Study of the Chemical Space of Selected Bacteriostatic Sulfonamides from an Information Theory Point of View

• Published in: Chemphyschem 2016-12, Vol.17 (23), p.4003-4010
• Main Authors: López-Rosa, Sheila, Molina-Espíritu, Moyocoyani, Esquivel, Rodolfo O., Soriano-Correa, Catalina, Dehesa, Jésus S.
• Format: Article
• Language: English
• Subjects: chemical space; electronic structure; Information theory; structure-activity relationships; sulfonamides
• ISSN: 1439-4235; 1439-7641
• DOI: 10.1002/cphc.201600790

The relative structural location of a selected group of 27 sulfonamide‐like molecules in a chemical space defined by three information theory quantities (Shannon entropy, Fisher information, and disequilibrium) is discussed. This group is composed of 15 active bacteriostatic molecules, 11 theoretically designed ones, and para‐aminobenzoic acid. This endeavor allows molecules that share common chemical properties through the molecular backbone, but with significant differences in the identity of the chemical substituents, which might result in bacteriostatic activity, to be structurally classified and characterized. This is performed by quantifying the structural changes on the electron density distribution due to different functional groups and number of electrons. The macroscopic molecular features are described by means of the entropy‐like notions of spatial electronic delocalization, order, and uniformity. Hence, an information theory three‐dimensional space (IT‐3D) emerges that allows molecules with common properties to be gathered. This space witnesses the biological activity of the sulfonamides. Some structural aspects and information theory properties can be associated, as a result of the IT‐3D chemical space, with the bacteriostatic activity of these molecules. Most interesting is that the active bacteriostatic molecules are more similar to para‐aminobenzoic acid than to the theoretically designed analogues. Hunt and gather: The relative structural location of a selected group of 27 sulfonamide‐like molecules in the framework of a chemical space defined by three information theory quantities (Shannon entropy, Fisher information, and disequilibrium) is described. An information theory 3D space (IT‐3D) emerges that allows molecules with common properties to be gathered (see figure; PABA= para‐aminobenzoic acid).