useful tool for a full understanding of the intermolecular interactions in acylthiourea derivatives.

  在标题化合物 C20H18N2O2S 的晶体结构中，分子通过分叉的 C-H...O氢键相互作用连接在一起，形成了由交替的中心对称排列的分子对组成的链，并具有 R22(10) 和 R22(20) 氢键图案。此外，N-H...S 氢键沿[010]方向形成无限之字链，表现出 C(4) 主题。利用 Hirshfeld 表面和指纹图来探索晶体结构中的分子间相互作用。这项分析证实了 C-H...O 氢键在分子构象和晶体结构中的重要作用，为全面了解酰基硫脲衍生物的分子间相互作用提供了一个潜在的有用工具。
• Ru(II)-based complexes with N-(acyl)-N′,N′-(disubstituted)thiourea ligands: Synthesis, characterization, BSA- and DNA-binding studies of new cytotoxic agents against lung and prostate tumour cells
  作者：Rodrigo S. Correa、Katia M. de Oliveira、Fábio G. Delolo、Anislay Alvarez、Raúl Mocelo、Ana M. Plutin、Marcia R. Cominetti、Eduardo E. Castellano、Alzir A. Batista

  DOI：10.1016/j.jinorgbio.2015.04.008

  日期：2015.9

  Four ruthenium(II)-based complexes with N-(acyl)-N',N'-(disubstituted)thiourea derivatives (Th) were obtained. The compounds, with the general formula trans-[Ru(PPh3)(2)(Th)(bipy)]PF6, interact with bovine serum albumin (BSA) and DNA. BSA-binding constants, which were in the range of 3.3-6.5 x 10(4) M-1, and the thermodynamic parameters (Delta G, Delta H and Delta S), suggest spontaneous interactions with this protein by electrostatic forces due to the positive charge of the complexes. Also, binding constant by spectrophotometric DNA titration (Kb = 0.8-1.8 x 10(4) M-1) and viscosity studies indicate weak interactions between the complexes and DNA. Cytotoxicity assays against DU-145 (prostate cancer) and A549 (lung cancer) tumour cells revealed that the complexes are more active in tumour cells than in normal (L929) cells, and that they present high cytotoxicity (low IC50 values) compared with the reference metallodrug, cisplatin. (C) 2015 Published by Elsevier Inc.