Inhibition of Hill Reaction by 3-Alcoxyuracil Derivatives: QSAR Study With Topological Indices
نویسنده
چکیده
This study was undertaken to find cl simple and accurate structural parameter for the quantitative description of inhibitory potency of alcoxyuracils in the Hill reaction and to gain more information about the mechanism of inhibition on the molecular level. A very good correlation (1' = 0.987) was obtained between pho values (negative Iogarithm of the concentration that causes 50% inhibition) and the valence first-order and the fifth-order molecular connectivity indices. This model, when compared with the empir ical models based on the n-octanol/water partition coefficients, shows superior or at least comparable performances in accuracy and range of applicability. In addition, the direct correspondence between molecular structure and the above eonnectivity indices make s it possible to locate structural features responsible for the inhibitory potency of alcoxyuracils in the Hill reaction and to learn more about the mechanism of inhibition on the molecular level. From our QSAR analysis, the interaction between the chloroplast receptor site and alcoxyuracils, which cause inhibition of Hill reaction, can he viewed as a two-stage mechanism. The first stage is a complex formation beteween the uracil ring and some active site of chloroplast. The second stage is a hydrophobic interaction between the alcoxy chain and cl hydrophobic region close to the active site. It is assumed that this stage proceeds by the »zippermechanism and that it accounts for the quantitative differences in inhibition found for the studied alcoxyuracils.
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