Synthesis, antibacterial, photostability and molecular docking of novel push–pull dicyanomethylenedihydrofuran chromophores comprising antioxidant moieties

Abstract

Novel push–pull dicyanomethylenedihydrofuran(DCDHF)-based chromophores bearing 6-hydroxyl-2,5,7,8-tetramethylchroman-2-carboxylic acid (HTCX) group were synthesized to function as an antioxidant moiety. The preparation of phenylvinyl-bridged DCDHF chromophores with a hydroxyl functional group to be attached HTCX. Due to intramolecular charge transfer (ICT), HTCX-containing DCDHF chromophores showed a distinct solvatochromism in a range of organic solvents. The molecular structures of the prepared HTCX-bearing DCDHF fluorophores were verified by 1H/13C NMR and FTIR spectroscopic analyses. The emission spectra demonstrated dramatic enhancement in the photostability of the prepared fluorophores. Though, the synthesized HTCX/LSHA(Light Stabilizer Hindered Amine)-DCDHF-based hybrids were studied to evaluated antimicrobial efficiency. HTCX-based hybrid DCDHF-8 revealed sensible activity towards (+ve) Gram and (-ve) Gram bacterial strains, and LSHA-based hybrid DCDHF-15 demonstrated good antibacterial effectiveness against B. cereus (+ve gram) and K. pneumoniae (-ve gram) bactria, comparative to Ampicillin reference. Moreover, the theoretical molecular docking stimulation was realistic to sight see their binding connections towards (PDB-1LNZ).

Keywords

• HTCX-DCDHF chromophores
• antibacterial
• molecular docking
• photostability
• di-hydrofuran