N-cyclohexyl-2-(5-methoxy-2-oxoindolin-3-ylidene)hydrazinecarbothioamide | 1204740-42-0

• 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: N-cyclohexyl-2-(5-methoxy-2-oxoindolin-3-ylidene)hydrazinecarbothioamide
• 英文别名: 5-methoxyisatin-3-(N-cyclohexyl)thiosemicarbazone；1-cyclohexyl-3-[(5-methoxy-2-oxoindol-3-yl)amino]thiourea
• CAS: 1204740-42-0
• 化学式: C₁₆H₂₀N₄O₂S
• 分子量: 332.426
• InChiKey: KTDJBAJSHQEHKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  74.75
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-cyclohexyl-2-(5-methoxy-2-oxoindolin-3-ylidene)hydrazinecarbothioamide 、 zinc diacetate 以 乙醇 为溶剂， 以80%的产率得到bis(5-methoxyisatin-3-(N-cyclohexyl)thiosemicarbazonato)zinc(II) hydrate
  参考文献：
  名称：

  Synthesis and theoretical study of 5-methoxyisatin-3-(N-cyclohexyl)thiosemicarbazone and its Ni(II) and Zn(II) complexes

  摘要：

  5-Methoxyisatin-3-(N-cyclohexyl)thiosemicarbazone (H2MICT) and its Zn(II) and Ni(II) complexes have been synthesized and characterized using IR, H-1 NMR, C-13-NMR, MS, UV and elemental analysis. (H2MICT) ligand has been characterized with X-ray diffraction method also The possible structures and IR data of the studied molecules were Calculated and compared with experimental results using B3LYP/6-31G(d,p) and B3LYP/LANL2DZ methods. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2009.09.009
• 作为产物：
  描述：

  5-甲氧基靛红 、 4-环己基-3-硫代氨基脲 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以83%的产率得到N-cyclohexyl-2-(5-methoxy-2-oxoindolin-3-ylidene)hydrazinecarbothioamide
  参考文献：
  名称：

  Synthesis and characterisations of copper(II) complexes of 5-methoxyisatin thiosemicarbazones: Effect of N-terminal substitution on DNA/protein binding and biological activities

  摘要：

  The newly synthesized ligands (HL1-HL3) of 5-methoxyisatin thiosemicarbazone with different N-terminal substituents and their copper(II) complexes 1-3 respectively were exposed to spectral and structural characterization. The spectral studies reveal that the ligands show a tridentate mode of binding (ONS donor) with Cu (II) to form square planar complexes. The crystal structure of the ligand HL1 and complex 1 were confirmed by single crystal XRD. The compounds were subjected to DNA/BSA interaction studies using electronic and fluorescence spectroscopic techniques. The binding studies showed that, the complexes (1-3) were able to bind with DNA/BSA macromolecules with good binding constant. In which 1 (K-b = 0.83 x 10(5) M-1) shows good interaction with the DNA while 3 shows better interaction with BSA (K-b = 2.4 x 10(5) M-1). The complexes (1-3) were also tested for antimicrobial activity, radical scavenging activity and in vitro anti-proliferative activity. Complex 3 have shown potent efficacy with broad spectrum antimicrobial activity against the microorganisms, whereas the complex 1 has shown decent scavenging properties compared to the reference drug (ascorbic acid) with an IC50 value of 19.23 +/- 1.05 mu M. Further the, anti-proliferative activity study revealed that, the complex 1 has exhibited broad spectrum activity against MCF-7, A549 and HeLa with IC50 values 14.83 +/- 0.45 mu M, 17.88 +/- 0.16 mu M and 6.89 +/- 0.42 mu M, respectively compared to standard drug Doxorubicin.

  DOI：

  10.1016/j.ica.2019.04.019

文献信息

• Synthesis and characterisations of copper(II) complexes of 5-methoxyisatin thiosemicarbazones: Effect of N-terminal substitution on DNA/protein binding and biological activities
  作者：K.N. Aneesrahman、K. Ramaiah、G. Rohini、G.P. Stefy、N.S.P. Bhuvanesh、A. Sreekanth

  DOI：10.1016/j.ica.2019.04.019

  日期：2019.6

  The newly synthesized ligands (HL1-HL3) of 5-methoxyisatin thiosemicarbazone with different N-terminal substituents and their copper(II) complexes 1-3 respectively were exposed to spectral and structural characterization. The spectral studies reveal that the ligands show a tridentate mode of binding (ONS donor) with Cu (II) to form square planar complexes. The crystal structure of the ligand HL1 and complex 1 were confirmed by single crystal XRD. The compounds were subjected to DNA/BSA interaction studies using electronic and fluorescence spectroscopic techniques. The binding studies showed that, the complexes (1-3) were able to bind with DNA/BSA macromolecules with good binding constant. In which 1 (K-b = 0.83 x 10(5) M-1) shows good interaction with the DNA while 3 shows better interaction with BSA (K-b = 2.4 x 10(5) M-1). The complexes (1-3) were also tested for antimicrobial activity, radical scavenging activity and in vitro anti-proliferative activity. Complex 3 have shown potent efficacy with broad spectrum antimicrobial activity against the microorganisms, whereas the complex 1 has shown decent scavenging properties compared to the reference drug (ascorbic acid) with an IC50 value of 19.23 +/- 1.05 mu M. Further the, anti-proliferative activity study revealed that, the complex 1 has exhibited broad spectrum activity against MCF-7, A549 and HeLa with IC50 values 14.83 +/- 0.45 mu M, 17.88 +/- 0.16 mu M and 6.89 +/- 0.42 mu M, respectively compared to standard drug Doxorubicin.
• Synthesis and theoretical study of 5-methoxyisatin-3-(N-cyclohexyl)thiosemicarbazone and its Ni(II) and Zn(II) complexes
  作者：Fatma Kandemirli、Taner Arslan、Nevzat Karadayı、Eno.E. Ebenso、Baybars Köksoy

  DOI：10.1016/j.molstruc.2009.09.009

  日期：2009.12

  5-Methoxyisatin-3-(N-cyclohexyl)thiosemicarbazone (H2MICT) and its Zn(II) and Ni(II) complexes have been synthesized and characterized using IR, H-1 NMR, C-13-NMR, MS, UV and elemental analysis. (H2MICT) ligand has been characterized with X-ray diffraction method also The possible structures and IR data of the studied molecules were Calculated and compared with experimental results using B3LYP/6-31G(d,p) and B3LYP/LANL2DZ methods. (C) 2009 Elsevier B.V. All rights reserved.