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Molecules 2013, 18(8), 9061-9116; doi:10.3390/molecules18089061

Determining Chemical Reactivity Driving Biological Activity from SMILES Transformations: The Bonding Mechanism of Anti-HIV Pyrimidines

Laboratory of Computational and Structural Physical Chemistry for Nanosciences and QSAR, Biology-Chemistry Department, West University of Timişoara, Pestalozzi Str. No. 16, Timişoara 300115, Romania
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Received: 30 May 2013 / Revised: 22 July 2013 / Accepted: 24 July 2013 / Published: 30 July 2013
(This article belongs to the Special Issue Computational Chemistry)
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Abstract

Assessing the molecular mechanism of a chemical-biological interaction and bonding stands as the ultimate goal of any modern quantitative structure-activity relationship (QSAR) study. To this end the present work employs the main chemical reactivity structural descriptors (electronegativity, chemical hardness, chemical power, electrophilicity) to unfold the variational QSAR though their min-max correspondence principles as applied to the Simplified Molecular Input Line Entry System (SMILES) transformation of selected uracil derivatives with anti-HIV potential with the aim of establishing the main stages whereby the given compounds may inhibit HIV infection. The bonding can be completely described by explicitly considering by means of basic indices and chemical reactivity principles two forms of SMILES structures of the pyrimidines, the Longest SMILES Molecular Chain (LoSMoC) and the Branching SMILES (BraS), respectively, as the effective forms involved in the anti-HIV activity mechanism and according to the present work, also necessary intermediates in molecular pathways targeting/docking biological sites of interest. View Full-Text
Keywords: anti-HIV activity; 1,3-disubstituted uracil derivatives; QSAR; SMILES; electronegativity; chemical hardness; chemical power; electrophilicity; chemical reactivity principles; lipophilicity anti-HIV activity; 1,3-disubstituted uracil derivatives; QSAR; SMILES; electronegativity; chemical hardness; chemical power; electrophilicity; chemical reactivity principles; lipophilicity
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Putz, M.V.; Dudaş, N.A. Determining Chemical Reactivity Driving Biological Activity from SMILES Transformations: The Bonding Mechanism of Anti-HIV Pyrimidines. Molecules 2013, 18, 9061-9116.

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