6-((2-Oxoindolin-3-ylidene)hydrazineylidene)indolo[2,1-b]quinazolin-12(6H)-one

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A novel unsymmetrical azine, 6-((2-oxoindolin-3-ylidene)hydrazineylidene)indolo[2,1-b]quinazolin-12(6H)-one, was synthesized through a condensation reaction between tryptanthrin-6-hydrazone and isatin in chloroform under reflux conditions. Structural characterization revealed the compound exists as a mixture of geometric isomers with one predominant form. Density functional theory (DFT) calculations identified the E,E configuration as the most stable isomer. The isomerization barriers for both C=N bonds were calculated at approximately 18.5 kcal/mol via nitrogen inversion. Given the established biological activities of tryptanthrin and isatin derivatives, this hybrid azine represents a promising lead compound for developing bifunctional drug candidates.