This observationled us to propose that the reaction maybe take place through the initial formation of azomethineylide 4 by decarboxylation of 5',6',7',7a'-tetrahydro-1'H-spiro-[indene-2,3'-pyrro-lo[1,2-c]oxazole]-1,1',3-trione3.Subsequently,1,3-diploar cycloaddition of azomethineylide 4 with acrylates 5 or 1,4-naphthoquinone
6 produces the final products (Scheme 1).
synthesized new series of 2-(4-amino- benzosulfonyl)-5H-benzo[b]carbazole-6,11-dione derivatives by the reaction 1,4-naphthoquinone with 4-aminophenyl sulfone and their subsequent reactions and studied their cytotoxicity evaluation .
Shukla, Synthesis and Biological Evaluation of Novel 1,4-naphthoquinone Derivatives as Antibacterial and Antiviral Agents, Bioorg.
Previous studies on the anticancer activities of this 1,4-naphthoquinone derivative are mostly focused on its cytotoxic properties via the induction of apoptosis and necrosis (Ding et al.
It is worth mentioning that ROS generation and modulation of intracellular signalling pathways have also been associated with the anti-metastatic effects of other 1,4-naphthoquinone derivatives.
Numerous therapeutic drugs, in particular antitumor compounds, are quinone-bearing molecules including anthracyclines (doxorubicin, mitoxanthrone, and daunarubicin), benzoquinones (mitomycin C, geldanamycin), orthonaphthoquinones like [beta]-lapachone, and several synthetic compounds which are currently under clinical trials using 1,4-naphthoquinone
as pharmacophore group [6-9].
Roe et al., "Photooxygenations of 1-naphthols: An environmentally friendly access to 1,4-naphthoquinones
," Tetrahedron, vol.
Fungitoxicity of 1,4-naphthoquinones
to Candida albicans and trichophyton menthagrophytes.
Felipe et al., "DNA damage and inhibition of akt pathway in MCF-7 cells and ehrlich tumor in mice treated with 1,4-naphthoquinones
in combination with ascorbate," Oxidative Medicine and Cellular Longevity, vol.
are derived from naphthalene by the introduction of two carbonyl groups in the 1,4 positions or, less commonly, in the 1,2 positions (1,2-naphthoquinones) .