Chirality Factors and Their Application to QSAR Studies of Chiral Molecules
Chunsheng Yang, Chongli Zhong · QSAR & Combinatorial Science · 2005
Abstract Two series of chirality factors that can distinguish enantiomers and diastereomers were developed in this work and the corresponding chiral topological indices were proposed. The obtained chiral topological indices can be used to perform QSAR studies for chiral molecules. The biological activities of fourteen 3‐(3‐hydroxyphenyl)‐ piperidines (seven pairs of enantiomers), the high‐pressure thin‐layer chromatographic retention indices of eight hydroxy acids and ten amino acids (nine pairs of enantiomers), the ED50 of 23 ecdysteroids (19 pairs of diastereomers), and the corticosteroid‐binding globulins affinities of 31 steroids were used to evaluate the chirality factors and the corresponding chiral topological indices. The QSAR models developed give satisfactory predictive accuracy. Compared with the existing methods, the chirality factor method proposed in this work has the advantage of being applicable to the existing topological indices directly. This makes good use of the existing topological indices, and thus brings convenience to the QSAR studies for chiral molecules. Another advantage of the new method is that it can also correctly describe the characteristics of meso compounds.