title: QSAR studies of antiviral agents using molecular similarity analysis and structure-activity maps.
abstract: Quantitative structure-activity relationships (QSAR) were developed for nucleoside analogs with anti-HIV activity. These compounds were investigated to determine the correlation of structure and toxicity/activity using molecular similarity analysis and structure-activity maps. A multiple-formula approach was used to perform quantitative molecular similarity analysis (QMSA) and QSAR study. Molecular descriptors such as number of atoms and bonds of a molecule (NAB), maximum common substructure (MaCS), and molecular similarity index (MSI) were used in our structure-activity relationship study. The MaCS of two molecules is defined as the substructure with the greatest NAB value common to both molecules. The MSI of two molecules X and Y is defined as MSI(X,Y) = [MaCS(X,Y)/NAB(X)] x [MaCS(X,Y)/NAB(Y)]. MaCS and MSI quantify the similarity between two molecular structures. Structure-activity maps (structure-toxicity map and structure-antiviral map) and QMSA were used to determine the site and type of modification for reduced toxicity and improved activity of new compounds.
authors.affiliation: Department of Chemistry, Kent State University, Ohio 44242-0001, USA.
authors.forename: R R
authors.initials: RR
authors.lastname: Parakulam
authors.forename: M L
authors.initials: ML
authors.lastname: Lesniewski
authors.forename: K J
authors.initials: KJ
authors.lastname: Taylor-McCabe
authors.forename: C
authors.initials: C
authors.lastname: Tsai
mesh_terms: D019380:Anti-HIV Agents / Q000737:chemistry* / Q000494:pharmacology*; D002460:Cell Line; D002461:Cell Line, Transformed; D016208:Databases, Factual; D006801:Humans; D015394:Molecular Structure; D011741:Pyrimidine Nucleosides / Q000737:chemistry* / Q000494:pharmacology*; D015203:Reproducibility of Results; D013329:Structure-Activity Relationship
chemical_list: D019380:Anti-HIV Agents; D011741:Pyrimidine Nucleosides