Synthesis and Anticancer Activity of 1‐(Ethyl/Methyl)‐7‐(p‐Methoxybenzyl Amino) and 7‐Amino‐6‐Fluoroquinolone‐Boron Difluoride Complexes

Abstract

Novel 1‐(ethyl/methyl)‐7‐(p‐methoxybenzyl amino) and 7‐amino‐6‐fluoroquinolone‐boron difluoride complexes were synthesized, and their biological activity was studied, comparing the influence of the nature of 7‐substituent as well as N‐1 substituent. The quinolone compounds were characterized by IR, UV‐Vis, 1H, 13C{1H} and 19F{1H} NMR, and mass spectrometry. The antiproliferative effect of the new fluoroquinolone‐boron complexes in breast cancer (BC) derived cell lines MCF‐7 and SKBR‐3 was investigated. Compounds 9 b and 9 a showed antiproliferative in MCF‐7 cells, and 9 b, 11 b, 9 a, 7 a, 7b and 8 a showed similar effects in SKBR‐3 cells. Derivatives with p‐methoxybenzyl amino moieties at C‐7 and an ethyl or methyl group at N‐1 in the fluoroquinolone ring (9 a and 9 b) were the more efficient in both breast cancer cell lines. In addition, an 8‐nitro group to the fluoroquinolone (11 b) improved activity against SKBR‐3 cell proliferation. These compounds represent potential drug candidates for breast cancer treatment.