Efficient,collective synthesis and nitric oxide inhibitory activity of rubrolides E,F, R,S and their derivatives |
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Authors: | Kongara Damodar Jin-Kyung Kim Jong-Gab Jun |
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Institution: | 1. Department of Chemistry and Institute of Applied Chemistry, Hallym University, Chuncheon 24252, South Korea;2. Department of Biomedical Science, College of Natural Science, Catholic University of Daegu, Gyeungsan-si 38430, South Korea |
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Abstract: | An efficient first synthesis of biologically significant natural butenolides, rubrolides F (1f), R (1r), S (1s) & its 7″,8″-didehydro derivative (1sa), and 3″-bromo rubrolide (1fa) along with the synthesis of rubrolide E (1e) and its di-O-methyl derivative (1ea) is accomplished in a collective fashion from commercially available and inexpensive precursors in overall yields of 14–48.5%. Key features are Wittig-Horner reaction, SeO2-induced tandem allylic hydroxylation/intramolecular cyclization and Knoevenagel condensation. Next, in their inhibitory activity towards nitric oxide (NO) production in lipopolysaccharide-induced RAW 264.7 macrophages as an indicator of anti-inflammatory activity, all compounds displayed good inhibitory activity in a concentration-dependent manner. None of the compound exhibited notable cytotoxicity at the highest concentration (10 μM) and IC50 values are found in the range from 8.53 to 17.85 μM. |
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Keywords: | Rubrolides Wittig-Horner reaction Knoevenagel condensation Nitric oxide Corresponding author |
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