Structure-Activity Relationship of the Antifungal  1-Aryl-2-(azol-1-yl)ethane Derivatives

Bélai, I. and Oros, G. (2006) Structure-Activity Relationship of the Antifungal  1-Aryl-2-(azol-1-yl)ethane Derivatives. Acta Phytopathologica et Entomologica Hungarica, 41 (1-2). pp. 109-119. ISSN 0238-1249

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Abstract

The relationship between the chemical structure of 54 1-aryl-2-(azol-1-yl)ethane derivatives and their antifungal activities, tested on 30 fungal species, have been examined. Among the 1-keto derivatives the compounds with a longer alkyl chain at the carbon atom adjacent to the azole ring as well as the chloro substituent on the benzene ring showed the highest antifungal activity, meanwhile, a shorter chain at the same carbon atom led to highest activity among the 1-chloro derivatives. To find the physico-chemical properties influencing the antifungal activity two series of molecular descriptors have been calculated applying the Dragon and the Sybyl VolSurf computer programs. The 3D structures of the compounds to these calculations were generated with the HYPERCHEM and the SYBYL molecular modeling programs. From the equation, obtained with stepwise regression using the antifungal activity data as dependent and the descriptors as independent variables, it is obvious that the factors describing the chemical structure itself (Dragon descriptors) have greater influence on the antifungal activity than the factors responsible for the passive penetration (VolSurf descriptors). The principal component analysis revealed that the 1-chloro derivatives, which are equipotent or more potent than the 10 reference azole fungicides, have at least two action modes.

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