(Z)-2-(5-methyl-2-oxoindolin-3-ylidene)-N-phenylhydrazinecarbothioamide

• 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)-2-(5-methyl-2-oxoindolin-3-ylidene)-N-phenylhydrazinecarbothioamide
• 英文别名: (Z)-2-(5-methyl-2-oxoindolin-3-ylidene)-Nphenylhydrazinecarbothioamide；1-[(5-methyl-2-oxoindol-3-yl)amino]-3-phenylthiourea
• 化学式: C₁₆H₁₄N₄OS
• 分子量: 310.379
• InChiKey: KTWORJQJNNZKMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.64
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  65.52
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  potassium tetrachloroplatinate(II) 、 (Z)-2-(5-methyl-2-oxoindolin-3-ylidene)-N-phenylhydrazinecarbothioamide 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-甲基靛红 、 4-苯基-3-硫代氨基脲 以 乙醇 为溶剂， 反应 2.0h， 以80%的产率得到(Z)-2-(5-methyl-2-oxoindolin-3-ylidene)-N-phenylhydrazinecarbothioamide
  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
• 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.
• Varma, Rajendra S.; Pandey, Rajnish K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 2, p. 157 - 159
  作者：Varma, Rajendra S.、Pandey, Rajnish K.

  DOI：——

  日期：——
• Synthesis of copper(II) complexes of isatin thiosemicarbazone derivatives: In vitro anti-cancer, DNA binding, and cleavage activities
  作者：Amna Qasem Ali、Siang Guan Teoh、Naser Eltaher Eltayeb、Mohamed B. Khadeer Ahamed、A.M.S. Abdul Majid

  DOI：10.1016/j.poly.2014.02.025

  日期：2014.5

  Six new Cu(II) complexes of thiosemicarbazone Schiff base with isatin moiety were synthesized through the reaction of Cu(II) with (Z)-2-(2-oxoindolin-3-ylidene)-N-phenylhydrazinecarbothioamide (CuL1), (Z)-2-(5-methyl-2-oxoindolin-3-ylidene)-N-phenylhydrazinecarbothioamide (CuL2), (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)-N-phenylhydrazinecarbothioamide (CuL3), (Z)-N-methyl-2-(5-nitro-2-oxoindolin-3-ylidene)hydrazinecarbothioamide (CuL4), (Z)-N-methyl-2-(5-methyl-2-oxoindolin-3-ylidene) hydrazinecarbothioamide (CuL5), and (Z)-N-ethyl-2-(5-methy1-2-oxoindolin-3-ylidene)hydrazinecarbothioamide (CuL6). The structures of the Schiff bases and their copper complexes were characterized based on the elemental analysis, and on the infrared, UV-Vis, H-1 and C-13 NMR and ESI-mass spectral data. The structures of the CuL2 and CuL3 complexes were further characterized by single-crystal X-ray diffraction. The interaction of these complexes with calf thymus (CT)-DNA exhibited high intrinsic binding constant (K-b = 1.6 x 10(5)-14.6 x 10(5) M-1), which reflected intercalative activity of these complexes toward CT-DNA. This result was also confirmed by the viscosity data. Electrophoresis studies revealed that the CuL1 and CuL2 complexes were able to cleave the DNA via oxidative pathway, whereas CuL3, CuL4, CuL5, and CuL6 induced DNA cleavage via oxidative and hydrolytic pathways. The in vitro anti-proliferative study establishes the anticancer potency of these compounds against the human colorectal carcinoma cell line. (c) 2014 Elsevier Ltd. All rights reserved.