QSAR study on antibacterial and antifungal activities of some 3,4-disubstituted-1,2,4-oxa(thia)-diazole-5(4 H)-ones(thiones) using physicochemical, quantumchemical and structural parameters
O. Geban et al., QSAR study on antibacterial and antifungal activities of some 3,4-disubstituted-1,2,4-oxa(thia)-diazole-5(4 H)-ones(thiones) using physicochemical, quantumchemical and structural parameters, EUR J MED C, 34(9), 1999, pp. 753-758
This work demonstrated the quantitative structure-activity relationships of
3,4-disubstituted-1,2,4-oxa(thia)-diazole-5(4 H)-ones (thiones) using quan
tum chemical parameter R(I), hydrophobicity descriptor and structural param
eters. Semiempirical molecular orbital calculations were used to determine
the quantum chemical parameter R(I), which is the electron density of HOMO
at the sulfur and oxygen in position 1 of the compounds investigated, divid
ed by the orbital energy of HOMO. It was shown that the electron density of
HOMO at the sulfur and oxygen of the molecules was strongly related to the
biological activities of these molecules. The results obtained from the QS
AR application indicated that there was a parabolic dependence between the
biological activities and the R(I) index. The structural factor I-Y which s
hows the presence of a sulfur atom in position 1 was the dominant predictor
for the antibacterial and antifungal activities. On the other hand, the ot
her structural variable I-X which shows the presence of a sulfur atom doubl
e bonded to the C atom in position 5 caused a decrease, but the hydrophobic
ity of the whole molecule (Sigma) caused an increase in activity. (C) 1999
Editions scientifiques et medicales Elsevier SAS.