New chiral Mannich adducts of di-tert-butylphenols and a bicyclic imine – Synthesis and antiproliferative activity

Abstract Tests of antiproliferative activity of Mannich adducts of aromatic nucleophiles and a chiral bicyclic imine revealed a di- tert -butylphenol derivative as a promising compound for further exploration. To study the influence of substitution pattern and a configuration of stereogenic centers on the inhibition of cancer cell growth, a series of Mannich bases were obtained with a good to high diastereoselectivity from the reaction of the imine and three isomeric di- tert- butylphenols. Six new enantiopure adducts were isolated and fully characterized. Selected derivatives were shown to exhibit an interesting antiproliferative activity comparable to cisplatin.