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. 2011 Sep 13;16(9):7893-908.
doi: 10.3390/molecules16097893.

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

Elsa Moreno  1 , Elisabetta Gabano, Enrique Torres, James A Platts, Mauro Ravera, Ignacio Aldana, Antonio Monge, Silvia Pérez-Silanes
Affiliations

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

Elsa Moreno et al. Molecules. .

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 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.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
General synthetic scheme.
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References

    1. Lima L.M., Barreiro E.J. Bioisosterism: A useful strategy for molecular modification and drug design. Curr. Med. Chem. 2005;12:23–49. doi: 10.2174/0929867053363540. - DOI - PubMed
    1. Carta A., Corona P., Loriga M. Quinoxaline 1,4-dioxide: A versatile scaffold endowed with manifold activities. Curr. Med. Chem. 2005;12:2259–2272. doi: 10.2174/0929867054864831. - DOI - PubMed
    1. Amin K.M., Ismail M.F., Noaman E., Soliman D.H., Ammar Y.A. New quinoxaline 1,4-di-N-oxides. Part 1: Hypoxia-selective cytotoxins and anticancer agents derived from quinoxaline 1,4-di-N-oxides. Bioorg. Med. Chem. 2006;14:6917–6923. - PubMed
    1. Solano B., Junnotula V., Marín A., Villar R., Burguete A., Vicente E., Pérez-Silanes S., Aldana I., Monge A., Dutta S., et al. Synthesis and biological evaluation of new 2-arylcarbonyl-3-trifluoromethylquinoxaline 1,4-di-N-oxide derivatives and their reduced analogs. J. Med. Chem. 2007;50:5485–5492. doi: 10.1021/jm0703993. - DOI - PubMed
    1. Carta A., Loriga M., Paglietti G., Mattana A., Fiori P.L., Mollicotti P., Sechi L., Zanetti S. Synthesis, anti-mycobacterial, anti-trichomonas and anti-candida in vitro activities of 2-substituted-6,7-difluoro-3-methylquinoxaline 1,4-dioxides. Eur. J. Med. Chem. 2004;39:195–203. doi: 10.1016/j.ejmech.2003.11.008. - DOI - PubMed

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