TY - JOUR
T1 - Novel approach for the numerical characterization of molecular chirality
AU - Natarajan, Ramanathan
AU - Basak, Subhash C
AU - Neumann, Terrence S.
PY - 2007/5
Y1 - 2007/5
N2 - The use of chiral compounds as pharmaceuticals and agrochemicals continues to increase, warranting numerical characterization of chirality in order to develop structure-activity relationship models involving these compounds. Enantiomers are identical in all scalar properties and, hence, are not differentiated by topological indices and 3-D descriptors. Three distinct measures of chirality were developed to discriminate diastereomers and enantiomers. The novel topological indices treat chirality as a continuous measure, and hence we prefer to call it the Relative Chirality Index (RCI). Application of RCI in developing SAR is illustrated with the repellency data for the diastereomers of picaridin and AI3-37220.
AB - The use of chiral compounds as pharmaceuticals and agrochemicals continues to increase, warranting numerical characterization of chirality in order to develop structure-activity relationship models involving these compounds. Enantiomers are identical in all scalar properties and, hence, are not differentiated by topological indices and 3-D descriptors. Three distinct measures of chirality were developed to discriminate diastereomers and enantiomers. The novel topological indices treat chirality as a continuous measure, and hence we prefer to call it the Relative Chirality Index (RCI). Application of RCI in developing SAR is illustrated with the repellency data for the diastereomers of picaridin and AI3-37220.
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U2 - 10.1021/ci600542b
DO - 10.1021/ci600542b
M3 - Article
C2 - 17408241
AN - SCOPUS:34250856929
SN - 1549-9596
VL - 47
SP - 771
EP - 775
JO - Journal of Chemical Information and Modeling
JF - Journal of Chemical Information and Modeling
IS - 3
ER -