THE SYNTHESIS OF FIRST REPRESENTATIVES OF GLYCOSYL AMINO PHOSPHONATES BASED ON THE D-GLUCOSAMINE
Α-Aminophosphonic acids are bioisosteres of natural amino acids, and they can act as antagonists of amino acids in active centers of enzymes or other cellular receptors. Some α-aminophosphonates may demonstrate antibiotic, antiviral, anticancer activities usually in combination with low toxicity. In this work, two α-aminophosphonates were synthesized for the first time in which the phosphonate moiety was attached to the amino group of 2-deoxy-2-amino-D-glucopyranose. The three-component Kabachnik-Fields reaction and its two-component variation, the Pudovik reaction, were used to synthesize these compounds. A comprehensive study was carried out for antimicrobial activity. It was discovered that both compounds do not inhibit the growth of the test microorganisms. For the synthesized compounds, the anticancer activity was also measured against a number of tumor cell lines: cervical epithelioid carcinoma (M-HeLa), breast adenocarcinoma (MCF-7), human duodenal adenocarcinoma (HuTu 80), and prostate adenocarcinoma (PC3) cell lines. These compounds demonstrated cytotoxicity against studied cancer cell lines at concentration of 100 μМ and low toxicity to healthy human embryo lung cells (WI38). The largest decrease in the viability of MCF-7 cell line was demonstrated by one of the compounds, which was 88% at the concentration of 100 μM.