2-(N-Phenyl-N-methyl-thiocarbamoylthio)acetic Acid | 20069-27-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(N-Phenyl-N-methyl-thiocarbamoylthio)acetic Acid
• 英文别名: carboxymethyl N-methyl-N-phenyl dithiocarbamate；carboxymethyl N-methyl-N-phenyldithiocarbamate；(methyl-phenyl-thiocarbamoylsulfanyl)-acetic acid；Methyl-phenyl-dithiocarbamidsaeure-carboxymethylester；(Methyl-phenyl-thiocarbamoylmercapto)-essigsaeure；(Methyl-phenyl-thiocarbaminyl)-thioglykolsaeure；carboxymethyl-N-methyl-N-phenyldithiocarbamate；2-[methyl(phenyl)carbamothioyl]sulfanylacetic acid
• CAS: 20069-27-6
• 化学式: C₁₀H₁₁NO₂S₂
• 分子量: 241.335
• InChiKey: MVNDXIQHQVIAAQ-UHFFFAOYSA-N

物化性质

• 熔点：
  197-198 °C (decomp)
• 沸点：
  388.5±44.0 °C(Predicted)
• 密度：
  1.386±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  97.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(N-Phenyl-N-methyl-thiocarbamoylthio)acetic Acid 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 di-pyridyl ketone 4-methyl-4-phenylthiosemicarbazone
  参考文献：
  名称：

  Novel Second-Generation Di-2-Pyridylketone Thiosemicarbazones Show Synergism with Standard Chemotherapeutics and Demonstrate Potent Activity against Lung Cancer Xenografts after Oral and Intravenous Administration in Vivo

  摘要：

  We developed a series of second-generation di-2-pyridyl ketone thiosemicarbazone (DpT) and 2-benzoylpyridine thiosemicarbazone (BpT) ligands to improve the efficacy safety profile of these potential antitumor agents. Two novel DpT analogues, Dp4e4mT and DpC, exhibited pronounced and selective activity against human lung cancer xenografts in vivo via the intravenous and oral routes. Importantly, these analogues did not induce the cardiotoxicity observed at high nonoptimal doses of the first-generation DpT analogue, Dp44mT. The Cu(II) complexes of these ligands exhibited potent antiproliferative activity having redox potentials in a range accessible to biological reductants. The activity of the copper complexes of Dp4e4mT and DpC against lung cancer cells was synergistic in combination with gemcitabine or cisplatin. It was demonstrated by EPR spectroscopy that dimeric copper compounds of the type [CuLCl](2), identified crystallographically, dissociate in solution to give monomeric 1:1 Cu:ligand complexes. These monomers represent the biologically active form of the complex.

  DOI：

  10.1021/jm300768u
• 作为产物：
  描述：

  N-甲基苯胺 在 sodium hydroxide 作用下， 反应 21.0h， 生成 2-(N-Phenyl-N-methyl-thiocarbamoylthio)acetic Acid
  参考文献：
  名称：

  2-Pyridineformamide N(4)-ring incorporated thiosemicarbazones inhibit MCF-7 cells by inhibiting JNK pathway

  摘要：

  In an effort to develop a more potent anticancer therapeutic agent, a series of 2-pyridineformamide thiosemi-carbazones (R = H, 4-CH3, 5-F, 6-CH3 and[GRAPHICS]) have been synthesized and evaluated for their anti-cancer activities against the cancer cells MCF-7 (breast cancer cell line), A-431 and A375 (epidermoid carcinoma cell line), and HeLa (cervical cancer cell line) using MTT assay. All these 2-pyridineformamide thiosemicarbazones exhibited anti-proliferative activities towards these cell lines. 5FAmPyrr possess most profound effects against MCF-7 cells with IC50 of 0.9 mu M. In flow cytometry using Propidium Iodide, 5FAmPyrr was found to induce cell death significantly in a dose dependent manner (100 nM-3 mu M) and inhibited colony formation of MCF-7 cells. This compound induced pro-apoptotic protein Box and inhibited anti apoptotic protein Bcl-2 as well as both c-Jun and Jun N-terminal kinase (abbreviated as JNK) in concentration dependent manner. Further pro-caspase 3 and PARP were inhibited by 5FAmPyrr at concentration of 3 mu M. The results suggest that 5FAmPyrr exhibit anticancer potency and induced cell death by inhibiting MAPK signaling and inducing intrinsic apoptotic pathway. All these indicate that 2-pyridineformamide thiosemicarbazones could be developed as future therapeutics agents to treat cancer.[GRAPHICS].

  DOI：

  10.1016/j.bmcl.2019.04.031

文献信息

• In vitro and in vivo antitumor activity of platinum(II) complexes with thiosemicarbazones derived from 2-formyl and 2-acetyl pyridine and containing ring incorporated at N(4)-position: Synthesis, spectroscopic study and crystal structure of platinum(II) complexes with thiosemicarbazones, potential anticancer agents
  作者：Dimitra Kovala-Demertzi、Athanassios Papageorgiou、Leuteris Papathanasis、Alexandros Alexandratos、Panagiotis Dalezis、John R. Miller、Mavroudis A. Demertzis

  DOI：10.1016/j.ejmech.2008.08.007

  日期：2009.3

  2-acetyl pyridine and containing an azepane ring (hexamethyleneiminyl ring) incorporated at N(4)-position, HL1 (1) and HL2 (2) with platinum(II) afforded the complexes, [Pt(L1)Cl] (3) and [Pt(L2)Cl] (4). Characterization of the compounds was accomplished by means of elemental analysis and spectroscopic techniques NMR, UV–vis and IR spectroscopy. The single-crystal X-ray structure of complex [Pt(L2)Cl] (4)

  2-甲酰基和2-乙酰基吡啶并在N（4）-位处并入HL 1（1）和HL 2（2）的氮杂环戊烷环（六亚甲基亚甲基环）与铂（II）的硫半脲反应，得到配合物， [Pt（L 1）Cl]（3）和[Pt（L 2）Cl]（4）。化合物的表征通过元素分析和光谱技术NMR，UV-vis和IR光谱法完成。配合物[Pt（L 2）Cl]（4）的单晶X射线结构表明，配体单阴离子在与金属过孔的平面构型中进行配位吡啶基N原子，亚胺基N原子和硫醇基S原子。化合物1 - 4已经评估了抗增殖活性体外抗三种人癌细胞系：MCF-7（人乳腺癌细胞系），T24（膀胱癌细胞系），A-549（非小细胞肺癌）和小鼠L-929（从菌株L克隆的成纤维细胞样细胞系）。配体2表现出对所有四种癌细胞系的抗癌活性，而配体1表现出对MCF-7和L-929细胞系的选择性，而复合物4表现出对A-549和T-24癌细胞系的抗性。另外，还对携带白血病P388的小
• Synthesis and Characterization Studies of Cobalt(II), Nickel(II), Copper(II) and Zinc(II) Complexes of Carboxymethyl-N-Methyl-N-Phenyl Dithiocarbamate
  作者：Lekshmi V. Kumar、G. Rathika Nath

  DOI：10.13005/ojc/340649

  日期：2018.12.28

  Complexes of carboxymethyl-N-methyl-N-phenyl dithiocarbamate (DTC) with cobalt(II), nickel((II), copper(II) and zinc(II) complexes were synthesized in 1:2 molar ratio with general formula [M(DTC)2],M=Co(II)/Ni(II)/Cu(II)/Zn(II)} and characterized by elemental analysis, molar conductance, infrared and electronic spectra. The ligand structure was confirmed by 1H and 13C nuclear magnetic resonance spectrum

  进行热分析以确定金属配合物的热稳定性。通过粉末XRD测量，确定了晶格参数，空间群和晶粒尺寸。扫描电子显微镜图像揭示了金属络合物的表面形态。
• Synthesis, characterization and biological studies of cobalt(II), nickel(II), copper(II) and zinc(II) complexes of vanillin-4-methyl-4-phenyl-3-thiosemicarbazone
  作者：Lekshmi V Kumar、G Rathika Nath

  DOI：10.1007/s12039-019-1658-x

  日期：2019.8

  Antimicrobial studies were carried out against gram-positive, gram-negative bacteria and two fungal pathogens. Graphic abstractVanillin-4-methyl-4-phenyl-3-thiosemicarbazone and its cobalt(II), nickel(II), copper(II) and zinc(II) complexes were synthesized and characterized and suitable geometry was proposed. All complexes except copper complex were stable up to 280 °C. The ligand and complexes belong to

  摘要合成了香兰素-4-甲基-4-苯基-3-硫代氨基脲与钴（II），镍（II），铜（II）和锌（II）金属离子的配合物，并通过元素分析，摩尔电导，磁性力矩，红外光谱，电子光谱，1 H和1313 C NMR，质谱和热分析。低摩尔电导值表明所有络合物均为非电解质。光谱研究表明，配体以三齿方式通过硫，氧和氮原子与金属离子配合作用。基于磁矩测量，光谱研究和热分析，提出了适合金属配合物的几何形状。在热重分析的基础上确定配合物的热稳定性，并通过粉末XRD测量来确定配体和配合物的晶格参数，空间群和晶粒尺寸。用SEM分析了配体和配合物的表面形态。对革兰氏阳性，革兰氏阴性细菌和两种真菌病原体进行了抗菌研究。 图形摘要合成并表征了香兰素-4-甲基-4-苯基-3-硫代半脲及其钴（II），镍（II），铜（II）和锌（II）配合物，并提出了合适的几何构型。除铜络合物外，所有络合物在280°C的温度下均稳定。配体和配合
• Imaging Intracellular Zinc by Using a Glyoxal Bis(4‐methyl‐4‐phenyl‐3‐thiosemicarbazone) Ligand
  作者：Duraippandi Palanimuthu、Sridevi Vijay Shinde、Disha Dayal、Kumaravel Somasundaram、Ashoka G. Samuelson

  DOI：10.1002/ejic.201300324

  日期：2013.7.2

  The ligand glyoxal bis(4-methyl-4-phenyl-3-thiosemicarbazone) (GTSCH2) is shown to be a selective fluorescence turn-on sensor for zinc ions (Zn2+). This sensor is easy to synthesize, exhibits excellent sensitivity and selectivity towards Zn2+ over other physiologically relevant cations, and has sub-nanomolar binding affinity. It displays maximum fluorescence response to Zn2+ when the metal/ligand ratio

  配体乙二醛双(4-甲基-4-苯基-3-氨基硫脲) (GTSCH2) 显示为锌离子 (Zn2+) 的选择性荧光开启传感器。该传感器易于合成，与其他生理相关阳离子相比，对 Zn2+ 表现出优异的灵敏度和选择性，并且具有亚纳摩尔的结合亲和力。当金属/配体比为 1:1 时，它对 Zn2+ 显示出最大的荧光响应，并在很宽的 pH 范围内显示出稳定的荧光。通过使用流式细胞术和共聚焦荧光显微镜，在 MCF-7 细胞（人乳腺癌细胞系）中证明了 GTSCH2 对细胞内 Zn2+ 成像的潜力。细胞活力研究表明，该探针具有生物相容性，适用于细胞应用。
• The Copper Reduction Potential Determines the Reductive Cytotoxicity: Relevance to the Design of Metal–Organic Antitumor Drugs
  作者：Elena K. Beloglazkina、Anna A. Moiseeva、Sergey A. Tsymbal、Dmitry A. Guk、Mikhail A. Kuzmin、Olga O. Krasnovskaya、Roman S. Borisov、Elena S. Barskaya、Victor A. Tafeenko、Victoria M. Alpatova、Andrei V. Zaitsev、Alexander V. Finko、Valentina A. Ol’shevskaya、Alexander A. Shtil

  DOI：10.3390/molecules29051032

  日期：——

  the spatial structure of the organic ligand. For cell sensitization to the copper–organic complex, the electrochemical potential of the metal reduction should be lower than the oxidation potential of the reducing agent. Generally, the structural optimization of copper–organic complexes for combinations with the reducing agents should include uncharged organic ligands that carry hard electronegative inorganic

  铜有机化合物作为有效的抗肿瘤候选药物获得了广泛的关注，这主要是因为它们能够在外源还原剂触发的 Cu2+ 转变为 Cu1+ 时产生氧化爆发。我们报道了一系列 Cu(II)-有机复合物与 N-乙酰半胱氨酸 (NAC) 孵育后产生活性氧 (ROS) 和细胞死亡的不同效力。为了深入了解有机配体优化的结构先决条件，我们研究了 Cu(II) 与吡啶亚甲基硫代乙内酰脲、吡啶基苯并噻唑、吡啶基苯并咪唑、缩氨基硫脲和卟啉配合物的电化学性质和细胞毒性。我们证明，复合物与 NAC 结合杀死细胞的能力是由 Cu+2 → Cu+1 氧化还原转变的电位决定的，而不是由有机配体的空间结构决定的。为了使电池对铜有机络合物敏感，金属还原的电化学电位应低于还原剂的氧化电位。一般来说，与还原剂结合的铜有机配合物的结构优化应包括携带硬电负性无机部分的不带电有机配体。