Synthesis and anticancer, antidiabetic activity test of β-hydroxypicolinyl serine ethyl heptanoyl ester (PSEHE)

The novel compounds of β Hydroxypicolinyl serine ethyl heptanoyl ester (PSEHE) were obtained from modification of UK 3A compound that had been known possessing high activity as antifungal, antibacterial and anticancer. From this research it is expected to obtain UK 3A analogues compound that higher yield, more economic and hight activity. The purpose of this study was to synthesize PSEHE compounds which have anticancer and antidiabetic activity. The synthesis of these compounds were carried out in two step reactions. The first step was amidation L-serine ethyl ester hydrochloride with β hydroxypicolinyc acid to produce with β hydroxyl picolinyl serine ethyl ester (PSEE). The second step was esterification of β hydroxyl picolinyl serine ethyl ester with heptanoic acid used DCC and DMAP in chloroform to produce PSEHE. Preliminary analysis was carried out with thin layer chromatography (TLC) and followed by purification using extraction, and the column chromatography on silica gel, eluted with n-hexane and ethyl acetate. Subsequently synthesis product were identified using LCMS Spectrometry, FTIR spectrophotometer, 1H-NMR and 13C-NMR. The pure compound of PSEE from the first step was 85.22% and afterwards pure compound of PSEHE from the second step were 94.48%. The result of toxicity test using Brine Shrimp Lethality Test shown that PSEHE with value LC50 933.25 ppm. The results of cytotoxicity test using Murine Leukemia P-388 cells shown that PSEHE with value IC50 38.0 µg/mL and and the percentage inhibition against to α-glucosidase with value 88.7%.