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

Disclosure statement

No potential conflict of interest was reported by the author(s).

Availability of data and materials

All relevant data are within the manuscript and available from the corresponding author upon request.