Synthesis of Novel Polysubstituted (2SR,4RS)-2-Heteroaryltetrahydro-1,4-epoxy-1-benzazepines and cis-2-Heteroaryl-4-hydroxytetrahydro-1H-1-benzazepines as Antiparasitic Agents.

Abstract New series of polysubstituted (2 SR ,4 RS )-2-heteroaryltetrahydro-1,4-epoxy-1-benzazepines and cis -2-heteroaryl-4-hydroxytetrahydro-1 H -1-benzazepines were designed and synthesized in moderate to high yields using a three-step procedure from ortho -allylanilines. Their antiparasitic activity was evaluated against the extracellular and intracellular forms of Trypanosoma cruzi and Leishmania (Leishmania) infantum parasites. Their cytotoxicity was also determined on Vero and THP-1 mammalian cells. Many of the tested compounds inhibited significantly the growth of extracellular forms of T. cruzi and L. (L.) infantum without showing cytotoxicity on Vero and HTP-1 cells. Only compounds 10h and 14f demonstrated good activity against amastigotes of T. cruzi , but none was able to inhibit the growth of L. (L.) infantum amastigotes.