Synthesis, characterization and computational studies of 1,3-bis[(E)-furan 2-yl)methylene]urea and 1,3-bis[(E)-furan-2-yl) methylene]thiourea

Abstract

Urea and thiourea derivatives: 1,3-bis[(E)-furan-2-yl)methylene]urea (BFMU) and 1,3-bis[(E)-furan-2-yl)methylene]thiourea (BFMT) were synthesized and characterized by spectrometry analyses (UV, IR, 1H NMR and 13C NMR). They were screened for antibacterial (Salmonella typhi, Staphylococcus aureus, Pseudomonas aeruginosa, Xanthomonas axonopodis and Streptococcus bovis) and antifungal (Fusa rium oxysporum, Colletotrichum gloeosporioides and Cercospora zeae-maydis) activ ities. Quantum chemical calculations of frontier molecular orbital energies (EHOMO and ELUMO),andtheirassociatedglobalparameterswerecarriedoutbyDFTlevelsoftheory, with complete relaxation in the potential energy surface using 6-31G* basis set (DFT/ B3LYP/6-31G*). Azomethine functional groups (C=N) appeared at δ 7.6 ppm and δ 7.0 ppm in the proton spectra, the peaks between δ 105 and δ 160 ppm of 13C spectra represent the methylene carbons(C=C). BFMUisabetterinhibitor of P.aeruginosa and S. bovis, while BFMTisabetterinhibitorofS.typhi,S.aureusandX.axonopodisandthe fungi isolates (F. oxysporum, C. gloeosporioides and C. zeae-maydis) used. The global parameters agreed favorably with the experimental results, indicating the higher activity of BFMT