- Cytotoxicity effects of di- and tri-hydroxybenzaldehydes as a chemopreventive potential agent on tumor cells
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As part of our earlier search for new compounds with improved biological activities including antioxidant, anti-inflammatory, and tumor growth inhibition activities, we synthesized 2,4,5-trihydroxybenzaldehyde (2,4,5-THBA) from commercially available Sesa
- Tseng, Tsui-Hwa,Tsheng, Yen-Min,Lee, Yean-Jang
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- Synthetic method for rugchalcone A, B and their derivatives and their anti-inflammatory use
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The present invention provides an effective anti-inflammatory agent which does not have a side effect. The present inventors have invented an effective method for synthesizing 2-aroylbenzofuran, rugchalcone A, B, and a derivative thereof at high yield by a Rap-Stoermer reaction between substituted salicylaldehyde and phenacyl bromide. Moreover, the inventors have evaluated an anti-inflammatory effect of the compound in lipopolysaccharide-induced RAW 264.7 macrophages. The compound remarkably inhibits the generation of nitrogen oxide which mediates inflammation without having cytotoxicity at a concentration of 10 andmu;M, and an IC_50 value is in the range of 0.57-13.27 andmu;M. From 2-aroylbenzofuran synthesized according to the preset invention, compound 4 (99.6%; IC_50 = 0.57), rugchalcone B (compound 2)(99.3%; IC_50 = 4.13), compound 7 (96.8%; IC_50 = 1.90), and compound 8 (74.3%; IC_50 = 0.99) show a maximum inhibiting activity. Such a result shows that compounds 2, 4, 7, and 8 having 4-hydroxyphenyl group and/or a hydroxyl group in a 5- and/or 6- position of a benzofuran motif can be functioned as a structure needed in developing an iNOS inhibitor with respect to the application thereof to the anti-inflammatory field.COPYRIGHT KIPO 2017
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Paragraph 0030-0031
(2017/08/09)
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- Synthesis and biological evaluation of 2-aroylbenzofurans, rugchalcones A, B and their derivatives as potent anti-inflammatory agents
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An efficient synthesis of 2-aroylbenzofurans, rugchalcones A, B and their derivatives was accomplished in excellent yields by the Rap–Stoermer reaction between substituted salicylaldehydes and phenacyl bromides. Later their anti-inflammatory effects were evaluated in lipopolysaccharide (LPS)-induced RAW-264.7 macrophages. The compounds were exhibited exceptional potency against inflammatory mediated NO production with no cytotoxicity at 10?μM concentration and IC50values are found in the range from 0.75 to 13.27?μM. Among the 2-aroylbenzofurans prepared in this study, compounds 4 (99.6%; IC50?=?0.57), rugchalcone B (2) (99.3%; IC50?=?4.13), 7 (96.8%; IC50?=?1.90) and 8 (74.3%; IC50?=?0.99) were showed the maximum inhibitory activity. This study suggests that compounds 2, 4, 7 and 8 which are having 4-hydroxyphenyl group and/or hydroxy (–OH) group at 5- and/or 6-position of benzofuran motif could be considered as a promising scaffolds for the further development of iNOS inhibitors for potential anti-inflammatory applications.
- Seo, Young Hwa,Damodar, Kongara,Kim, Jin-Kyung,Jun, Jong-Gab
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supporting information
p. 1521 - 1524
(2016/07/29)
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