Characterization, phase-solubility, and molecular modeling of inclusion complex of 5-nitroindazole derivative with cyclodextrins

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• 作者：Carolina Jullian ; Javier Morales-Montecinos ; Gerald Zapata-Torres ; Benjamí ; n Aguilera ; Jorge Rodriguez ; Vicente Ará ; n ; Claudio Olea-Azar
• 关键词：5-Nitroindazole ; Cyclodextrin ; NMR ; Molecular modeling ; Electrochemistry
• 刊名：Bioorganic and Medicinal Chemistry
• 出版年：2008
• 期刊代码：9_09680896
• 类别：ch
• 出版时间：1 May 2008
• 卷：16
• 期：9
• 页码：5078-5084
• 文件大小：469 K

摘要

The slightly water-soluble 5-nitroindazole derivative (5-NI) and its inclusion with either β-cyclodextrin (βCD) or Heptakis (2,6-di-O-methyl)-β-cyclodextrin (DMβCD) were investigated. The stoichiometric ratios and stability constants describing the extent of formation of the complexes were determined by phase-solubility measurements obtaining type-A_L diagrams in both cases. According to the continuous variation method (Job’s plot) a 1:1 stoichiometry has been proposed for the complexes. Also electrochemical studies were carried out on both CDs complexes, where the observed change in the E_PC value for DMβCD indicated a lower feasibility of the nitro group reduction. The detailed spatial configuration is proposed based on two-dimensional NMR methods. These results are further interpreted using molecular modeling studies. The latter results are in good agreement with the experimental data.