(Z)-N-methyl-2-(5-nitro-2-oxoindolin-3-ylidene)hydrazinecarbothioamide | 341929-70-2

• 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: (Z)-N-methyl-2-(5-nitro-2-oxoindolin-3-ylidene)hydrazinecarbothioamide
• 英文别名: 1-methyl-3-[(5-nitro-2-oxoindol-3-yl)amino]thiourea
• CAS: 341929-70-2
• 化学式: C₁₀H₉N₅O₃S
• 分子量: 279.279
• InChiKey: VQAHVILDHIKPTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.34
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  (Z)-N-methyl-2-(5-nitro-2-oxoindolin-3-ylidene)hydrazinecarbothioamide 、 potassium tetrachloroplatinate(II) 以 乙醇 为溶剂， 反应 2.0h， 以78%的产率得到
  参考文献：
  名称：

  靛红硫半脲酮衍生物的铂（II）配合物的合成：体外抗癌和脱氧核糖核酸结合活性

  摘要：

  摘要通过铂（II）与以下物质的反应，合成了六种新的具有半胱氨酸部分[PtL1至Pt（L6）2]的硫半脲席夫碱的铂（II）配合物：（Z）-2-（2-氧代吲哚- 3-亚苯基）-N-苯基肼甲硫酰胺[L1H]，（Z）-2-（5-甲基-2-氧吲哚-3-亚基）-N-苯基肼甲硫酰胺[L2H]，（Z）-2-（5-氟- 2-氧代吲哚-3-亚甲基）-N-苯基肼甲硫代酰胺[L3H]，（Z）-N-甲基-2-（5-硝基-2-氧代吲哚-3-亚基）肼碳硫代酰胺[L4H]，（Z）-N-甲基-2-（5-甲基-2-氧吲哚-3-亚甲基）肼甲硫代酰胺[L5H]和（Z）-N-乙基-2-（5-甲基-2-氧吲哚-3-亚甲基）肼甲硫代酰胺[L6H] 。这些复合物的结构通过元素分析，IR，UV-Vis，1H NMR和质谱分析进行了表征。通过单晶XRD进一步表征了Pt（L6）2的结构。这些复合物与小胸腺（CT）DNA的相互作用表现出较高的内在结合常数（Kb

  DOI：

  10.1016/j.ica.2014.03.029
• 作为产物：
  描述：

  5-硝基靛红 、 4-甲基氨基硫脲 以 乙醇 为溶剂， 反应 2.0h， 以80%的产率得到(Z)-N-methyl-2-(5-nitro-2-oxoindolin-3-ylidene)hydrazinecarbothioamide
  参考文献：
  名称：

  靛红硫半脲酮衍生物的铂（II）配合物的合成：体外抗癌和脱氧核糖核酸结合活性

  摘要：

  摘要通过铂（II）与以下物质的反应，合成了六种新的具有半胱氨酸部分[PtL1至Pt（L6）2]的硫半脲席夫碱的铂（II）配合物：（Z）-2-（2-氧代吲哚- 3-亚苯基）-N-苯基肼甲硫酰胺[L1H]，（Z）-2-（5-甲基-2-氧吲哚-3-亚基）-N-苯基肼甲硫酰胺[L2H]，（Z）-2-（5-氟- 2-氧代吲哚-3-亚甲基）-N-苯基肼甲硫代酰胺[L3H]，（Z）-N-甲基-2-（5-硝基-2-氧代吲哚-3-亚基）肼碳硫代酰胺[L4H]，（Z）-N-甲基-2-（5-甲基-2-氧吲哚-3-亚甲基）肼甲硫代酰胺[L5H]和（Z）-N-乙基-2-（5-甲基-2-氧吲哚-3-亚甲基）肼甲硫代酰胺[L6H] 。这些复合物的结构通过元素分析，IR，UV-Vis，1H NMR和质谱分析进行了表征。通过单晶XRD进一步表征了Pt（L6）2的结构。这些复合物与小胸腺（CT）DNA的相互作用表现出较高的内在结合常数（Kb

  DOI：

  10.1016/j.ica.2014.03.029

文献信息

• Synthesis, structure and <i>in vitro</i> anticancer, DNA binding and cleavage activity of palladium (II) complexes based on isatin thiosemicarbazone derivatives
  作者：Amna Qasem Ali、Siang Guan Teoh、Naser Eltaher Eltayeb、Mohamed B. Khadeer Ahamed、A.M.S. Abdul Majid、Arabya A.A. Almutaleb

  DOI：10.1002/aoc.3813

  日期：2017.12

  Six novel palladium(II) complexes of a thiosemicarbazone Schiff base with isatin moiety (PdL1 to PdL6) were synthesized by the reaction of palladium(II) with the following: (Z)‐2‐(2‐oxoindolin‐3‐ylidene)‐N‐phenylhydrazinecarbothioamide (L1H), (Z)‐2‐(5‐methyl‐2‐oxoindolin‐3‐ylidene)‐N‐phenylhydrazinecarbothioamide (L2H), (Z)‐2‐(5‐fluoro‐2‐oxoindolin‐3‐ylidene)‐N‐phenylhydrazinecarbothioamide (L3H),

  通过钯（II）与以下物质的反应，合成了六种新颖的硫半缩胺席夫碱与isatin部分（PdL1至PdL6）的钯（II）配合物：（Z）-2-（2-氧代吲哚-3-亚吡啶）- N-苯肼基甲硫基酰胺（L1H），（Z）-2-（5-甲基-2-氧代吲哚-3-亚基）-N-苯肼基甲硫基酰胺（L2H），（Z）-2-（5-氟-2-氧代吲哚-3 -亚甲基）-N-苯基肼甲硫酰胺（L3H），（Z）-N-甲基-2-（5-硝基-2-氧代吲哚-3-亚甲基）肼甲硫酰胺（L4H），（Z）-N-甲基-2-（- 5-甲基-2-氧代吲哚-3-亚丙基）肼甲硫酰胺（L5H）和（Z）-N-乙基-2-（5-甲基-2-氧代吲哚-3-基）肼碳硫代酰胺（L6H）。这些复合物的结构使用元素分析和红外，紫外可见，1 H NMR和质谱进行了表征。使用单晶X射线衍射进一步表征了PdL5的结构。这些复合物与小牛胸腺DNA的相互作用具有很高的固有结合常数（K b
• Design and synthesis of novel isatin-based derivatives targeting cell cycle checkpoint pathways as potential anticancer agents
  作者：Mohamed A. Yousef、Ahmed M. Ali、Wael M. El-Sayed、Wesam S. Qayed、Hassan H.A. Farag、Tarek Aboul-Fadl

  DOI：10.1016/j.bioorg.2020.104366

  日期：2020.12

  recent years, cell cycle and checkpoint pathways regulation are offering new therapeutic approaches against cancer. Isatin, is a well exploited scaffold in the anticancer domain. Accordingly, the current work describes the design and synthesis of two series of (Z)-3-substituted-2-(((E/Z)-5-substituted-2-oxo-1-substituted-indolin-3-ylidene)hydrazinylidene)-thiazolidin-4-ones, 4(a-s) and (E/Z)-1-subst

  近年来，细胞周期和检查点通路的调节正在为癌症提供新的治疗方法。靛红是一种在抗癌领域得到充分利用的支架。因此，目前的工作描述了两个系列（Z）-3-取代-2-（（（E / Z）-5-取代-2-氧代-1-取代-二氢吲哚-3-亚基）的设计和合成亚肼基)-噻唑烷-4-酮，4(as) 和 (E/Z)-1-取代-3-(((Z)-3-取代-4-甲基噻唑-2(3H)-亚基)亚肼基)- 5-取代-二氢吲哚-2-ones，5(as)。通过光谱和元素分析方法证实了合成分子的结构。用1 H- 1 H-NOESY进一步鉴定纯的非对映异构体，并用 X 射线晶体学证实。目标化合物在体外测试与多柔比星作为参考药物相比，它们对三种人类上皮细胞系、肝脏 (HepG2)、乳腺 (MCF-7) 和结肠 (HT-29) 以及二倍体人类正常细胞 (WI-38) 的细胞毒性。与正常的一种 WI-38 相比，三种癌细胞系报告了可变的细胞毒性作用
• Synthesis of isatin thiosemicarbazones derivatives: In vitro anti-cancer, DNA binding and cleavage activities
  作者：Amna Qasem Ali、Siang Guan Teoh、Abdussalam Salhin、Naser Eltaher Eltayeb、Mohamed B. Khadeer Ahamed、A.M.S. Abdul Majid

  DOI：10.1016/j.saa.2014.01.086

  日期：2014.5

  New derivatives of thiosemicarbazone Schiff base with isatin moiety were synthesized L1-L6. The structures of these compounds were characterized based on the spectroscopic techniques. Compound L6 was further characterized by XRD single crystal. The interaction of these compounds with calf thymus (CT-DNA) exhibited high intrinsic binding constant (k(b) = 5.03-33.00 x 10(5) M-1) for L1-L3 and L5 and (6.14-9.47 x 10(4) M-1) for L4 and L6 which reflect intercalative activity of these compounds toward CT-DNA. This result was also confirmed by the viscosity data. The electrophoresis studies reveal the higher cleavage activity of L1-L3 than L4-L6. The in vitro anti-proliferative activity of these compounds against human colon cancer cell line (HCT 116) revealed that the synthesized compounds (L3, L6 and L2) exhibited good anticancer potency. (C) 2014 Elsevier B.V. All rights reserved.
• Synthesis of nickel(II) complexes of isatin thiosemicarbazone derivatives: <i>in vitro</i> anti-cancer, DNA binding, and cleavage activities
  作者：Amna Qasem Ali、Siang Guan Teoh、Naser Eltaher Eltayeb、Mohamed B. Khadeer Ahamed、Ams Abdul Majid

  DOI：10.1080/00958972.2014.959943

  日期：2014.10.18

  Six new nickel(II) complexes of thiosemicarbazone Schiff base with isatin moiety [Ni(L1)(2)-Ni(L6)(2)] were synthesized through reaction of Ni(II) with (Z)-2-(2-oxoindolin-3-ylidene)-N-phenylhydrazinecarbothioamide (L1H), (Z)-2-(5-methyl-2-oxoindolin-3-ylidene)-N-phenylhydrazinecarbothioamide (L2H), (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)-N-phenylhydrazinecarbothioamide (L3H), (Z)-N-methyl-2-(5-nitro-2-oxoindolin-3-ylidene)hydrazinecarbothioamide (L4H), (Z)-N-methyl-2-(5-methyl-2-oxoindolin-3-ylidene) hydrazinecarbothioamide (L5H), and (Z)-N-ethyl-2-(5-methyl-2-oxo-indolin-3-ylidene) hydrazinecarbothioamide (L6H). The structures of the Ni complexes were characterized through elemental analysis, infrared, and mass spectral data. The structure of the NiL2 complex was further characterized through single-crystal X-ray diffraction. The interaction of these complexes with calf thymus (CT-DNA) exhibited high intrinsic binding constants (K-b = 1.4 x 10(5)-2.4 x 10(6) M-1), which reflected their intercalative activity toward CT-DNA. This result was also confirmed by viscosity data. Electrophoresis studies revealed that these complexes could cleave the DNA through the oxidative pathway. The in vitro anti-proliferative study establishes the anticancer potency of these compounds against human colorectal carcinoma cell line.
• 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.