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Studies on Log Po/w of Quinoxaline di-N-Oxides: A Comparison of RP-HPLC Experimental and Predictive Approaches
Neglected Diseases Section, Drug R&D Unit, Center for Applied Pharmacobiology Research, University of Navarra, C/ Irunlarrea s/n, 31008 Pamplona, Spain
Dipartimento di Scienze dell’Ambiente e della Vita, Università del Piemonte Orientale “A. Avogadro”, Viale Michel 11, 15121 Alessandria, Italy
School of Chemistry, Cardiff University, Park Place, Cardiff CF10 3AT, UK
* Author to whom correspondence should be addressed.
Received: 30 August 2011; in revised form: 6 September 2011 / Accepted: 7 September 2011 / Published: 13 September 2011
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
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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.
Moreno E, Gabano E, Torres E, Platts JA, 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(9):7893-7908.
Moreno, Elsa; Gabano, Elisabetta; Torres, Enrique; Platts, James A.; Ravera, Mauro; Aldana, Ignacio; Monge, Antonio; Pérez-Silanes, Silvia. 2011. "Studies on Log Po/w of Quinoxaline di-N-Oxides: A Comparison of RP-HPLC Experimental and Predictive Approaches." Molecules 16, no. 9: 7893-7908.