title: Quantitative structure-activity relationship studies for the prediction of antifungal activity of N-arylbenzenesulfonamides against Botrytis cinerea.
abstract: The Botrytis cinerea is one of the most interesting fungal pathogens. It can infect almost every plant and plant part and cause early latent infections which damage the fruit before ripening. The QSAR is an alternative method for the research of new and better fungicides against B. cinerea. This paper describes the results of applying a topological sub-structural molecular design (TOPS-MODE) approach for predicting the antifungal activity of 28 N-arylbenzenesulfonamides. The model described 86.1% of the experimental variance, with a standard deviation of 0.223. Leave-one-out and leave-group-out cross validation was carried out with the aim of evaluating the predictive power of the model. The values of their respective squared correlations coefficients were 0.754 and 0.741. The TOPS-MODE approach was compared with three other predictive models, but none of these could explain more than 72.8% of the variance with the same number of variables. In addition, this approach enabled the assessment of the contribution of different bonds to antifungal activity, thereby making the relationships between structure and biological activity more transparent. It was found that the fungicidal activity of the chemicals analyzed was increased by the presence of a sulfonamide group bonded to two aromatics rings, making this group the most important of the molecule. The majority of the substituents present in the aromatic rings have an electron withdrawing effect and they contribute to a smaller degree than the sulfonamide group to the property under study. The aromatic moiety plays an important role in this activity; its contribution changes with different substituents. Generally, the nitro group has a positive and great contribution to the biological property but when this group is involved in some compounds in ortho effect with the SO2 moiety of the sulfonamide group a lower value of contribution is observed for both groups.
authors.affiliation: Chemical Bioactive Center, Central University of Las Villas, Santa Clara, Villa Clara, C.P. 54830, Cuba.
authors.forename: Liane
authors.initials: L
authors.lastname: Saíz-Urra
authors.forename: Maykel Pérez
authors.initials: MP
authors.lastname: González
authors.forename: Isidro G
authors.initials: IG
authors.lastname: Collado
authors.forename: Rosario
authors.initials: R
authors.lastname: Hernández-Galán
mesh_terms: D020171:Botrytis / Q000187:drug effects*; D003196:Computer Graphics; D003198:Computer Simulation; D005659:Fungicides, Industrial / Q000737:chemistry* / Q000494:pharmacology*; D008956:Models, Chemical; D008958:Models, Molecular; D021281:Quantitative Structure-Activity Relationship; D013449:Sulfonamides / Q000737:chemistry* / Q000494:pharmacology*
chemical_list: D005659:Fungicides, Industrial; D013449:Sulfonamides