Synthesis of novel thiosemicarbazone derivatives as antidiabetic agent with enzyme kinetic studies and antioxidant activity
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, cilt.197, sa.12, ss.1284-1294, 2022 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 197 Sayı: 12
- Basım Tarihi: 2022
- Doi Numarası: 10.1080/10426507.2022.2099857
- Dergi Adı: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core
- Sayfa Sayıları: ss.1284-1294
- Anahtar Kelimeler: Thiosemicarbazones, alpha-glucosidase, alpha-amylase, antioxidant, molecular docking, ALPHA-AMYLASE, GLUCOSIDASE INHIBITORS, DISCOVERY, OXIDASE
- Recep Tayyip Erdoğan Üniversitesi Adresli: Evet
Özet
Novel thiosemicarbazone derivatives were synthesized via condensation reactions between the corresponding thiosemicarbazides and 4-(methylsulfonyl)acetophenone. The chemical structures of all compounds were elucidated by infrared (IR), H-1-NMR and C-13-NMR spectroscopy and mass spectrometry. Antioxidant studies of all compounds were performed by using CUPRAC, FRAP, DPPH methods. 2-{1-[4-(Methylsulfonyl)phenyl]ethylidene}-N-phenylhydrazinecarbothioamide (1) possessed good antioxidant activity with an SC50 value of 15.70 mu M which also is higher than standard drug, ascorbic acid. All compounds were evaluated for their antidiabetic properties as alpha-glycosidase and alpha-amylase inhibitors. Compound 1 was found to be the most active compound against alpha-glucosidase and alpha-amylase with IC50 values of 1.58 mu M and 3.24 mu M, respectively. The enzyme kinetic studies demonstrated that compound 1 has a competitive mode of binding. Furthermore, molecular docking studies have elucidated the binding mechanism at the molecular level by examining the molecular interactions between compound 1 and these enzymes.