Synthesis and anti-inflammatory activities of novel dihydropyranoaurone derivatives

• Published in: Archives of pharmacal research Vol. 40; no. 6; pp. 695 - 703
• Main Authors: Wang, Zheng, Bae, Eun Ju, Han, Young Taek
• Format: Journal Article
• Language: English
• Published: Seoul Pharmaceutical Society of Korea 01.06.2017; 대한약학회
• Subjects: aldehydes; Animals; anti-inflammatory activity; anti-inflammatory agents; Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis; Anti-Inflammatory Agents, Non-Steroidal - chemistry; Anti-Inflammatory Agents, Non-Steroidal - pharmacology; aurones; Benzofurans - chemical synthesis; Benzofurans - chemistry; Benzofurans - pharmacology; Cell Survival - drug effects; derivatization; Dose-Response Relationship, Drug; Enzyme Inhibitors - chemical synthesis; Enzyme Inhibitors - chemistry; Enzyme Inhibitors - pharmacology; Humans; inducible nitric oxide synthase; Lipopolysaccharides - antagonists & inhibitors; Lipopolysaccharides - pharmacology; Macrophages - drug effects; Macrophages - metabolism; Medicine; Mice; Molecular Structure; Nitric Oxide Synthase Type II - antagonists & inhibitors; Nitric Oxide Synthase Type II - metabolism; nitrites; Nitrites - antagonists & inhibitors; Nitrites - metabolism; Pharmacology/Toxicology; Pharmacy; RAW 264.7 Cells; Research Article; Structure-Activity Relationship; structure-activity relationships; 약학; Late-stage derivatization; Aldol reaction; Synthesis; Dihydropyranoaurone; Nitric oxide; Anti-inflammation
• ISSN: 0253-6269; 1976-3786; 1976-3786
• DOI: 10.1007/s12272-017-0910-5

A novel series of dihydropyranoaurone derivatives were synthesized and evaluated as potential anti-inflammatory agents. Late-stage derivatization by versatile piperazine-catalyzed aldol reaction between dihydropyanobenzofuran intermediate 2 and diverse aldehydes readily afforded the novel dihydropyranoaurone analogs. Evaluation of the synthesized dihydropyranoaurone derivatives and related compounds regarding their inhibiting inducible nitric oxide synthase and nitrite production of lipopolysaccaride-stimulated RAW 264.7 cells provided insight into the structure–activity relationship of aurone derivatives. Graphical abstract