Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 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.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Scheme 1
Scheme 1
General synthetic scheme.
See this image and copyright information in PMC

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

Publication types

MeSH terms