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

Jullian C.; Morales-Montecinos, J; Zapata-Torres, G; Aguilera B.; Rodriguez J.; Aran, V; Olea Azar C.

Abstract

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. © 2008 Elsevier Ltd. All rights reserved.

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Título según WOS: Characterization, phase-solubility, and molecular modeling of inclusion complex of 5-nitroindazole derivative with cyclodextrins
Título según SCOPUS: Characterization, phase-solubility, and molecular modeling of inclusion complex of 5-nitroindazole derivative with cyclodextrins
Título de la Revista: BIOORGANIC & MEDICINAL CHEMISTRY
Volumen: 16
Número: 9
Editorial: PERGAMON-ELSEVIER SCIENCE LTD
Fecha de publicación: 2008
Página de inicio: 5078
Página final: 5084
Idioma: English
DOI:

10.1016/j.bmc.2008.03.026

Notas: ISI, SCOPUS