Molecular encapsulation of 5-nitroindazole derivatives in 2,6-dimethyl-beta-cyclodextrin: electrochemical and spectroscopic studies.

Bioorg Med Chem

Departamento de Química Orgánica y Fisicoquímica, Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Casilla 233, Santiago 1, Chile.

Published: July 2009

AI Article Synopsis

Article Abstract

Four different 5-nitroindazole derivatives (1-4) and its inclusion with Heptakis(2,6-di-O-methyl)-beta-cyclodextrin (DMbetaCD) were investigated. The stoichiometric ratios and stability constants describing the extent of formation of the complexes were determined by phase-solubility measurements obtaining in all cases a type-A(L) diagram. Also electrochemical studies were carried out, where the observed change in the E(PC) value indicated a lower feasibility of the nitro group reduction. The same behavior was observed in the ESR studies. The detailed spatial configuration is proposed based on 2D NMR methods. These results are further interpreted using molecular modeling studies. The latter results are in good agreement with the experimental data.

Download full-text PDF

Source
http://dx.doi.org/10.1016/j.bmc.2009.04.067DOI Listing

Publication Analysis

Top Keywords

5-nitroindazole derivatives
8
molecular encapsulation
4
encapsulation 5-nitroindazole
4
derivatives 26-dimethyl-beta-cyclodextrin
4
26-dimethyl-beta-cyclodextrin electrochemical
4
electrochemical spectroscopic
4
studies
4
spectroscopic studies
4
studies 5-nitroindazole
4
derivatives 1-4
4

Similar Publications

3-Alkoxy-1-Benzyl-5-Nitroindazole Derivatives Are Potent Antileishmanial Compounds.

Int J Mol Sci

October 2024

Instituto de Química Médica del Consejo Superior de Investigaciones Científicas de España, Juan de la Cierva 3, 28006 Madrid, Spain.

Indazoles have previously been identified as molecules with antiprotozoal activity. In this study, we evaluate the in vitro activity of thirteen 3-alkoxy-1-benzyl-5-nitroindazole derivatives (series D) against , and . In vitro, cytotoxicity against mouse peritoneal macrophages and growth inhibitory activity in promastigotes were evaluated for all compounds, and those showing adequate activity and selectivity were tested against intracellular amastigotes.

View Article and Find Full Text PDF

Antileishmanial activity of 5-nitroindazole derivatives.

Ther Adv Infect Dis

October 2023

Instituto de Química Médica del Consejo Superior de Investigaciones Científicas de España, Madrid, España.

Background: Currently, there is no safe and effective vaccine against leishmaniasis and existing therapies are inadequate due to high toxicity, cost and decreased efficacy caused by the emergence of resistant parasite strains. Some indazole derivatives have shown and activity against and . On that basis, 20 indazole derivatives were tested against .

View Article and Find Full Text PDF

5-Nitroindazole-based compounds: further studies for activity optimization as anti-Trypanosoma cruzi agents.

Acta Trop

October 2022

Instituto de Química Médica (IQM), Consejo Superior de Investigaciones Científicas (CSIC), c/ Juan de la Cierva 3, 2006, Madrid, Spain.

In this study, a new series of eleven 5-nitroindazole derivatives (10-20) and a related 6-nitroquinazoline (21) was synthesized and tested in vitro against different forms of the kinetoplastid parasite Trypanosoma cruzi, etiological agent of Chagas disease. Among these compounds, derivatives 11-14 and 17 showed trypanocidal profiles on epimastigotes (IC = 1.00-8.

View Article and Find Full Text PDF

Amoebas of the genus Acanthamoeba are distributed worldwide, including species with a high pathogenic capacity for humans. In a similar way to what occurs with other parasitic protozoa, the available treatments show variable effectiveness in addition to high toxicity, which demands the development of new treatments. Positive results of 5-nitroindazole derivatives against several protozoa parasites suggest that these compounds may be a promising tool for the development of efficient antiparasitic drugs.

View Article and Find Full Text PDF

Activity profile of two 5-nitroindazole derivatives over the moderately drug-resistant Y strain (DTU TcII): and studies.

Parasitology

September 2020

Laboratório de Biologia Celular, Instituto Oswaldo Cruz, Fundação Oswaldo Cruz (FIOCRUZ), Av. Brasil 4365, 21040-900Rio de Janeiro, Brazil.

In previous studies, we have identified several families of 5-nitroindazole derivatives as promising antichagasic prototypes. Among them, 1-(2-aminoethyl)-2-benzyl-5-nitro-1,2-dihydro-3H-indazol-3-one, (hydrochloride) and 1-(2-acetoxyethyl)-2-benzyl-5-nitro-1,2-dihydro-3H-indazol-3-one (compounds 16 and 24, respectively) have recently shown outstanding activity in vitro over the drug-sensitive Trypanosoma cruzi CL strain (DTU TcVI). Here, we explored the activity of these derivatives against the moderately drug-resistant Y strain (DTU TcII), in vitro and in vivo.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!