We report the synthesis and biological evaluation of three analogues of the natural product (+)-grandifloracin (+)-1. All three analogues exhibit enhanced antiproliferative activity against PANC-1 and HT-29 cells compared to the natural product. The retention of activity in an analogue lacking the enone functional group, 9, implies this structural element is not an essential part of the (+)-grandifloracin pharmacophore.
Ali Khan, M., Wood, P. J., Lamb-Guhren, N. M., Caggiano, L., Kociok-Köhn, G., Tosh, D., & Lewis, S. E. (2014). The enone motif of (+)-grandifloracin is not essential for 'anti-austerity' antiproliferative activity. Bioorganic & Medicinal Chemistry Letters, 24(13), 2815-2819. https://doi.org/10.1016/j.bmcl.2014.04.111