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Structure-activity correlation study of HIV-1 inhibitors: Electronic and molecular parameters

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Summary

Quantitative structure-activity relationships (QSARs) for 40 HIV-1 inhibitors, 1-[(2-hydroxyethoxy)-methyl]-6-(phenylthio)thymine and its derivatives, were studied. Fully optimized geometries, based on the semiempirical AM1 method, were used to calculate electronic and molecular properties of all compounds. In order to examine the relation between biological activities and structural properties, multiple linear regression models were employed. A suitable QSAR model was obtained, showing not only statistical significance, but also predictive ability. The significant molecular descriptors used were atomic charges of two substituted carbon atoms in the thymine ring, hydration energies and molar refractivities of the molecules. These descriptors allowed a physical explanation of electronic and molecular properties contributing to HIV-1 inhibitory potency.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Kasetsart University, 10900, Bangkok, Thailand

    Supa Hannongbua, Luckhana Lawtrakul & Jumras Limtrakul

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  1. Supa Hannongbua
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  2. Luckhana Lawtrakul
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  3. Jumras Limtrakul
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Hannongbua, S., Lawtrakul, L. & Limtrakul, J. Structure-activity correlation study of HIV-1 inhibitors: Electronic and molecular parameters. J Computer-Aided Mol Des 10, 145–152 (1996). https://doi.org/10.1007/BF00402822

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