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羟基苯偶姻/苯偶酰类似物的合成及其抗氧化、抗菌、酶抑制和细胞毒性活性的研究。

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

作者信息

Yayli Nurettin, Kiliç Gözde, Çelik Gonca, Kahriman Nuran, Kanbolat Şeyda, Bozdeveci Arif, Alpay Karaoğlu Şengül, Aliyazicioğlu Rezzan, Sellitepe Hasan Erdinç, Doğan İnci Selin, Aydin Ali

机构信息

Department of Pharmacognosy, Faculty of Pharmacy, Karadeniz Technical University, Trabzon Turkey.

Department of Chemistry, Faculty of Science, Karadeniz Technical University, Trabzon Turkey.

出版信息

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

Abstract

In this study, hydroxy benzoin ( ), benzil ( ), and benzoin/benzil-O-β-D-glucosides ( ) were synthesized to investigate their biological activities. An efficient method for synthesizing hydroxy benzoin compounds ( - ) 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 ( ) were evaluated. And also, four most active compounds ( , , , and ) 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 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.

摘要

在本研究中,合成了羟基苯偶姻( )、苯偶酰( )和苯偶姻/苯偶酰 -O-β-D-葡萄糖苷( )以研究它们的生物活性。使用超声浴从四种不同的苯甲醛制备了一种合成羟基苯偶姻化合物( - )的有效方法。然后,对所有合成化合物( )进行了抗氧化(FRAP、CUPRAC和DPPH)、抗菌(3种革兰氏阴性菌、4/6种革兰氏阳性菌、1种结核杆菌和1种真菌)以及酶抑制(乙酰胆碱酯酶、丁酰胆碱酯酶、酪氨酸酶、α-淀粉酶和α-葡萄糖苷酶)评估。此外,对每组中四种活性最高的化合物( 、 、 和 )进行了人宫颈癌细胞系(HeLa)评估以及针对人视网膜正常细胞系(RPE)的抗癌筛选试验。化合物 对HeLa和RPE癌细胞的活性与顺铂相当。通过光谱方法(NMR、FT-IR、UV、LC-QTOF-MS)并借助ACD NMR程序对合成的化合物进行了表征。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c192/10454678/7732613df75a/turkjchem-45-788-fig001.jpg

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