title: Similarity approach to QSAR. Application to antimycobacterial benzoxazines.
abstract: The antimycobacterial activity in six series of substituted 3-phenyl-2H-benzoxazine-2,4(3H)-dithiones and 3-(phenyl)-4-thioxo-2H-benzoxazine-2,4(3H)-diones has been studied using a quantum molecular similarity approach. The approach is based on the use of fragment self-similarity measures as new universal molecular descriptors applicable for the design of novel theoretical QSAR models. Using this approach it was possible to show that while traditional QSAR models were able to describe the activity only within each of the six sets of studied molecules individually, the proposed approach is much more general and a single universal QSAR model describing the activity of all the 39 studied molecules in all the studied series together was built. The replacement of the oxo group by the thioxo group in position 4 on the benzoxazine ring of the antitubercular 3-(phenyl)-2H-benzoxazine-2,4(3H)-diones increases the activity, as well as the similar replacement in position 2.
authors.affiliation: Institute of Computational Chemistry, University of Girona, Campus Montilivi 17071, Girona, Spain
authors.forename: Ana
authors.initials: A
authors.lastname: Gallegos
authors.forename: Ramon
authors.initials: R
authors.lastname: Carbó-Dorca
authors.forename: Robert
authors.initials: R
authors.lastname: Ponec
authors.forename: Karel
authors.initials: K
authors.lastname: Waisser
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry*; D000995:Antitubercular Agents / Q000737:chemistry*; D008958:Models, Molecular; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D010078:Oxazines / Q000737:chemistry*; D021281:Quantitative Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; D000995:Antitubercular Agents; D010078:Oxazines