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. 2021 Jun 30;45(3):788-804.
doi: 10.3906/kim-2012-25. eCollection 2021.

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

Nurettin Yayli  1 , Gözde Kiliç  1 , Gonca Çelik  2 , Nuran Kahriman  2 , Şeyda Kanbolat  3 , Arif Bozdeveci  4 , Şengül Alpay Karaoğlu  4 , Rezzan Aliyazicioğlu  3 , Hasan Erdinç Sellitepe  5 , İnci Selin Doğan  5 , Ali Aydin  6
Affiliations

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

Nurettin Yayli et al. Turk J Chem. .

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

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Conflict of interest statement

CONFLICT OF INTEREST: none declared

Figures

Figure
Figure
Synthesis scheme for the hydroxy benzoin, benzil, and their D-glucoside derivatives (R1 and R2: -H, -OH, or D-Glucose).
See this image and copyright information in PMC

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