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Synthesis and biological activity of derivatives of the marine quinone avarone

European Journal of Medicinal Chemistry, 2010
Nine alkyl(aryl)thio derivatives of the marine sesquiterpene quinone avarone were synthesized by nucleophilic addition of thiols or thiophenol to avarone. In most cases only one regioisomer was obtained. Their cytotoxic activities, brine shrimp lethality and antibacterial activity were evaluated, as well as those of some previously synthesized avarone ...
Tatjana Božić   +2 more
exaly   +5 more sources

Avarol and avarone, two new anti-inflammatory agents of marine origin

European Journal of Pharmacology, 1994
The anti-inflammatory activity of avarol and avarone, sesquiterpenoid derivatives from the Mediterranean sponge Dysidea avara, was investigated. Both compounds potently inhibited paw oedema induced by carrageenan (approximated ED50 = 9.2 and 4.6 mg/kg, p.o., respectively) as well as ear oedema induced by 12-O-tetradecanoylphorbol acetate (TPA; ED50 ...
Maria Luisa Ferrándiz   +2 more
exaly   +3 more sources

Effect of avarol and avarone on in vitro-induced microsomal lipid peroxidation

Toxicology, 1992
Lipid peroxidation was employed as an experimental model to study the antioxidant properties of avarol, a sesquiterpenoid hydroquinone and of its quinone, avarone. In the NADPH- or ascorbate-linked lipid peroxidation, avarol and avarone were shown to be more effective as inhibitors than in the t-BuOOH-dependent peroxidative process.
Guglielmo Rosario Domenico Villani
exaly   +6 more sources

Enantioselective Total Synthesis of Avarol and Avarone

Angewandte Chemie - International Edition, 1999
Formation of the C11-C1' bond through application of Barton's radical decarboxylation and quinone addition is the cornerstone of a new convergent and concise synthesis of the marine metabolites avarol (1) and avarone (2; see scheme), for which antimitotic, antileukemic, and antiviral effects have been reported.
Emmanuel A Theodorakis
exaly   +3 more sources

Synthesis and biological activity of amino acid derivatives of avarone and its model compound [PDF]

open access: yesBioorganic and Medicinal Chemistry, 2015
A series of eighteen derivatives of marine sesquiterpene quinone avarone and its model system tert-butylquinone with amino acids has been synthesized by nucleophilic addition of amino acids to the quinones. In vitro cytotoxic activity toward human cancer cell lines (HeLa, A549, Fem-X, K562, MDA-MB-453) and normal MRC-5 cell line was determined. Several
Jovana Vilipić   +2 more
exaly   +6 more sources

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