Synthesis and cytotoxicity of Baylis-Hillman template derived betulinic acid-triazole conjugates

Several alkynes and azides were prepared starting from betulinic acid and Baylis-Hillman reaction derived allylic alcohols. These alkynes and azides were then coupled under click cycloaddition conditions to obtain functionalized betulinic acid-triazole conjugates. Similarly, pyrazinyl- and indolylbetulinic acid-triazoles were also prepared employing cycloaddition chemistry. All the synthetic compounds were tested for their cytotoxicity against murine breast cancer (4T1) and human pancreatic cancer (MIA PaCa-2) cell lines. Based on these in vitro assays, two series of compounds have been identified as lead compounds for further development. (C) 2016 Elsevier Ltd. All rights reserved.