Design, synthesis, and enzyme inhibition evaluation of some novel Mono- and Di-O-β-D-Glycopyranosyl Chalcone analogues with molecular docking studies

Barut, Burak; Sahin, Huseyin; Tatar Yılmaz, Gizem; ÇELİK, Gonca; YAYLI, Nurettin

doi:10.55730/1300-0527.3527

Design, synthesis, and enzyme inhibition evaluation of some novel Mono- and Di-O-β-D-Glycopyranosyl Chalcone analogues with molecular docking studies

Gonca ÇELİK, (Karadeniz Teknik Üniversitesi, Fen Fakültesi, Kimya Bölümü, Trabzon, Türkiye)

Gizem TATAR, (Karadeniz Teknik Üniversitesi, Tıp Fakültesi, Biyoistatistik ve Tıbbi Bilişim Anabilim Dalı, Trabzon, Türkiye)

HÜSEYİN ŞAHİN, (Giresun Üniversitesi, Espiye Meslek Yüksekokulu, Giresun, Türkiye)

Burak BARUT, (Karadeniz Teknik Üniversitesi, Eczacılık Fakültesi, Biyokimya Anabilim Dalı, Trabzon, Türkiye)

Nurettin YAYLI (Karadeniz Teknik Üniversitesi, Eczacılık Fakültesi, Farmakognozi Anabilim Dalı, Trabzon, Türkiye)

Turkish Journal of Chemistry

11 0

Yıl: 2023 Cilt: 47 Sayı: 1 Sayfa Aralığı: 171 - 184 Metin Dili: İngilizce DOI: 10.55730/1300-0527.3527 İndeks Tarihi: 13-03-2023

Design, synthesis, and enzyme inhibition evaluation of some novel Mono- and Di-O-β-D-Glycopyranosyl Chalcone analogues with molecular docking studies

Öz:

In this study, some novel mono- and di-O-β-D-glycopyranosyl chalcone analogs were designed, synthesized, and characterized. The chalcone derivatives were synthesized with good yields by base-catalyzed Claisen-Schmidt condensation in EtOH solution. Then these chalcones were reacted with TAGBr (2,3,4,6-tetra-O-acetyl-α-D-glucopyranosylbromide) in dry acetone under the anhydrous condition at 0–5 °C. Deacylated was carried out by the Zemplen’s method with $NaOCH_3$ in dry methanol results in substituted chalcone- O-glycosides (mono- and di-O-β-D-glycopyranosyl chalcone analogs). The chemical structures of all synthesized compounds were elucidated based on IR, NMR spectral data, and mass spectrometry. Further, the compounds (7a-c, 8a-c, 12a-c, 16a-c, and 17a-c) were tested for their enzyme inhibition activity against α-glycosidase, tyrosinase, and AChE with in vitro and in silico analysis. Amongst them, compounds 12a-c, 16a-c, and 17a-c displayed moderate or less enzyme inhibition activity against α-glycosidase while other compounds 7a-c and 8a-c) were not active. Remarkably interesting enzyme inhibition effects, with $IC_{50}$ values below 30.59 ± 0.30 μM were recorded with 7c $(IC_{50}=11.07 ± 0.55 μM)$ against tyrosinase.

Anahtar Kelime: Chalcone enzyme inhibition glycoside glycosylation molecular docking

Belge Türü: Makale Makale Türü: Araştırma Makalesi Erişim Türü: Erişime Açık

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APA	ÇELİK G, Tatar Yılmaz G, Sahin H, Barut B, YAYLI N (2023). Design, synthesis, and enzyme inhibition evaluation of some novel Mono- and Di-O-β-D-Glycopyranosyl Chalcone analogues with molecular docking studies. , 171 - 184. 10.55730/1300-0527.3527
Chicago	ÇELİK Gonca,Tatar Yılmaz Gizem,Sahin Huseyin,Barut Burak,YAYLI Nurettin Design, synthesis, and enzyme inhibition evaluation of some novel Mono- and Di-O-β-D-Glycopyranosyl Chalcone analogues with molecular docking studies. (2023): 171 - 184. 10.55730/1300-0527.3527
MLA	ÇELİK Gonca,Tatar Yılmaz Gizem,Sahin Huseyin,Barut Burak,YAYLI Nurettin Design, synthesis, and enzyme inhibition evaluation of some novel Mono- and Di-O-β-D-Glycopyranosyl Chalcone analogues with molecular docking studies. , 2023, ss.171 - 184. 10.55730/1300-0527.3527
AMA	ÇELİK G,Tatar Yılmaz G,Sahin H,Barut B,YAYLI N Design, synthesis, and enzyme inhibition evaluation of some novel Mono- and Di-O-β-D-Glycopyranosyl Chalcone analogues with molecular docking studies. . 2023; 171 - 184. 10.55730/1300-0527.3527
Vancouver	ÇELİK G,Tatar Yılmaz G,Sahin H,Barut B,YAYLI N Design, synthesis, and enzyme inhibition evaluation of some novel Mono- and Di-O-β-D-Glycopyranosyl Chalcone analogues with molecular docking studies. . 2023; 171 - 184. 10.55730/1300-0527.3527
IEEE	ÇELİK G,Tatar Yılmaz G,Sahin H,Barut B,YAYLI N "Design, synthesis, and enzyme inhibition evaluation of some novel Mono- and Di-O-β-D-Glycopyranosyl Chalcone analogues with molecular docking studies." , ss.171 - 184, 2023. 10.55730/1300-0527.3527
ISNAD	ÇELİK, Gonca vd. "Design, synthesis, and enzyme inhibition evaluation of some novel Mono- and Di-O-β-D-Glycopyranosyl Chalcone analogues with molecular docking studies". (2023), 171-184. https://doi.org/10.55730/1300-0527.3527

APA	ÇELİK G, Tatar Yılmaz G, Sahin H, Barut B, YAYLI N (2023). Design, synthesis, and enzyme inhibition evaluation of some novel Mono- and Di-O-β-D-Glycopyranosyl Chalcone analogues with molecular docking studies. Turkish Journal of Chemistry, 47(1), 171 - 184. 10.55730/1300-0527.3527
Chicago	ÇELİK Gonca,Tatar Yılmaz Gizem,Sahin Huseyin,Barut Burak,YAYLI Nurettin Design, synthesis, and enzyme inhibition evaluation of some novel Mono- and Di-O-β-D-Glycopyranosyl Chalcone analogues with molecular docking studies. Turkish Journal of Chemistry 47, no.1 (2023): 171 - 184. 10.55730/1300-0527.3527
MLA	ÇELİK Gonca,Tatar Yılmaz Gizem,Sahin Huseyin,Barut Burak,YAYLI Nurettin Design, synthesis, and enzyme inhibition evaluation of some novel Mono- and Di-O-β-D-Glycopyranosyl Chalcone analogues with molecular docking studies. Turkish Journal of Chemistry, vol.47, no.1, 2023, ss.171 - 184. 10.55730/1300-0527.3527
AMA	ÇELİK G,Tatar Yılmaz G,Sahin H,Barut B,YAYLI N Design, synthesis, and enzyme inhibition evaluation of some novel Mono- and Di-O-β-D-Glycopyranosyl Chalcone analogues with molecular docking studies. Turkish Journal of Chemistry. 2023; 47(1): 171 - 184. 10.55730/1300-0527.3527
Vancouver	ÇELİK G,Tatar Yılmaz G,Sahin H,Barut B,YAYLI N Design, synthesis, and enzyme inhibition evaluation of some novel Mono- and Di-O-β-D-Glycopyranosyl Chalcone analogues with molecular docking studies. Turkish Journal of Chemistry. 2023; 47(1): 171 - 184. 10.55730/1300-0527.3527
IEEE	ÇELİK G,Tatar Yılmaz G,Sahin H,Barut B,YAYLI N "Design, synthesis, and enzyme inhibition evaluation of some novel Mono- and Di-O-β-D-Glycopyranosyl Chalcone analogues with molecular docking studies." Turkish Journal of Chemistry, 47, ss.171 - 184, 2023. 10.55730/1300-0527.3527
ISNAD	ÇELİK, Gonca vd. "Design, synthesis, and enzyme inhibition evaluation of some novel Mono- and Di-O-β-D-Glycopyranosyl Chalcone analogues with molecular docking studies". Turkish Journal of Chemistry 47/1 (2023), 171-184. https://doi.org/10.55730/1300-0527.3527