Synthesis, characterization, computational studies and DPPH scavenging activity of some triazatetracyclic derivatives

Some dihydrobenzo[4,5]imidazo[1,2-c]quinazolines have been synthesized from aldehydes and ketones, using the ketones as both reagents and solvents and tetrahydrofuran (THF) as the solvent for the aldehydes, to yield the triazatetracyclics. The compounds have been characterized with spectroscopy and microanalysis. The crystal structures of 9,9-dimethyl-8,10,17-triazatetracyclo[8.7.0 2,7 .0 11,16 ]heptadeca-1(17),2,4,6,11(16),12,14-heptaene ( I ), 9-butyl-9-methyl-8,10,17-triazatetracyclo[8.7.0.0 2 , 7 .0 11,16 ]heptadeca-(17),2,4,6,11(16),12,14-heptaene ( III ) and 9-phenyl-8,10,17-triazatetracyclo[8.7.0 0 2 7 .0 11,16 ]heptadeca-1(17),2,4,6,11(16),12,14-heptaene ( VIII ) have been discussed. The computed NMR, IR, molecular electrostatic potential and frontier molecular orbitals of compounds I , III and VIII have been discussed. The M06 functional gave most of its values closest to the experimental values for the bond lengths and bond angles of compounds I and III . For compound VIII , none of the functionals gave values for bond lengths and bond angles that were consistent with the experimental values, but M06 gave values closest to experimental values. The 1,1-diphenyl-2-picrylhydrazyl ( DPPH) scavenging activity of the triazatetracyclics showed that compound I exhibits significant DPPH scavenging activity with an IC 50 of 56.18 µM compared to 2.37 µM for ascorbic acid.