Synthesis, computational and molecular docking study of some 2, 3-dihydrobenzofuran and its derivatives

• A new series of 2, 3-dihydrobenzofuran derivatives were synthesized. • Their chemical structure and their conversion in synthesis were confirmed by the spectral data obtained from the FTIR, 1 H NMR and 13 C NMR. • 2, 3-Dihydrobenzofuran and its derivatives were found to be the antifungal and antibacterial activity against two fungi and one bacteria by molecular docking. • Alkyl chain in 3 position of benzofuran showed the effect on biological activity. • Chemical stability and chemical reactivity were optimized by DFT. 2, 3-Dihydrobenzofuran-2-carboxylates (DHBC) derivatives were synthesized by cyclization on one pot reaction, and characterized by FT-IR, 1H NMR and 13 C NMR spectral studies. The intermolecular coupling reactions of 2-iodophenols with acrylic esters by the Pd(Ph 3 P) 2 Cl 2 catalyst were investigated. The density functional theory (DFT) calculations have been executed for the DHBC using B3LYP/6–31++G (d, p) and B3LYP/6–31++G (d, p) for obtaining HOMO and LUMO, descriptors, vibrational properties and charge distribution potential. The HOMO-LUMO gap were found to be 0.23450, 0.20104, 0.20711, 0.16533, 0.29371 and -0.32549 eV for 6–11 DHBC, respectively. The calculated IR and NMR are correlated with experimental value. Molecular docking studies predict the microbial activity of DHBC against both fungi and bacteria calculating the binding energy, hydrogen bond, and hydrophobic interactions with proteins while binding energy were found from -6.0 kcal/mol to -7.5 kcal/mol, and it is illustrated that substitute groups in 3 positions plays an important role for biological studies.