1-(5-nitro-2-oxoindolin-3-ylidene)-4-phenylthiosemicarbazide | 301819-87-4

• 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: 1-(5-nitro-2-oxoindolin-3-ylidene)-4-phenylthiosemicarbazide
• 英文别名: 1-[(5-nitro-2-oxoindol-3-yl)amino]-3-phenylthiourea
• CAS: 301819-87-4
• 化学式: C₁₅H₁₁N₅O₃S
• mdl: MFCD00991969
• 分子量: 341.35
• InChiKey: AXGFKEGXFBHFJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  108.66
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  哌啶 、 聚合甲醛 、 1-(5-nitro-2-oxoindolin-3-ylidene)-4-phenylthiosemicarbazide 以 乙醇 为溶剂， 反应 4.0h， 以94%的产率得到1-piperidinomethyl-5-nitro-1H-indole-2,3-dione-3-(4-phenylthiosemicarbazone)
  参考文献：
  名称：

  Synthesis and primary cytotoxicity evaluation of new 5-nitroindole-2,3-dione derivatives

  摘要：

  A new series of 5-nitro-1H-indole-2,3-dione-3-thiosemicarbazones (3a-k) obtained by condensation of 5-nitro-1H-indole-2,3dione (1) with N-substituted-thiosemicarbazides (2a-k) were treated with morpholine or piperidine and formaldehyde to yield 1-morpholino/piperidinomethyl-5-nitroindole-2 3-dione-3-thiosemicarbazones (4a-m). The structures of all the compounds were determined by analytical and spectral (IR, H-1-NMR, EIMS) methods. Compounds 3b, 3c, 3f, 3k, 4a, 4c, 4f and 4l chosen as prototypes were evaluated in the National Cancer Institute's 3-cell line, one dose in vitro primary cytotoxicity assay. All the compounds that passed the criteria for activity in this assay were scheduled automatically for evaluation against the full panel of 60 human tumour cell lines at a minimum of five concentrations at 10-fold dilutions. Sulphorhodamine B (SRB) protein assay was used to estimate cell stability or growth. The most active compound was found to be 1-morpholinomethyl-5-nitroindole-2,3-dione-3-N(chlorophenyl)thiosemicarbazone (4l). This compound demonstrated the most marked effects in the National Cancer Institute's 60 human tumour cell line in vitro screen on a non-small cell lung cancer cell line (HOP-62, logo GI(50) value < -8.00) and on leukaemia cell lines (HL-60(TB), log(10) GI(50) value -6.30; MOLT-4, log(10) GI(50) value -6.18). (C) 2002 Published by Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(02)01416-2
• 作为产物：
  描述：

  5-硝基靛红 、 4-苯基-3-硫代氨基脲 在 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以69%的产率得到1-(5-nitro-2-oxoindolin-3-ylidene)-4-phenylthiosemicarbazide
  参考文献：
  名称：

  一些新型 N4 取代的 5-Nitroisatin-3-氨基硫脲的合成及脲酶抑制特性

  摘要：

  4-取代的 5-nitroisatin-3-thiosemicarbazones 2a-2q 已被合成并筛选了体外脲酶抑制活性。发现化合物 2a-2d、2g、2i、2j 和 2q 是该酶的有效抑制剂。其中，2c 表现出有效的抑制活性，IC50 值为 16.4 μM，可作为进一步研究的先导分子。构效关系研究表明，取代基的电子效应在合成化合物的脲酶抑制潜力中起着重要作用。ery program (15-21), 我们最近合成了许多 N 4 - 取代的靛红-3-缩氨基硫脲作为脲酶抑制剂，具有无毒性质 (22, 23)。这些发现为进一步研究此类化合物以开发更有效、安全和有用的脲酶抑制剂奠定了坚实的基础。此外，构效关系 (SAR) 研究表明，苯环上取代基的类型和位置，在氨基硫脲部分的 N 4 处取代，在这些化合物的脲酶抑制潜力中起重要作用。为了进一步增强新的抗脲酶化合物的活性，研究了在靛红支架的 5

  DOI：

  10.2174/157018010790225840

文献信息

• Synthesis and Urease Inhibitory Properties of Some New N4-Substituted 5-Nitroisatin-3-thiosemicarbazones
  作者：Humayun Pervez、Nazia Manzoor、Muhammad Yaqub、Ajmal Khan、Khalid Khan、Faiz-ul-Hassan Nasim、M. Choudhary

  DOI：10.2174/157018010790225840

  日期：2010.2.1

  with the synthesis and evaluation of urease inhibitory potential of a series of seventeen N 4 - arylsubstituted 5-nitroisatin-3-thiosemicarbazones. We describe here the effects of the nature of aryl groups at N 4 (modified by placement of one or two substituents about the phenyl ring) and the presence of nitro function at position-5 of the isatin scaffold on the urease inhibitory potential of these compounds

  4-取代的 5-nitroisatin-3-thiosemicarbazones 2a-2q 已被合成并筛选了体外脲酶抑制活性。发现化合物 2a-2d、2g、2i、2j 和 2q 是该酶的有效抑制剂。其中，2c 表现出有效的抑制活性，IC50 值为 16.4 μM，可作为进一步研究的先导分子。构效关系研究表明，取代基的电子效应在合成化合物的脲酶抑制潜力中起着重要作用。ery program (15-21), 我们最近合成了许多 N 4 - 取代的靛红-3-缩氨基硫脲作为脲酶抑制剂，具有无毒性质 (22, 23)。这些发现为进一步研究此类化合物以开发更有效、安全和有用的脲酶抑制剂奠定了坚实的基础。此外，构效关系 (SAR) 研究表明，苯环上取代基的类型和位置，在氨基硫脲部分的 N 4 处取代，在这些化合物的脲酶抑制潜力中起重要作用。为了进一步增强新的抗脲酶化合物的活性，研究了在靛红支架的 5
• [EN] THIOSEMICARBAZONES WITH MDR1 - INVERSE ACTIVITY<br/>[FR] THIOSEMICARBAZONES À ACTIVITÉ ANTI-MDR1
  申请人：US HEALTH

  公开号：WO2012033601A1

  公开（公告）日：2012-03-15

  Disclosed herein are drug compounds that have MDR-inverse activity and thus are effective against multidrug-resistant cells. Exemplary compounds disclosed herein have the structure;Formula (I). Examples of the disclosed compounds have been found to have, inter alia, efficacy in directly treating multidrug resistant cells, rendering multidrug resistant cells susceptible to other chemotherapeutics and in some instances reversing multidrug resistance.

  本文披露了具有MDR逆转活性的药物化合物，因此对多药耐药细胞有效。本文披露的示例化合物具有下列结构；公式（I）。已发现披露的化合物的示例具有直接治疗多药耐药细胞的功效，使多药耐药细胞对其他化疗药物敏感，并在某些情况下逆转多药耐药。
• Palladium(II) complexes of 5-substituted isatin thiosemicarbazones: Synthesis, spectroscopic characterization, biological evaluation and <i>in silico</i> docking studies
  作者：Gandham Munikumari、Ramaiah Konakanchi、Venkata Bharat Nishtala、Gondru Ramesh、Laxma Reddy Kotha、K. B. Chandrasekhar、Chennuru Ramachandraiah

  DOI：10.1080/00397911.2018.1546400

  日期：2019.1.2

  antibacterial activity against B. subtilis and K. pneumoniae and also complex 2 has shown good antifungal activity against the micro organisms. The antioxidant activity analysis revealed that the complex 3 showed significant activity with IC50 values 7.24 ± 0.09 µM. Moreover, the in vitro antiproliferative activity results suggested that complex 3 exhibited high activity against HeLa cell line compared with

  摘要 通过取代的靛红分子与 N(4)-苯基-3-氨基硫脲缩合，合成了取代杂环 (靛红) 附加的氨基硫脲配体 (L1-L3)。钯 (II) 配合物由配体 (L1-L3) 和 PdCl2 合成，通式为 [PdCl(X-C15H10N4OS)]，其中 X = 5-氯 (1)、5-溴 (2) 和 5-硝基（3）。分析和光谱方法都已用于分析和表征合成的化合物。抗菌活性结果观察到，复合物 1 和 2 对枯草芽孢杆菌和肺炎克雷伯菌具有强大的抗菌活性，并且复合物 2 对微生物也显示出良好的抗真菌活性。抗氧化活性分析表明，复合物 3 显示出显着的活性，IC50 值为 7.24 ± 0.09 µM。此外，体外抗增殖活性结果表明，与标准品相比，复合物 3 对 HeLa 细胞系表现出较高的活性，IC50 值为 16.52 ± 1.08 µM。对接结果相关性很好。图形概要
• Isatin thiosemicarbazone-blended polymer films for biomedical applications: surface morphology, characterisation and preliminary biological assessment
  作者：David Mallinson、Polyxeni Alexiou、Alexander B. Mullen、Maria Pelecanou、Marina Sagnou、Dimitrios A. Lamprou

  DOI：10.1039/c6ra01224h

  日期：——

  Poly(methyl methacrylate) and polyurethane are polymers currently used for a range of biomedical applications. To modify their surface characteristics, biocompatibility, and potentially reduce any related side effects, the addition to the polymers of appropriate compounds has been investigated. Isatin thiosemicarbazone derivatives were synthesised and added to poly(methyl methacrylate) and polyurethane

  聚甲基丙烯酸甲酯和聚氨酯是目前用于一系列生物医学应用的聚合物。为了改变它们的表面特性，生物相容性并潜在地减少任何相关的副作用，已经研究了向聚合物中添加适当化合物的方法。合成了isatin thiosemicarbazone衍生物并将其添加到聚（甲基丙烯酸甲酯）和聚氨酯溶液中，然后将它们旋涂到二氧化硅晶片上。所得膜通过接触角测角法和原子力显微镜表征。由四氢呋喃溶剂制得的PMMA薄膜显示出高度疏水的蜂窝状结构。但是，这种变化在聚氨酯表面看不到。使用PNT2A前列腺细胞研究了细胞毒性和对聚合物表面细胞增殖的影响。
• Synthesis and structure–antituberculosis activity relationship of 1H-indole-2,3-dione derivatives
  作者：Nilgün Karalı、Aysel Gürsoy、Fatma Kandemirli、Nathaly Shvets、F. Betül Kaynak、Süheyla Özbey、Vasyl Kovalishyn、Anatholy Dimoglo

  DOI：10.1016/j.bmc.2007.05.063

  日期：2007.9.1

  New series of 5-fluoro-1H-indole-2,3-dione-3-thiosemicarbazones 2a-k and 5-fluoro-l-morpholino/piperidinomethyl-1Hindole-2,3-dione-3-thiosemicarbazones 3a-r were synthesized. The structures of the synthesized compounds were confirmed by spectral data, elemental and single crystal X-ray diffraction analysis. The new 5-fluoro-IH-indole-2,3-dione derivatives, along with previously reported 5-nitro-1H-indole-2,3-dione-3-thiosemicarbazones 2l-v, 1-morpholino/piperidinomethyl-5-nitro-1H-indole-2,3dione-3-thiosemicarbazones 4a-1, and 5-nitro-1H-indole-2,3-dione-3-[(4-oxo-1,3-thiazolidin-2-ylidene)hydrazones] 5a-s, were evaluated for in vitro antituberculosis activity against Mycobacterium tuberculosis H37Rv. Among the tested compounds, 5-nitro-1H-indole-2,3-dione-3-thiosemicarbazones (2p, 2r, and 2s) and its 1-morpholinomethyl derivatives (4a, 4e, 4g, and 4i) exhibited significant inhibitory activity in the primary screen. The antituberculosis activity of molecules with diverse skeletons was investigated by means of the Electronic-Topological Method (ETM). Ten pharmacophores and ten anti-pharmacophores that have been found by this form the basis of the system capable of predicting the structures of potentially active compounds. The forecasting ability of the system has been tested on structures that differ from those synthesized. The probability of correct identification for active compounds was found as equal to 93% in average. To obtain the algorithmic base for the activity prediction, Artificial Neural Networks were used after the ETM (the so-called combined ETM-ANN method). As the result, only 9 pharmacophores and anti-pharmacophores were chosen as the most important ones for the activity. By this, ANNs classified correctly 94.4%, or 67 compounds from 71. (c) 2007 Elsevier Ltd. All rights reserved.