Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece.
Eur J Med Chem. 2009 Dec;44(12):5012-7. doi: 10.1016/j.ejmech.2009.09.004. Epub 2009 Sep 9.
Angular [7,8]-fused coumarins were obtained from the reaction of [2,3]-fused phenols with DMAD and PPh(3), while linear [6,7]-fused coumarins were formed from the analogous reaction of [3,4]-fused phenols with DMAD and PPh(3). These compounds were tested in vitro for antioxidant activity and they found to present significant scavenging activity. In parallel, these new compounds were evaluated in vivo for anti-inflammatory activity and they found to inhibit the carrageenin-induced paw edema (34-65%). Although their interaction with the free stable radical DPPH was low, the methyl 2,2-dimethyl-8-oxo-3,8-dihydro-2H-furo[2,3-h]chromene-6-carboxylate was the most potent (65%) in the in vivo experiment. The later seems to be a potent soybean Lipoxygenase inhibitor and does not acquire gastrointestinal toxicity.
角型[7,8]-稠合香豆素可由[2,3]-稠合苯酚与 DMAD 和 PPh(3)反应得到，而线型[6,7]-稠合香豆素则可由类似的[3,4]-稠合苯酚与 DMAD 和 PPh(3)反应得到。这些化合物在体外进行了抗氧化活性测试，发现它们具有显著的清除活性。同时，这些新化合物在体内进行了抗炎活性评价，发现它们能抑制角叉菜胶诱导的足肿胀（34-65%）。虽然它们与游离稳定自由基 DPPH 的相互作用较弱，但 2,2-二甲基-8-氧代-3,8-二氢-2H-呋喃并[2,3-h]色烯-6-羧酸甲酯在体内实验中具有最强的抑制活性（65%）。后者似乎是一种有效的大豆脂氧合酶抑制剂，且不会产生胃肠道毒性。
