Spectroscopic (FTIR, UV–Vis and NMR), theoretical investigation and molecular docking of substituted 1,8-dioxodecahydroacridine derivatives

Abstract

Recently, substituted 1,8-dioxodecahydroacridine derivatives have been investigated and found to possess a wide variety of biological and phar­macological activities. Two of these biologically relevant N-heterocyclic scaf­folds, 2-(9-(4-me­th­oxyphenyl)-3,3,6,6-tetramethyl-1,8-dioxo-1,2,3,4,5,6,7,8-oc­ta­hydroacridin-10(9H)-yl)succinic acid (MTDOSA) and 2-(3,3,6,6-tetra­methyl-9-(4-nitrophenyl)-1,8-dioxo-1,2,3,4,5,6,7,8-octahydroacridin-10(9H)-yl)­suc­ci­nic acid (NTDOSA), have been studied in ground and first excited state using DFT method employing B3LYP/6-311++G(d,p) level of theory. Quan­tum che­mical calculations of geometrical structure and vibrational wave­numbers of MTDOSA and NTDOSA were carried out using DFT method. The expe­ri­men­tal FT-IR spectra of the compounds were recorded in the range 4000–400 cm-1 and comprehensively interpreted on the basis of potential energy distribution. The global reactivity descriptors are calculated and discussed. Moreover, 1H- and 13C-NMR spectral data have been calculated using the gauge independent atomic orbital method and compared with experimental spectra. The docking studies reveal that the compounds MTDOSA and NTDOSA have strong binding affinity toward the target protein 5KLH. Thus, the compounds have a possible use as an antileishmanial drug.