Studies on log Po/w of quinoxaline di-N-oxides: a comparison of RP-HPLC experimental and predictive approaches

As reported in our previous papers, a series of quinoxaline-2-carboxamide 1,4-di-N-oxide derivatives were synthesized and studied as anti-tuberculosis agents. Here, the capability of the shake-flask method was studied and the retention time (expressed as log K) of 20 compounds were determined by RP-...

Full description

Saved in:
Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2011-09, Vol.16 (9), p.7893-7908
Main Authors: Moreno, Elsa, Gabano, Elisabetta, Torres, Enrique, Platts, James A, Ravera, Mauro, Aldana, Ignacio, Monge, Antonio, Pérez-Silanes, Silvia
Format: Article
Language:English
Subjects:
Chromatography
Chromatography, High Pressure Liquid
Cyclic N-Oxides - analysis
Cyclic N-Oxides - chemical synthesis
Cyclic N-Oxides - pharmacology
HPLC
lipophilicity
log P
Methods
Microbial Sensitivity Tests
Mycobacterium tuberculosis - drug effects
Pharmaceutical sciences
Quantitative Structure-Activity Relationship
Quinolines - analysis
Quinolines - chemical synthesis
Quinolines - pharmacology
quinoxalines
Quinoxalines - chemical synthesis
Quinoxalines - chemistry
Quinoxalines - pharmacology
Tuberculosis
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:As reported in our previous papers, a series of quinoxaline-2-carboxamide 1,4-di-N-oxide derivatives were synthesized and studied as anti-tuberculosis agents. Here, the capability of the shake-flask method was studied and the retention time (expressed as log K) of 20 compounds were determined by RP-HPLC analysis. We found that the prediction of log P by the RP-HPLC analysis can result in a high accuracy and can replace the shake-flask method avoiding the experimental problems presented by quinoxaline di-N-oxides. The studied compounds were subjected to the ALOGPS module with the aim of comparing experimental log P(o/w) values and predicted data. Moreover, a preliminary in silico screening of the QSAR relationship was made confirming the influence of reduction peak potential, lipophilicity, H-bond donor capacity and molecular dimension descriptors on anti-tuberculosis activity.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules16097893