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

Authors: NURETTİN YAYLI, GÖZDE KILIÇ, GONCA ÇELİK, NURAN KAHRİMAN, ŞEYDA KANBOLAT, ARİF BOZDEVECİ, ŞENGÜL ALPAY KARAOĞLU, REZZAN ALİYAZICIOĞLU, HASAN ERDİNÇ SELLİTEPE, İNCİ SELİN DOĞAN, ALİ AYDIN

Abstract: In this study, hydroxy benzoin (1-7), benzil (8-14), and benzoin/benzil-O-β-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, α-amylase, and α- 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.

Keywords: Hydroxy benzoin/benzil, benzoin/benzil-O-β-D-glucoside, antioxidant, antimicrobial, enzyme inhibition, cytotoxic activity

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