Synthesis, biological evaluation (antioxidant, antimicrobial, enzyme inhibition, and cytotoxic) and molecular docking study of hydroxy methoxy benzoin/benzil analogous


YAYLI N., BOZDAL G., KAHRİMAN N., KANBOLAT Ş., Bozdeveci A., ALPAY KARAOĞLU Ş. , ...More

BIOORGANIC CHEMISTRY, vol.115, 2021 (Journal Indexed in SCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 115
  • Publication Date: 2021
  • Doi Number: 10.1016/j.bioorg.2021.105183
  • Title of Journal : BIOORGANIC CHEMISTRY
  • Keywords: Hydroxy methoxy benzoin/benzil, Methoxy benzoin/benzil-O-beta-D-glucoside, Antioxidant, Antimicrobial, Enzyme inhibition, Cytotoxic activity, ONE-POT SYNTHESIS, BENZIL DIPHENYLETHANE-1,2-DIONE, CARBONYL-COMPOUNDS, IONIC LIQUIDS, CONDENSATION, OXIDATION, IMIDAZOLIUM, ALDEHYDES, BENZOINS, SALTS

Abstract

In this work, due to the biological activity evaluation, a series of hydroxy methoxy benzoins (1-8), benzils (10-16) and methoxy benzoin/benzil-O-beta-D-glucosides (17-28) were synthesized. Antioxidant (FRAP, CUPRAC, DPPH), antimicrobial (16 microorganisms, and two yeast), enzyme inhibition (alpha-amylase, alpha-glucosidase, AChE, BChE, and tyrosinase) of all synthesized benzoin/benzil analogs were investigated. Benzoins (1-8) showed the most effective antioxidant properties compared to all three methods. Compound 28 against alpha-amylase, compound 9 against alpha-glucosidase, compound 11 against AChE, compound 2 against BChE, and compound 13 against tyrosinase showed the best activities with the better or similar IC50 values as used standards. Hydroxy methoxy benzoin compounds (1-8) among all four groups were seen as the most effective against the tested microorganism. Molecular docking analysis showed that all tested compounds 1-28 (0.01-2.22 mu M) had the best binding affinity against AChE enzyme. Cytotoxic effects of the many of compounds (1-16, 21, and 24) also investigated and it was found that they caused different effects in different cells. The LDH tests of compounds 1a + b, 4, 7, 8, 9, 11, 12, 21, and 24, seemed to be effective compared to the positive control cisplatin. The cytotoxicity of compounds 6 (9.24%) for MCF7 cancer cells, 8 (5.16%) and 4 (8.26%) for HT29 cancer cells, 24 (9.84%) for Hep3B cells and 8 (8.52%), 7 (5.70%), 4 (6.94) and 9 (7.22%) for C6 cells were at normal values. And also cytotoxic activity of four compounds (5, 9, 21, and 24) among the all synthetic groups, were evaluated to the HeLa and RPE. Compound 5 showed anticancer activity on HeLa and RPE cancer cells as much as or better than cisplatin which was used as standard.