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Molecules 2011, 16(9), 7893-7908; doi:10.3390/molecules16097893
Article

Studies on Log Po/w of Quinoxaline di-N-Oxides: A Comparison of RP-HPLC Experimental and Predictive Approaches

1,2,*, 2
, 1, 3, 2, 1, 1 and 1
1 Neglected Diseases Section, Drug R&D Unit, Center for Applied Pharmacobiology Research, University of Navarra, C/ Irunlarrea s/n, 31008 Pamplona, Spain 2 Dipartimento di Scienze dell’Ambiente e della Vita, Università del Piemonte Orientale “A. Avogadro”, Viale Michel 11, 15121 Alessandria, Italy 3 School of Chemistry, Cardiff University, Park Place, Cardiff CF10 3AT, UK
* Author to whom correspondence should be addressed.
Received: 30 August 2011 / Revised: 6 September 2011 / Accepted: 7 September 2011 / Published: 13 September 2011
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Abstract

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 Po/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.
Keywords: HPLC; lipophilicity; log P; quinoxalines HPLC; lipophilicity; log P; quinoxalines
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Moreno, E.; Gabano, E.; Torres, E.; Platts, J.A.; Ravera, M.; Aldana, I.; Monge, A.; Pérez-Silanes, S. Studies on Log Po/w of Quinoxaline di-N-Oxides: A Comparison of RP-HPLC Experimental and Predictive Approaches. Molecules 2011, 16, 7893-7908.

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