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Syntheses and Evaluation of the Antioxidant Activity of Novel Methoxypsoralen Derivatives

Syntheses and Evaluation of the Antioxidant Activity of Novel Methoxypsoralen Derivatives

Stavros E Bariamis, Marilena Marin, Constantinos M Athanassopoulos, Christos Kontogiorgis, Zinovia Tsimali, Dionissios Papaioannou, Giovanni Sindona, Giovanni Romeo, Konstantinos Avgoustakis, Dimitra Hadjipavlou-Litina

Eur J Med Chem. 2013 Feb;60:155-69.

PMID: 23291118

Abstract:

A series of 5- and 8-methoxypsoralen (MOP) analogs, suitable for structure-antioxidative/anti-inflammatory activity relationship studies, were synthesized using as key-reactions the selective monobromination of MOPs with N-bromosaccharin and either a Heck reaction or a Suzuki coupling or a Suzuki coupling followed by a Wittig reaction to install side-chains of the acrylate- or benzoate- or cinnamate-type, respectively. The 8-MOP analogs 19 and 24, incorporating at position 5 of the psoralen nucleus a butyl acrylate or a tert-butyl cinnamate moiety, were the most powerful inhibitors of soybean LOX and inhibited effectively lipid peroxidation. Analog 19 was a more potent anti-inflammatory agent than the reference compound indomethacin and of comparable cytocompatibility to 8-MOP whereas analog 24 was a weaker inhibitor of inflammation than indomethacin and significantly more cytotoxic than 8-MOP. The results of the biological tests are discussed in terms of structural characteristics.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP538658	Butyl cinnamate		538-65-8	Price

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