[(5-nitro-2-oxoindol-3-yl)amino]thiourea | 1140892-35-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(5-nitro-2-oxoindol-3-yl)amino]thiourea
• CAS: 1140892-35-8；28284-09-5
• 化学式: C₉H₇N₅O₃S
• 分子量: 265.252
• InChiKey: AUTJKSKBEGPKCN-UHFFFAOYSA-N

物化性质

• 熔点：
  232 °C(Solv: methanol (67-56-1))
• 密度：
  1.85±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.08
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  122.65
• 氢给体数：
  3.0
• 氢受体数：
  5.0

文献信息

• Assessment of 5-substituted Isatin as Surface Recognition Group: Design, Synthesis, and Antiproliferative Evaluation of Hydroxamates as Novel Histone Deacetylase Inhibitors
  作者：Avineesh Singh、Kamlesh Raghuwanshi、Vijay K Patel、Deepak K Jain、Ravichandran Veerasamy、Anshuman Dixit、Harish Rajak

  DOI：10.1007/s11094-017-1616-1

  日期：2017.8

  Histone deacetylase (HDAC) is a promising target for cancer treatment. HDAC inhibitors consist of three pharmacophoric features: an aromatic cap group, zinc binding group (ZBG), and a linker chain connecting cap group to ZBG. Herein, we report on (i) substituted isatin moiety as the cap group that recognizes the surface of active enzyme pocket and (ii) thiosemicarbazide moiety incorporated as linker group responsible for connecting the cap group to ZBG (hydroxamic acid). The synthesized compounds were evaluated for their antiproliferative activity and HDAC enzyme inhibition. The binding mode analysis of proposed compounds was evaluated by docking studies. Several analogs were found to inhibit HDAC and cellular proliferation of Hela cervical cancer cells, with GI50 values in the micromolar range. One compound (Vd) was found to have greater in vitro antiproliferative activity in comparison to other compounds.

  组蛋白去乙酰化酶（HDAC）是癌症治疗的潜在靶点。HDAC抑制剂由三种药效团特征组成：芳香的帽状基团、锌结合基团（ZBG）以及连接帽状基团与ZBG的链接链。本文报道了（i）取代的异吲哚酮部分作为帽状基团，识别活性酶口袋表面，以及（ii）结合为链接基团负责连接帽状基团与ZBG（羟肟酸）的酰肼部分。所合成的化合物进行了抗增殖活性和HDAC酶抑制活性的评估。通过对接研究评估了所提出化合物的结合模式。发现多个类似物能够抑制HDAC及宫颈癌Hela细胞的增殖，其GI50值在微摩尔范围内。其中一个化合物（Vd）相较于其他化合物显示出更强的体外抗增殖活性。
• Synthesis and evaluation of isatin derivatives as corrosion inhibitors for Q235A steel in highly concentrated HCl
  作者：Gang Chen、Hui-jun Su、Ying-pan Song、Yu Gao、Jie Zhang、Xiao-jiang Hao、Jing-rui Zhao

  DOI：10.1007/s11164-012-0870-9

  日期：2013.10

  A series of inhibitors—isatin derivatives aimed at anticorrosion of Q235A steel—was synthesized. The molecule structures were analyzed by NMR and MS. The inhibition on the corrosion in a concentrated HCl solution as high as 3 M was studied by weight loss, molecular simulation, and potentiodynamic polarization. The results indicate that isatin derivatives act as mixed type (cathodic/anodic) inhibitors. Several compounds were investigated in the formulations, during which compound 6 shows 95.5 % inhibition efficiency under the concentration of 100 mg/L accompanied by urotropine and 1,4-dihydroxy-2-butyne.

  一系列抑制剂——旨在防止Q235A钢腐蚀的靛红衍生物——被合成出来，并通过NMR和MS分析了分子结构。通过失重法、分子模拟和动电位极化法研究了这些衍生物在高达3M浓盐酸溶液中的抑制腐蚀作用。结果表明，靛红衍生物具有混合型（阴极/阳极）抑制剂的作用。在配方中研究了几种化合物，其中化合物6在100mg/L浓度下与乌洛托品和1,4-二羟基-2-丁炔共同作用时表现出95.5%的抑制效率。
• Sulfur-Containing Schiff Base Complexes of Iron(III) and Lead(II): Synthesis, Characterization, Antimicrobial Activity, and Their Electrochemical Behaviors
  作者：Sachin Malik、Mamta Kumari、Shikha Chauhan、D. K. Sharma

  DOI：10.1080/10426500903299869

  日期：2010.7.30

  thiosemicarbazide with respective ketones in 1:1 molar ratio in ethanol medium. Lead and iron complexes were prepared by the reaction of lead(II) chloride and iron(III) chloride with the ligands in a 1:2 molar ratio, respectively. The newly synthesized complexes have been characterized by elemental analysis, melting point determinations, and UV, ESR, and IR spectral studies. In all the complexes, the monobasic

  硫-氮供体配体，5-硝基-1H-吲哚-2,3-二酮和6-硝基-1H-吲哚-2,3-二酮和5-氯-1H-吲哚-2,3-二酮的缩氨基硫脲已通过氨基硫脲与相应酮以 1:1 摩尔比在乙醇介质中缩合制备。铅和铁配合物是通过氯化铅 (II) 和氯化铁 (III) 分别与配体以 1:2 的摩尔比反应制备的。新合成的配合物已通过元素分析、熔点测定以及 UV、ESR 和 IR 光谱研究进行表征。在所有配合物中，配体的一元二齿性质是明显的。基于分析和光谱数据，提出了铅的六配位结构和铁配合物的五配位结构。已经对这些化合物针对各种致病细菌和真菌菌株进行了抗菌和抗真菌研究。筛选了其中一种配体及其金属配合物的抗生育活性。补充材料可用于本文。转至出版商在线版的磷、硫和硅及相关元素，查看免费的补充文件。
• Synthetic, spectral, and antimicrobial aspects of biologically relevant coordination compounds of dioxomolybdenum(VI) and oxovanadium(V)
  作者：R. Garg、N. Fahmi、R. V. Singh

  DOI：10.1134/s1070328408030093

  日期：2008.3

  Heterocyclic ketimines, 5-nitro-3-(indolin-2-one)hydrazinecarbothioamide (L1H), 5-nitro-3-(indolin-2-one)hydrazinecarboxamide (L2H), 6-nitro-3-(indolin-2-one)hydrazinecarbo-thioamide (L3H), and 6-nitro-3-(indolin-2-one) hydrazinecarboxamide (L4H), were prepared by the condensation of thiosemicarbazide and semicarbazide hydrochloride (in the presence of sodium acetate) in ethanol with the respective ketones. The dioxomolybdenum(VI) complexes and oxovanadium(V) complexes have been prepared by mixing dioxobis(2,4-pentanedinato)molybdenum(VI) in 1: 2 molar ratios and vanadium oxytrichloride in 1: 1 and 1: 2 molar ratios with monobasic bidentate ketimines. The resulting complexes have been characterized by elemental analysis, conductance measurements, and spectral studies, including IR, 1H NMR, and UV spectra. The ketimines and their corresponding metal complexes have been tested on a number of pathogenic bacteria and fungi in order to assess their growth inhibition potency at different concentrations.

  杂环酮亚胺、5-硝基-3-(吲哚啉-2-酮)肼基硫代甲酰胺(L1H)、5-硝基-3-(吲哚啉-2-酮)肼基甲酰胺(L2H)、6-硝基-3-(吲哚啉-2-酮)肼基硫代甲酰胺(L3H)、和 6-硝基-3-（吲哚啉-2-酮）肼甲酰胺（L4H）是由硫代氨基脲和盐酸氨基脲（在乙酸钠存在下）在乙醇中与相应的酮缩合制备的。二氧二钼(VI)络合物和氧钒(V)络合物是通过将摩尔比为 1:2 的二氧双(2,4-戊二酸)钼(VI)和摩尔比为 1:1 和 1:2 的氧三氯化钒与单碱基双齿酮亚胺混合而制备的。通过元素分析、电导测量和光谱研究（包括红外光谱、1H NMR 光谱和紫外光谱），对所得复合物进行了表征。这些酮亚胺及其相应的金属复合物已在一些病原细菌和真菌上进行了测试，以评估它们在不同浓度下的生长抑制效力。
• Electrochemical characterization of isatin-thiosemicarbazone derivatives
  作者：Juliano da Rosa Justim、Lucas Martins Correa Bohs、Bianca Barreto Martins、Katlen Christian Tribuzy Bandeira、Ana Paula Lopes de Melo、Vanessa Carratu Gervini、Leandro Bresolin、Marcelo Godoi、Carlos Roberto de Menezes Peixoto

  DOI：10.1007/s12039-021-01970-x

  日期：2021.12

  isatin-3-(N4-benzylthiosemicarbazone) (ITSC-Ph), 1-(5-nitro-2-oxoindolin-3-ylidene)thiosemicarbazide (NO2-ITSC) and 1-(5-nitro-2-oxoindolin-3-ylidene)-4-phenylthiosemicarbazide (NO2-ITSC-Ph) have demonstrated an irreversible oxidation process. More specifically, the generation of isatin and thiourea moieties as the final oxidation products was proposed. The cyclic voltammograms also demonstrate irreversible

  摘要 在此，我们特别描述了四种靛红-缩氨基硫脲衍生物的电化学行为。在这方面，靛红-3-氨基硫脲 ( ITSC )、靛红-(N 4 -苄基氨基硫) ( ITSC​​-Ph )、1-(5-硝基-2-氧代吲哚-3-亚基)氨基硫脲 ( NO ) 的循环伏安图2 -ITSC ) 和 1-(5-nitro-2-oxoindolin-3- ylidene )-4-phenylthiosemicarbazide ( NO 2 -ITSC-Ph ) 已经证明了不可逆的氧化过程。更具体地说，提出了作为最终氧化产物的靛红和硫脲部分的产生。循环伏安图还证明了ITSC和ITSC​​-Ph分三个步骤。建议的最终产品是 3-aminoindolin-2-one 和硫脲部分。在NO 2 -ITSC和NO 2 -ITSC-Ph的循环伏安图中，观察到五个还原过程：其中三个是由于硝基的还原。有人提出 5-hydroxyamin