کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1399268 1501156 2013 15 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Syntheses and evaluation of the antioxidant activity of novel methoxypsoralen derivatives
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Syntheses and evaluation of the antioxidant activity of novel methoxypsoralen derivatives
چکیده انگلیسی

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.

Figure optionsDownload as PowerPoint slideHighlights
► Selective monobromination of methoxypsoralens (MOPs) with N-bromosaccharin.
► Introduction of unsaturated chains in brominated MOPs using Pd-mediated reactions.
► n-Butyl E-3-(8-methoxypsoralen-5-yl)propenoate (19) is the most potent LOX inhibitor.
► Analog 19 was the most potent anti-inflammatory agent, even better than indomethacin.
► Analog 19 presented comparable cytocompatibility to the drug 8-MOP.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: European Journal of Medicinal Chemistry - Volume 60, February 2013, Pages 155–169
نویسندگان
, , , , , , , , , ,