Coordinated compliance of chloro-methyl and bromo-methyl exchange rule in two dihydrofuran carbonitrile derivatives

Abstract

In the present work, two dihydrofuran carbonitrile derivatives, 2-(4-chlorophenyl)-5-(4-methoxybenzoyl)-4-(4-methylphenyl)-4,5-dihydrofuran-3-carbonitrile and 4-(4-bromophenyl)-5-(4-methoxybenzoyl)-2-(4-methylphenyl)-4,5-dihydrofuran-3-carbonitrile were synthesized and the grown crystals were analyzed based on the X-ray crystallographic data. The title compounds are the first reported instance of compounds which showed a coordinated compliance of two exchange rules viz. the chloro-methyl and bromo-methyl exchange rule. The structures were not only isomorphous but isostructural too, a concept which was further reinforced via the Hirshfeld surface analysis. DFT/B3LYP level of theory employing the 6-311G(d,p) basis set was used to optimize both the compounds. Their global reactivity parameters were assessed based on the HOMO and LUMO values. The drug-likedness were studied by carrying out in silico molecular docking analysis and their binding affinities were compared with the standard drug fluconazole.