Synthesis and anticancer activity studies of α-aminoalkylated conjugated nitroalkenes

Abstract

The synthesis of α-aminoalkylated conjugated nitroalkenes with imidazole/LiCi-mediated reaction of conjugated nitroalkenes with N-tosylimines were investigated. The reaction conditions for obtaining the best yield of the aminoalkylted products were optimized in the presence of various tertiary amines and tertiary phosphines in stoichiometric amounts. Activated amines reacted as electrophiles in the Morita-Baylis-Hillman reaction of conjugated nitroalkenes under the influence of imidazole and LiCl affording aminoalylated nitroalkenes. It was found that some of these products exhibited inhibition of human cervical cancer cell proliferation at concentration in the range of 1-10 μM. It was observed that some compounds inhibited microtubule assembly both in vitro and in cells. The results show that such compounds inhibit human cervical cancer cell proliferation probably by perturbing microtubule assembly through tubulin binding.