Structure-activity relationships for novel drug precursor N-substituted-6-acylbenzothiazolon derivatives: A theoretical approach

In this study, the twelve new modeled N-substituted-6-acylbenzothiazolon derivatives having analgesic analog structure have been investigated by quantum chemical methods using a lot of electronic parameters and structure-activity properties; such as molecular polarizability (alpha), dipole moment (mu), E-HOMO, E-LUMO, q(-), qH(+), molecular volume (V-m), ionization potential (IP), electron affinity (EA), electronegativity (chi), molecular hardness (eta), molecular softness (S), electrophilic index (omega), heat of formation (HOF), molar refractivity (MR), octanol-water partition coefficient (logP), thermochemical properties (entropy (S), capacity of heat (C-v)); as to investigate activity relationships with molecular structure. The correlations of logP with V-m, MR, omega, EA, E-HOMO - E-LUMO (Delta E), HOF in aqueous phase, chi, mu, S, eta parameters, respectively are obtained, while the linear relation of logP with IP, C-v, HOF in gas phase are not observed. The logP parameter is obtained to be depending on different properties of compounds due to their complexity. (C) 2013 Elsevier B.V. All rights reserved.