Synthesis of ferrocenyl pyrazole-containing chiral aminoethanol derivatives and their inhibition against A549 and H322 lung cancer cells

Abstract

A series of novel ethyl 3-ferrocenyl-1-(2-hydroxy-3-(phenylamino)propyl)-1H-pyrazole-5-carboxylate derivatives with optical activity (4) was synthesized by microwave-assisted reaction of substituted aniline and ethyl 3-ferrocenyl-1-(oxiran-2-ylmethyl)-1H-pyrazole-5-carboxylate that was prepared from ethyl 3-ferrocenyl-1H-pyrazole-5-carboxylate and (R)- or (S)-oxiran-2-ylmethyl 4-methylbenzenesulfonate. Structures of the compounds were characterized by means of IR, 1H NMR and mass spectroscopy. Preliminary biological evaluation showed that all of the compounds could suppress the growth of A549 and H322 lung cancer cells. Among all of the tested compounds 4a, 4b and 4d were more effective and might perform their action through cell cycle arrest. Moreover, although the inhibition differences between R and S enantiomers are mostly not so significant, (R)-4b displayed more effective inhibition than (S)-4b.