Synthesis of pyranochromene and pyranopyrimidine derivatives from substituted natural coumarin isolated from Ammi majus L. and their biological evaluation
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A series of novel coumarin derivatives were synthesized from 6-hydroxy-7-methoxy-4-methyl coumarin which was isolated from the aerial parts of the Egyptian medicinal plant Ammi majus L. (Apiaceae). The key intermediate 3-amino-5-methoxy-1-(4-methoxyphenyl)-10-methyl-8-oxo-1,8-dihydropyrano[3,2-f]chromene-2-carbonitrile (3c) was obtained in one-pot synthesis by treating α-cyanocinnamonitrile (1-c) with the natural compound: 6-hydroxy-7-methoxy-4-methyl coumarin (2). Chemical, elemental and spectroscopic evidences confirmed the structures of the synthesized compounds. Some of the newly synthesized compounds exhibited better anti-inflammatory activities at low concentrations compared with indomethacin as positive control.
KeywordsCoumarin Pyranochromene Pyranopyrimidinochromene Anti-inflammatory
The authors gratefully acknowledge the financial support by Greece and are thankful to the Lab. of organic chemistry (natural product synthesis), Department of Chemistry, Faculty of science Aristotle University of Thessaloniki, Thessaloniki, Greece for the assistance in the performance of some experiments of 1D&2D NMR & MS spectral analyses.
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