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practical synthesis of hydroxychromenes and evaluation of their biological activity实际合成hydroxychromenes和评估他们的生物活性.pdf

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practical synthesis of hydroxychromenes and evaluation of their biological activity实际合成hydroxychromenes和评估他们的生物活性

Molecules 2012, 17, 240-247; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Practical Synthesis of Hydroxychromenes and Evaluation of Their Biological Activity Jae-Chul Jung 1 and Seikwan Oh 2,* 1 Institute of Life Science Research, Rexgene Biotech, Ochang, Chungbuk 363-838, Korea 2 Department of Neuroscience and TIDRC, School of Medicine, Ewha Womans University, Seoul 158-710, Korea * Author to whom correspondence should be addressed; E-Mail: skoh@ewha.ac.kr. Received: 5 December 2011; in revised form: 24 December 2011 / Accepted: 26 December 2011 / Published: 28 December 2011 Abstract: A simple and efficient seven steps synthesis of brodifacoum and difethialone from phenylacetyl chloride is described. The key synthetic strategies involve Friedel-Crafts acylation, intramolecular ring cyclization and condensation reaction in the presence of Brønsted-Lowry acids. It was found that brodifacoum showed favorable inhibiting activities on LPS-stimulated nitrite production in BV-2 microglia cells. Brodifacoum exhibited superior anti-inflammatory effects than difethialone. We expect that an efficient linear synthesis of 4-hydroxycoumarin derivatives and key fragments that are useful agents for the modulation of inflammation as well as inhibition of coagulation will be of practical use. Keywords: anti-inflammatory; brodifacoum; coupling reaction; difethialone; Friedel-Crafts acylation; intramolec