Steric Fit in Quantitative Structure-Activity Relations

Comparative Study of Lipophilicity versus Topological Molecular Descriptors in Biological Correlations

“…In contemporary biomcdicinal chemistry, quantum chemical ( 1 -4), physicochemical (5)(6)(7), and topological (8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21) parameters have been extensively utilized in the prediction of biological activity of molecules. While quantum chemical descriptors provide the most accurate numerical information regarding molecular architecture, the complexity of many bioactive molecules precludes the possibility of the extensive use of these methods in drug design (8).…”

“…In particular, QSAR literature of recent years shows the progressive reliance on various topological indices as convenient structural parameters for correlational studies in chemistry (8,30) and biology (8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21). Although a topological index is likely to be inherently steric in nature by virtue of being a numerical descriptor of molecular shape and size (8,21), the most important progress in this area has been the development of topological structural parameters capable of expressing the electronic properties of molecules (3 1, 32). One of the necessary preconditions of successful QSAR analysis is the availability of a set of parameters with minimum overlap profile (21,33).…”

“…Although a topological index is likely to be inherently steric in nature by virtue of being a numerical descriptor of molecular shape and size (8,21), the most important progress in this area has been the development of topological structural parameters capable of expressing the electronic properties of molecules (3 1, 32). One of the necessary preconditions of successful QSAR analysis is the availability of a set of parameters with minimum overlap profile (21,33). Therefore, it seemed fitting to study the relative efficacies of lipophilicity u i s -h i s steric descriptors in rationalizing pharmacological and toxicological properties.…”

Influence of the Energy Relationships of Organic Compounds on Toxicity to the CladoceranDaphnia magnaand the FishPimephales promelas

“…It may be an illustration of the often stated principle that the larger-scale pattern (in this case, across classes) and the smaller scale pattern (in this case, within classes) are complementary perspectives and that they may be different. Here the broader pattern may be dominated by factors such as rarity and complexity, whereas factors such as the chemical reactivity (steric crowding of chlorine atoms) and the physicochemical properties (tendency to sorb to lipids) (Balaban et al, 1980) may prevail within a class of compounds and modify the relationship between transformity and toxicity. Earlier studies have pointed to a similar conclusion.…”

Mean-field resonance-theoretic view of benzenoid networks

“…• the development and application of various "topological indices" for QSAR and QSPR methods 1,2,3 ;…”