N(4)-methyl-4-nitroacetophenone thiosemicarbazone | 72488-46-1

• 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: N(4)-methyl-4-nitroacetophenone thiosemicarbazone
• 英文别名: N(4-)methyl-4-nitroacetophenone thiosemicarbazone；N4-methyl-4-nitroacetophenone thiosemicarbazone；p-nitroacetophenone 4-methylthiosemicarbazone；H4NO2Ac4M；1-Methyl-3-[1-(4-nitrophenyl)ethylideneamino]thiourea
• CAS: 72488-46-1
• 化学式: C₁₀H₁₂N₄O₂S
• 分子量: 252.297
• InChiKey: BDCREANJEYMDCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(η3-C4H7)Pt(μ-Cl)]2 、 N(4)-methyl-4-nitroacetophenone thiosemicarbazone 以 丙酮 为溶剂， 以62%的产率得到[Pt(p-nitroacetophenone 4-methylthiosemicarbazone-2H)]4
  参考文献：
  名称：

  对硝基苯乙酮 4-甲基氨基硫脲铂化过程中中间体的分离：作为抗肿瘤药物的潜在应用

  摘要：

  对 Pd 和 Pt 缩氨基硫脲复合物的形成和反应性的研究揭示了一种未经研究的中间体，该中间体源自对硝基苯乙酮 4-甲基缩氨基硫脲 (L1H2)。L1H2 配体导致新的复合物 [Pt(L1)(L1H2)]，支持环金属化反应发生的假设机制。所有新合成的复合物 [(Pd(L1)4]、[(Pt(L1)4] 和 [Pt(L1)(L1H2)] (3) 均已针对 MCF7、SF268 和 NCI 进行表征和测试H460 细胞系。报道了 [Pt(L1)(L1H2)]·dmso 的晶体结构。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2008）

  DOI：

  10.1002/ejic.200800003
• 作为产物：
  描述：

  4-甲基氨基硫脲 、 对硝基苯乙酮 在 硫酸 作用下， 以 乙醇 为溶剂， 生成 N(4)-methyl-4-nitroacetophenone thiosemicarbazone
  参考文献：
  名称：

  Coordination of nitro-thiosemicarbazones to ruthenium(II) as a strategy for anti-trypanosomal activity improvement

  摘要：

  Complexes [RuCl(H4NO(2)Fo4M)(bipy)(dppb)]PF6 (1), [RuCl(H4NO(2)Fo4M)(Mebipy)(dppb)]PF6 (2), [RuCl(H4NO(2)Fo4M)(phen)(dppb)]PF6 (3), [RuCl(H4NO(2)Ac4M)(bipy)(dppb)]PF6 (4), [RuCl(H4NO(2)Ac4M)(Mebipy)(dppb)]PF6 (5) and [RuCl(H4NO(2)Ac4M)(phen)(dppb)]PF6 (6) with N-4-methyl-4-nitrobenzalde hyde thiosemicarbazone (H4NO(2)Fo4M) and N-4-methyl-4-nitroacetophenone thiosemicarbazone (H4NO(2) Ac4M) were obtained from [RuCl2(bipy)(dppb)], [RuCl2(Mebipy)(dppb)], and [RuCl2(phen)(dppb)], (dppb = 1,4-bis(diphenylphospine)butane; bipy = 2,2'-bipyridine: Mebipy = 4,4'-dimethyl-2,2'-bipyridine: phen = 1,10-phenanthroline). In all cases the thiosemicarbazone is attached to the metal center through the sulfur atom.Complexes (1-6), together with the corresponding ligands and the Ru precursors were evaluated for their ability to in vitro suppress the growth of Trypanosoma cruzi. All complexes were more active than their corresponding ligands and precursors. Complexes (1-3) and (5) revealed to be the most active among all studied compounds with ID50 = 0.6-0.8 mu M.In all cases the association of the thiosemicarbazone with ruthenium, dppb and bipyridine or phenanthroline in one same complex proved to be an excellent strategy for activity improvement. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.03.005

文献信息

• N(4)-Methyl-4-nitroacetophenone thiosemicarbazone and its nickel(II) complex: Experimental and theoretical structural studies
  作者：Anayive Pérez-Rebolledo、Isolda C. Mendes、Nivaldo L. Speziali、Philippe Bertani、Jarbas M. Resende、Antônio F. de Carvalho Alcântara、Heloisa Beraldo

  DOI：10.1016/j.poly.2006.11.012

  日期：2007.5

  N(4)-Methyl-4-nitroacetophenone thiosemicarbazone (H4NO2Ac4M, 1) and its nickel(II) complex ([Ni(4NO2Ac4M)2], 2) were obtained and fully characterized. Compound 1 crystallizes in the triclinic P1¯ space group and adopts the 1-E,E configuration in relation to the imino and thioamide groups, respectively. NMR data along with HF/6-31G∗ and DFT/BLYP/6-31G∗ theoretical calculations of energies and of 1H

  获得并充分表征了N（4）-甲基-4-硝基苯乙酮硫代半碳酮（H4NO 2 Ac4M，1）及其镍（II）配合物（[Ni（4NO 2 Ac4M）2 ]，2）。化合物1在三斜P1空间基团中结晶，并且相对于亚氨基和硫代酰胺基团分别采用1 - E，E构型。NMR数据一起用HF / 6-31G *和DFT / BLYP / 6-31G *的能量的和理论计算1 H和13角的优化构型C NMR化学位移1提示1 - E，E异构体可能存在于DMSO- d 6中，1 - Z，E异构体存在于CDCl 3中。化合物2在单斜C 2 / c空间群中结晶。硫代半氨基甲酮通过N–S螯合系统进行配位，硫原子彼此之间处于顺式位置。在晶体的两个配位体采用ê配置在相对于亚氨基，2 -顺（ë -镍- ë）。但是，固态（粉末）以及溶液（DMSO- d 6）NMR数据以及HF / 6-31G *和DFT / BLYP / 6-31G *的计算方法，可得到1
• In vitro anti-proliferative, and in silico ribonucleotide reductase and pharmacokinetics studies of heteroleptic silver(I), nickel(II) and copper(II) complexes of 4-methyl-3-thiosemicarbazones and ibuprofen
  作者：Sundaram Bharathi、Dharmasivam Mahendiran、Sumeer Ahmed、Aziz Kalilur Rahiman

  DOI：10.1016/j.jtemb.2023.127211

  日期：2023.9

  reducing ability of the complexes. In vitro anti-proliferative studies by MTT assay, apoptotic behaviour and cellular uptake studies were investigated followed by the in silico interaction with ribonucleotide reductase (RNR) enzyme. Results The spectral studies predicted distorted tetrahedral geometry around silver(I) ion and distorted octahedral geometry around nickel(II) and copper(II) ions. The reducing

  目标 目前的研究重点是通式[ Ag (L 1−4 )(ibu)] ( 1 – 4 ) 和 [M( L 1−4 )(ibu) 2 ] ( 5 – 12 )，其中 L 1−4 = 2-(1-(4-取代苯基)亚乙基)- N-甲基肼硫甲酰胺，ibu = 非甾体类抗炎药（布洛芬） )，M = Cu(II) 和 Ni(II)。 方法 使用各种光谱技术来验证合成复合物的结构。采用紫外-可见光和循环伏安技术分析了配合物的稳定性和还原能力。通过 MTT 测定、细胞凋亡行为和细胞摄取研究进行体外抗增殖研究，然后研究与核糖核苷酸还原酶 (RNR) 的计算机相互作用。 结果 光谱研究预测了银（I）离子周围的扭曲四面体几何形状以及镍（II）和铜（II）离子周围的扭曲八面体几何形状。使用抗坏血酸，通过紫外-可见光和循环伏安技术分析铜(II)络合物的还原能力，验证了络合物的还原能力以及细胞内可能的相互作用。合成复合物对
• Manganese(II) complexes with N4-methyl-4-nitrobenzaldehyde, N4-methyl-4-nitroacetofenone, and N4-methyl-4-nitrobenzophenone thiosemicarbazone: Investigation of in vitro activity against Trypanosoma cruzi
  作者：Denise da Gama Jaén Batista、Patrícia Bernardino da Silva、Daniela R. Lachter、Renata S. Silva、Ricardo Q. Aucelio、Sonia R.W. Louro、Heloisa Beraldo、Maria de Nazaré C. Soeiro、Letícia R. Teixeira

  DOI：10.1016/j.poly.2010.04.023

  日期：2010.7

  Thiosemicarbazones are known to be active against different pathogenic microorganisms including Trypanosoma cruzi, the etiological agent of Chagas disease. In the search for new therapeutic drugs against this illness, the complexes [Mn(H4NO(2)Fo4M)(2)Cl-2] (1), [Mn(H(4)NO(2)Ac4M)(2)Cl-2] (2) and [Mn(H4NO(2) Bz4M)(2)Cl-2] (3) of N-4-methyl-4-nitrobenzaldehyde thiosemicarbazone (H4NO(2)Fo4M), N-4-methyl-4-nitroacetophenone thiosemicarbazone (H4NO(2)Ac4M) and N-4-methyl-4-nitrobenzophenone thiosemicarbazone (H4NO(2)Bz4M) were obtained and screened in vitro against bloodstream and intracellular forms of T. cruzi. H4NO(2)Fo4M, H4NO(2)Ac4M and their Mn(II) complexes displayed poor effect on bloodstream trypomastigotes, with IC50 values ranging from 68 to >200 mu M. However, although H4NO(2)Bz4M was also not active, its corresponding Mn(II) complex presented high effect on this T. cruzi form, with an IC50 value of 19 mu M. The effect of complex (3), against trypomastigotes of T. cruzi supports further in vitro as well as in vivo studies. (C) 2010 Elsevier Ltd. All rights reserved.
• Coordination of nitro-thiosemicarbazones to ruthenium(II) as a strategy for anti-trypanosomal activity improvement
  作者：Claudia Rodrigues、Alzir A. Batista、Javier Ellena、Eduardo E. Castellano、Diego Benítez、Hugo Cerecetto、Mercedes González、Letícia R. Teixeira、Heloisa Beraldo

  DOI：10.1016/j.ejmech.2010.03.005

  日期：2010.7

  Complexes [RuCl(H4NO(2)Fo4M)(bipy)(dppb)]PF6 (1), [RuCl(H4NO(2)Fo4M)(Mebipy)(dppb)]PF6 (2), [RuCl(H4NO(2)Fo4M)(phen)(dppb)]PF6 (3), [RuCl(H4NO(2)Ac4M)(bipy)(dppb)]PF6 (4), [RuCl(H4NO(2)Ac4M)(Mebipy)(dppb)]PF6 (5) and [RuCl(H4NO(2)Ac4M)(phen)(dppb)]PF6 (6) with N-4-methyl-4-nitrobenzalde hyde thiosemicarbazone (H4NO(2)Fo4M) and N-4-methyl-4-nitroacetophenone thiosemicarbazone (H4NO(2) Ac4M) were obtained from [RuCl2(bipy)(dppb)], [RuCl2(Mebipy)(dppb)], and [RuCl2(phen)(dppb)], (dppb = 1,4-bis(diphenylphospine)butane; bipy = 2,2'-bipyridine: Mebipy = 4,4'-dimethyl-2,2'-bipyridine: phen = 1,10-phenanthroline). In all cases the thiosemicarbazone is attached to the metal center through the sulfur atom.Complexes (1-6), together with the corresponding ligands and the Ru precursors were evaluated for their ability to in vitro suppress the growth of Trypanosoma cruzi. All complexes were more active than their corresponding ligands and precursors. Complexes (1-3) and (5) revealed to be the most active among all studied compounds with ID50 = 0.6-0.8 mu M.In all cases the association of the thiosemicarbazone with ruthenium, dppb and bipyridine or phenanthroline in one same complex proved to be an excellent strategy for activity improvement. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Isolation of an Intermediate in the Platination of <i>p</i> ‐Nitroacetophenone 4‐Methylthiosemicarbazone: Potential Application as an Antitumor Drug
  作者：Adoración G. Quiroga、Leticia Cubo、Pablo J. Sanz Miguel、Victoria Moneo、Amancio Carnero、Carmen Navarro‐Ranninger

  DOI：10.1002/ejic.200800003

  日期：2008.3

  Pd and Pt thiosemicarbazone complexes has revealed an unstudied intermediate derived from p-nitroacetophenone 4-methylthiosemicabazone (L1H2). The L1H2 ligand leads to a new complex [Pt(L1)(L1H2)] that supports the postulated mechanism of how cyclometallation reactions take place. All the newly synthesized complexes, [(Pd(L1)4], [(Pt(L1)4], and [Pt(L1)(L1H2)] (3), have been characterized and tested against

  对 Pd 和 Pt 缩氨基硫脲复合物的形成和反应性的研究揭示了一种未经研究的中间体，该中间体源自对硝基苯乙酮 4-甲基缩氨基硫脲 (L1H2)。L1H2 配体导致新的复合物 [Pt(L1)(L1H2)]，支持环金属化反应发生的假设机制。所有新合成的复合物 [(Pd(L1)4]、[(Pt(L1)4] 和 [Pt(L1)(L1H2)] (3) 均已针对 MCF7、SF268 和 NCI 进行表征和测试H460 细胞系。报道了 [Pt(L1)(L1H2)]·dmso 的晶体结构。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2008）