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Bioisosterism: Quantitation of Structure and Property Effects
Author(s) -
Kier Lemont B.,
Hall Lowell H.
Publication year - 2004
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.200490006
Subject(s) - chemistry , lone pair , group (periodic table) , polarity (international relations) , sigma , valence electron , bioisostere , computational chemistry , stereochemistry , electron , molecule , organic chemistry , physics , quantum mechanics , biochemistry , chemical synthesis , in vitro , cell
The powerful concept of bioisosterism is presented as a method for selecting molecular groups for drug design and lead‐compound development. Three group‐structure characteristics are described for this purpose. The E‐State value for an attached atom is used as a measure of electrotopological group impact. The volume of the group is estimated from counts of σ , π , and lone‐pair n electrons, as embodied in the valence and simple connectivity δ values for atoms in the group. Polarity is described in terms of the polarity index Q v . Specific examples are given for commonly used groups. Parameter spaces encoding these three attributes are presented as examples that may be used to guide bioisostere selection in late‐stage drug‐design procedures. The method presented here is of practical value in the decision processes of molecular modification.