A Novel Sunscreen Agent Having Antimelanoma Activity.

Abstract

A Novel Sunscreen Agent Having Antimelanoma Activity. -A series of dibenzoylmethane derivatives (I) is synthesized and reduced to mono-(II) and dihydroxy compounds (III). The products are evaluated for their sunscreen and cytotoxic activity. Compound (IIIc) appears to be a leading candidate for use as a UV sunscreen agent, also having therapeutical activity against melanoma cells. -(NOGUEIRA, M. A.; MAGALHAES, E. G.; MAGALHAES, A. F.; BILOTI, D. N.; LAVERDE, A. J.; PESSINE, F. B. T.; CARVALHO, J. E.; KOHN, L. K.; ANTONIO, M. A.; MARSAIOLI*, A.

A dibenzoylmethane derivative protects dopaminergic neurons against both oxidative stress and endoplasmic reticulum stress

“…Several beneficial bioactivities of DBM, such as anti-tumor activity (21,27,31), anti-inflammatory activity (18), anti-mutagenesis (7), and iron chelation (44), have previously been reported. Some DBM derivatives have also been used as sunscreens because of their UVA-absorbing activities, but an inability of these derivatives to protect keratinocytes against UVA-induced cytotoxicity has also been reported (1).…”

Anti-African trypanocidal and antimalarial activity of natural flavonoids, dibenzoylmethanes and synthetic analogues

“…The activity of synthetic 1‐(4‐methoxyphenyl)‐2‐benzyl‐3‐(4‐ tert butylphenyl)‐1,3‐propanediol ( 15c , IC50 T 4.6 μ M ) was comparable with that of 1h (IC50 T 4.8 μ M ) 23 . Five of the dibenzoylmethanes had IC50 T values ranging from 8.9 to 11.9 μ M ; however, the most active, 15c and 7‐methoxypongamol ( 11 , IC50 T 8.9 μ M ), were toxic to KB cells (IC50 K 19.1 and 37.1 μ M , respectively).…”

“…Compounds 13a – g were obtained by alkylation of dibenzoylmethane (1,3‐diphenyl‐propane‐dione), Eusolex 8020 and Parsol 1789 using potassium carbonate in acetone. The products were characterized by high‐resolution mass spectrometry (HRMS) and 1 H and 13 C NMR spectroscopy 23 . A second series of derivatives was obtained by reducing the diketones with NaBH 4 at −10°C in methanol producing ketol ( 14 ) and diols ( 15a–c ) 23 .…”

“…The products were characterized by high‐resolution mass spectrometry (HRMS) and 1 H and 13 C NMR spectroscopy 23 . A second series of derivatives was obtained by reducing the diketones with NaBH 4 at −10°C in methanol producing ketol ( 14 ) and diols ( 15a–c ) 23 . Dibenzoyl compound was obtained by Friedel‐Crafts acylation of 1,3‐dimethoxybenzene with phenylacetyl chloride to give 2′,4′‐dimethoxydeoxybenzoin.…”

A dibenzoylmethane derivative protects against hydrogen peroxide-induced cell death and inhibits lipopolysaccharide-induced nitric oxide production in cultured rat astrocytes

“…DBM and its derivatives are small β‐diketone compounds and are minor constituents of licorice (Demizu et al,1992). Several beneficial bioactivities of DBM have been reported; such as antitumor activity (Jackson et al,2002; Nogueira et al,2003; Lin et al,2006), antiinflammatory activity (Hong et al,2004), and antimutagenesis (Choshi et al,1992). Some DBM derivatives have also been used as sunscreens because of their UV A ‐absorbing activities, although an inability of these derivatives to protect keratinocytes against UV A ‐induced cytotoxicity has also been reported (Armeni et al,2004).…”