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

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, H-1 NMR and C-13 NMR). They were screened for antibacterial (Salmonella typhi, Staphylococcus aureus, Pseudomonas aeruginosa, Xanthomonas axonopodis and Streptococcus bovis) and antifungal (Fusarium oxysporum, Colletotrichum gloeosporioides and Cercospora zeae-maydis) activities. Quantum chemical calculations of frontier molecular orbital energies (E-HOMO and E-LUMO), and their associated global parameters were carried out by DFT levels of theory, with complete relaxation in the potential energy surface using 6-31G* basis set (DFT/B3LYP/6-31G*). Azomethine functional groups (C=N) appeared at delta 7.6 ppm and delta 7.0 ppm in the proton spectra, the peaks between delta 105 and delta 160 ppm of C-13 spectra represent the methylene carbons (C=C). BFMU is a better inhibitor of P. aeruginosa and S. bovis, while BFMT is a better inhibitor of S. typhi, S. aureus and X. axonopodis and the 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.