Synthesis of new O-alkyl and alkyne-azide cycloaddition derivatives of 4'-methoxy licoflavanone: a distinct prenylated flavonoids depicting potent cytotoxic activity

摘要

Prenylated flavonoids represent a unique class of naturally occurring compounds and have proved to be an important source of chemically diverse novel metabolites. Nevertheless, they possess wild array of biological activities. 4'-Methoxy licoflavanone is a prenylated flavonoid isolated from stem bark of Erytherina subrossa. Herein, we report the synthesis of O-alkyl analogs (2a-2m) and 1,2,3 triazole conjugate (3-14) of 4'-methoxy licoflavanone by selective modification at C-7 position in the chromane nucleus. In addition, all the derivatives were evaluated for in vitro antiproliferative activity against a panel of cancer cell lines including pancreatic cancer (Mia PaCa-2), prostate cancer (PC-3), and human leukemia (HL-60) cells. The results revealed that some analogs including 2e and 2m exhibited better cytotoxicity effect than parent compound, specifically on Mia PaCa-2 cell lines.