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Dergiler / Turkish Journal of Chemistry / 2021 / Cilt: 45 - Sayı: 3

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

Rezzan ALİYAZICIOĞLU
Şeyda KANBOLAT
Hasan Erdinç SELLİTEPE
Nuran KAHRİMAN
Şengül ALPAY KARAOĞLU
Arif BOZDEVECİ
İnci Selin DOĞAN
Gonca ÇELİK
Ali AYDIN
Nurettin YAYLI
Gözde KILIÇ
Sayfa
788–804
Yayın Tarihi
2022-11-04
DOI
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⚡ TL;DR(1 Cümlede Hızlı Çıkarım)

The synthesized compounds were characterized by spectroscopic methods (NMR, FT-IR, UV, LC-QTOF-MS) and the ACD NMR program’s help.

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Amaç & Hipotez: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.
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Temel Bulgular & Veri:An efficient method for synthesizing hydroxy benzoin compounds (1-7) was prepared from four different benzaldehydes using an ultrasonic bath.
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Sonuç & Katkı:The synthesized compounds were characterized by spectroscopic methods (NMR, FT-IR, UV, LC-QTOF-MS) and the ACD NMR program’s help.
🔬Tür:Araştırma Makalesi
📍Kapsam:Genişletilmiş Akademik Örneklem
⚙️Değişkenler:Alan Parametreleri

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.

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Bu Makaleye Atıf Yap

ALİYAZICIOĞLU, R., KANBOLAT, Ş., SELLİTEPE, H. E., KAHRİMAN, N., KARAOĞLU, Ş. A., BOZDEVECİ, A., DOĞAN, İ. S., ÇELİK, G., AYDIN, A., YAYLI, N., KILIÇ, G. (2022). Synthesis of hydroxy benzoin/benzil analogs and investigation of their antioxidant, antimicrobial, enzyme inhibition, and cytotoxic activities. Turkish Journal of Chemistry, Cilt: 45 - Sayı: 3, 788–804. https://ajindex.com/articles/601814

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Kaynakça (13)

  1. Vermerris W, Nicholson R. Phenolic Compound Biochemistry. New York, NY, USA: Springer, 2006
  2. Chen Y T, Barletta G L, Haghjoo K, Cheng J T, Jordan F. Reactions of benzaldehyde with thiazolium salts in Me2 SO: evidence for initial formation of 2-(a-hydroxybenzyl)thiazolium by nucleophilic addition and for dramatic solvent effects on benzoin formation. Journal of Organic Chemistry 1994; 59: 7714-7722
  3. Sawada H, Okazaki M, Morita D, Kuroda T, Matsuno K, et al. Riccardin C derivatives as anti-MRSA agents: structure-activity relationship of a series of hydroxylated bis (bibenzyl)s. Bioorganic & Medicinal Chemistry Letters 2012; 22 (24): 7444-7447
  4. Bilir G, Demir A S, Ozcubukcu S. Enzyme-catalyzed trans-benzoin condensation. Journal of the Turkish Chemical Society, Section A: Chemistry 2018; 5 (2): 737-750
  5. Sathyanarayana A, Prabusankar G. (±)Methanodibenzodiazocine tethered [C-H]δ+ functional site: study towards benzoin condensation and Baylis-Hillman reactions. Journal of Chemical Sciences 2015; 127 (5): 821-831
  6. Suh Y, Lee J, Kim S, Rieke R D. Direct preparation of benzylic manganese reagents from benzyl halides, sulfonates, and phosphates and their reactions: applications in organic synthesis. Journal of Organometallic Chemistry 2003; 684: 20-36
  7. Skonieczny K, Jazwinski J, Gryko D T. The Synthesis of Imidazo [1,2-] phenanthridines, Phenanthro-[9,10-d]imidazoles, and Phenanthro[9’,10’:4,5]imidazo[1,2-f]-phenanthridines via Intramolecular Oxidative Aromatic Coupling. Synthesis 2017; 49 (20): 4651- 4662
  8. Sun T, Zhang Y, Qiu B, Wang Y, Qin Y et al. Rhodium-(I)-catalyzed carboacylation aromatization cascade initiated by regioselective C-C activation of benzocyclobutenones. Angewandte Chemie International Edition 2018; 57 (11): 2859-2863
  9. Schwaerzer K, Bellan A, Zoeschg M, Karaghiosoff, K, Knochel, P. Magnesium aldimines prepared by addition of organomagnesium halides to 2,4,6-trichlorophenyl isocyanide: synthesis of 1,2-dicarbonyl derivatives. Chemistry A European Journal 2019; 25 (40): 9415- 9418
  10. Lapworth A. CXXII. Reactions involving the addition of hydrogen cyanide to carbon compounds. Part II. Cyanohydrins regarded as complex acids. Journal of the Chemical Society, Transactions 1904; 85: 1206-1214
  11. Roger A, Marvel C S. Benzoin. Organic Syntheses 1921; 1: 33
  12. Clarke H T, Dreger E E. Benzil. Organic Syntheses 1941; 1: 87
  13. Skobridis K, Theodorou V, Weber E. A very simple and chemoselective air oxidation of benzoins to b