Synthesis of hydroxy benzoin/benzil analogs and investigation of their antioxidant, antimicrobial, enzyme inhibition, and cytotoxic activities


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Yaylı N. , Bozdal G. , Celik G. , Kahriman N. , Kanbolat Ş. , Bozdeveci A., ...More

TURKISH JOURNAL OF CHEMISTRY, vol.45, no.3, pp.788-804, 2021 (Journal Indexed in SCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 45 Issue: 3
  • Publication Date: 2021
  • Doi Number: 10.3906/kim-2012-25
  • Title of Journal : TURKISH JOURNAL OF CHEMISTRY
  • Page Numbers: pp.788-804
  • Keywords: Hydroxy benzoin/benzil, benzoin/benzi1-O-beta-D-glucoside, antioxidant, antimicrobial, enzyme inhibition, cytotoxic activity, ONE-POT SYNTHESIS, CARBONYL-COMPOUNDS, BENZYL-ALCOHOLS, IONIC LIQUIDS, SOLVENT-FREE, OXIDATION, CONDENSATION, BENZILS, IMIDAZOLIUM, DERIVATIVES

Abstract

In this study, hydroxy benzoin (1-7), benzil (8-14), and benzoin/benzil-O-beta-D-glucosides (15-25) were synthesized to investigate their biological activities. An efficient method for synthesizing hydroxy benzoin compounds (1-7) was prepared from four different benzaldehydes using an ultrasonic bath. Then, antioxidant (FRAP, CUPRAC, and DPPH), antimicrobial (3 Gram (-), 4/6 Gram (+), one tuberculosis and one fungus), and enzyme inhibition (acetylcholinesterase, butyrylcholine esterase, tyrosinase, alpha-amylase, and alpha- glucosidase) for the all synthesized compounds (1-25) were evaluated. And also, four most active compounds (4, 12, 18a+b, and 25) from each group were evaluated to the human cervical cancer cell line (HeLa) and anticancer screening tests against the human retinal normal cell line (RPE). Compound 4 showed HeLa and RPE cancer cell activities as much as cisplatin. The synthesized compounds were characterized by spectroscopic methods (NMR, FT-IR, UV, LC-QTOF-MS) and the ACD NMR program's help.