Novel Benzoic Acid Derivatives Bearing Quinazolin‐4(3H)‐one Ring: Synthesis, Characterization, and Inhibition Effects on α‐Glucosidase and α‐Amylase
Yazarlar (1)
Doç. Dr. Feyzi Sinan TOKALI
Kafkas Üniversitesi, Türkiye
| Makale Türü | Özgün Makale (SSCI, AHCI, SCI, SCI-Exp dergilerinde yayınlanan tam makale) | ||
| Dergi Adı | CHEMISTRYSELECT (Q3) | ||
| Dergi ISSN | 2365-6549 Wos Dergi Scopus Dergi | ||
| Dergi Tarandığı Indeksler | SCI-Expanded | ||
| Makale Dili | İngilizce | Basım Tarihi | 12-2022 |
| Cilt / Sayı / Sayfa | 7 / 48 / – | DOI | 10.1002/slct.202204019 |
| Makale Linki | http://dx.doi.org/10.1002/slct.202204019 | ||
| Özet |
| Abstract In this study, new benzoic acid derivatives of the quinazolinone ring, which is one of the biologically active members of nitrogen‐containing heterocyclic compounds, were synthesized with excellent yields (98–90 %). The structures of the novel compounds ( 1 – 12 ) were characterized with Fourier‐transform Infrared (FTIR), Nuclear Magnetic Resonance ( 1 H NMR– 13 C NMR), and High‐Resolution Mass Spectroscopy (HRMS). α‐Glucosidase and α‐Amylase inhibition properties were examined to evaluate the anti‐diabetic properties of the synthesized compounds. For α‐Glucosidase, molecules showed IC 50 in ranging of >100–3.468±0.270 μM and K i s in ranging of >100–3.310±0.326 μM. For α‐Amylase, molecules showed IC 50 in ranging of >100–1.215±0.225 μM. 4‐[(2‐[(4‐phenylpiperazin‐1‐yl)methyl]‐4‐oxoquinazolin‐3(4 H )‐ylimino)methyl]benzoicacid ( 10 ) has the strongest inhibitory effect for both enzymes. It is 5.4 times more potent inhibitor for α‐Glucosidase and 34.9 times more potent for α‐Amylase than the standard inhibitor Acarbose. Also, the molecular docking study was carried out for the most active compound for the determination of ligand‐enzyme interactions. Binding affinities of the most active compound were calculated as −5.978 kcal/mol and −5.548 kcal/mol for α‐Glucosidase and α‐Amylase, respectively. The aromatic ring and the aminomethyl group of the quinazoline and the carboxyl group moieties have played a critical role in the inhibition. |
| Anahtar Kelimeler |
| alpha-Amylase | Diabetes | alpha-Glucosidase | Inhibition | Quinazolin-4(3H)-one |
BM Sürdürülebilir Kalkınma Amaçları
| Atıf Sayıları | |
| WoS | 36 |