AI Article Synopsis
- A new compound called benzo[]indolonaphthyridinium was created unexpectedly through a reaction involving β-carbolinium derivatives and 1,2-cyclohexadione, following Westphal reaction conditions.
- This new compound shows strong fluorescence in polar solvents and has a high affinity for binding to DNA through intercalation.
- Additionally, similar DNA-binding sempervirine derivatives were synthesized from specific 1,2-diketones, indicating that the structure of the starting materials influences the reaction pathway.
Article Abstract
A novel type of azoniahetarene, namely, benzo[]indolonaphthyridinium, was unexpectedly formed by the reaction of -alkylated β-carbolinium derivatives and the enolizable 1,2-cyclohexadione under typical conditions of a Westphal reaction. The products exhibit high fluorescence intensities in polar solvents (Φ = 0.52-0.67) and bind to DNA by intercalation with high affinity ( = 1.5 × 10 M). Furthermore, under the same conditions, DNA-binding sempervirine derivatives were synthesized in a Westphal reaction from 1,2-diketones that have at least one non-enolizable α-carbon atom, which shows that the reaction pathway is determined by the substrate structure.
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| http://dx.doi.org/10.1021/acs.joc.1c02755 | DOI Listing |
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