Synthesis and antiproliferative activities of quebecol and its analogs

Pericherla, K.; Shirazi, A.N.; Rao, V.K.; Tiwari, R.; DaSilva, N.; Mccaffrey, K.T.; Beni, Y.A.; González-Sarrías, A.; Seeram, N.P.; Parang, K.; Kumar, A. Synthesis and antiproliferative activities of quebecol and its analogs. Bioorganic Medicinal Chemistry Letters, 2013, 23, 5329-5331.


Simple and efficient synthesis of quebecol and a number of its analogs was accomplished in five steps. The synthesized compounds were evaluated for antiproliferative activities against human cervix adenocarcinoma (HeLa), human ovarian carcinoma (SK-OV-3), human colon carcinoma (HT-29), and human breast adenocarcinoma (MCF-7) cancer cell lines. Among all the compounds, 7c, 7d, 7f, and 8f exhibited antiproliferative activities against four tested cell lines with inhibition over 80% at 75 μM after 72 h, whereas, compound 7b and 7g were more selective towards MCF-7 cell line. The IC50 values for compounds 7c, 7d, and 7f were 85.1 μM, 78.7 μM, and 80.6 μM against MCF-7 cell line, respectively, showing slightly higher antiproliferative activtiy than the synthesized and isolated quebecol with an IC50 value of 104.2 μM against MCF-7.