Synthesis and Cytotoxic Activity of Novel ۹-[Hydroxy(Substitutedphenyl) Methyl]-۲,۲-Dimethyl-۲,۳,۸,۹-Tetrahydro-۴H,۱۰H-Pyrano [۲,۳-f ]Chromene-۴,۱۰-Diones

Chromanone derivatives demonstrate remarkable cytotoxity against a varieties of cancer cell lines. Novel ۹-[hydroxy(substitutedphenyl)methyl]-۲,۲-dimethyl-۲,۳,۸,۹- tetrahydro-۴H,۱۰H-pyrano[۲,۳-f]chromene-۴,۱۰-diones as Glyasperin analogues were synthesized in four steps from known ۴-chromone ۱. The key step was the preparation of chromane dione ۵a by regioselective intramolecular cyclization reaction in ۸۵% yield. Condensation of ۵a with substituted aromatic aldehydes afforded corresponding alpha hydroxybenzyl analogues ۶a-۶e. The cytotoxic study of the synthesized compounds against breast cancer human cell line (T۴۷D) showed moderate cytotoxic activities (IC۵۰=۱۶-۴۰ μM) compared to the positive control drug vincristin (IC۵۰=۲.۵ μM).

کلیدواژه ها:

Chromane ، Aldol reaction ، Cytotoxicity ، Chromanone ، Glyasperin analogues