New quinoxalin‐1,3,4‐oxadiazole derivatives: Synthesis, characterization, in vitro biological evaluations, and molecular modeling studies

Mirzazadeh, Roghieh; Asgari, Mohammad; Barzegari, Ebrahim; Pedrood, Keyvan; Mohammadi‐Khanaposhtani, Maryam; Sherafati, Maedeh; Larijani, Bagher; Rastegar, Hossein; Rahmani, Hojjat; Mahdavi, Mohammad; Taslimi, Parham; Üç, Eda Mehtap; Gülçın, İlhami

doi:10.1002/ardp.202000471

Cited by 15 publications

(8 citation statements)

References 73 publications

(62 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…At 405 nm, absorbances were spectrophotometrically quanti ed. [31] One mole of substrate is hydrolyzed at a rate of one unit of α-glucosidase per minute (pH: 7.4). [32]…”

Section: Biological Assaysmentioning

confidence: 99%

Investigation of cholinesterase and α-glucosidase enzyme activities, and molecular docking and dft studies for 1,2-disubstituted cyclopentane derivatives with phenyl and benzyl units

Artunç,

Çetinkaya,

Taslimi

et al. 2024

Preprint

Self Cite

View full text Add to dashboard Cite

Six known products were prepared from reaction of adipoyl chloride with 1,2,3-trimethoxyphenyl according to the literature. From one of them, four new 1,2-disubstituted cyclopentane derivatives with phenyl and benzyl units were synthesized by reactions such as hydrazonation, catalytic hydrogenation and bromination. The obtained compounds were examined for their in vitro inhibitory activity against acetylcholinesterase (AChE), α-glucosidase, and butyrylcholinesterase (BChE) enzymes. All compounds showed inhibition at nanomolar level with Ki values in the range of 45.53 ± 7.35-631.96 ± 18.88 nM for AChE, 84.30 ± 9.92–622.10 ± 35.14 nM for BChE, and 25.47 ± 4.46–48.87 ± 7.33 for α-Glu. In silico molecular docking studies of the potent compounds were performed in the active sites of AChE (PDB: 1E66), BChE (PDB: 1P0I), and α-glucosidase (PDB: 5ZCC) to compare the effect of bromine atom on the inhibition mechanism. The optimized molecular structures, HOMO-LUMO energies and molecular electrostatic potential maps for the compounds were calculated by using density functional theory with B3LYP/6–31 + G(d,p) and investigated.

show abstract

“…At 405 nm, absorbances were spectrophotometrically quanti ed. [31] One mole of substrate is hydrolyzed at a rate of one unit of α-glucosidase per minute (pH: 7.4). [32]…”

Section: Biological Assaysmentioning

confidence: 99%

Investigation of cholinesterase and α-glucosidase enzyme activities, and molecular docking and dft studies for 1,2-disubstituted cyclopentane derivatives with phenyl and benzyl units

Artunç,

Çetinkaya,

Taslimi

et al. 2024

Preprint

Self Cite

View full text Add to dashboard Cite

show abstract

“…In the continuation of the work of Mirzazadeh et al in discovering new and effective inhibitors against metabolic enzymes, they reported the synthesis of new series of quinoxalin-1,3,4-oxadiazole ( 114 ) derivatives. They demonstrated their inhibitory effects against human carbonic anhydrase (hCA) isoenzymes I and II (carbonic anhydrases I and II), cholinesterase (ACHE and BCHE), and α-glucosidase [ 106 ]. All the targeted compounds displayed better enzymatic inhibitory activities than the standard inhibitors.…”

Section: Six-membered Heterocyclic Compoundsmentioning

confidence: 99%

An Overview of the Biological Evaluation of Selected Nitrogen-Containing Heterocycle Medicinal Chemistry Compounds

Ebenezer

Jordaan

Carena

et al. 2022

IJMS

View full text Add to dashboard Cite

Heterocyclic compounds are a class of compounds of natural origin with favorable properties and hence have major pharmaceutical significance. They have an exceptional adroitness favoring their use as diverse smart biomimetics, in addition to possessing an active pharmacophore in a complex structure. This has made them an indispensable motif in the drug discovery field. Heterocyclic compounds are usually classified according to the ring size, type, and the number of heteroatoms present in the ring. Among different heterocyclic ring systems, nitrogen heterocyclic compounds are more abundant in nature. They also have considerable pharmacological significance. This review highlights recent pioneering studies in the biological assessment of nitrogen-containing compounds, namely: triazoles, tetrazoles, imidazole/benzimidazoles, pyrimidines, and quinolines. It explores publications between April 2020 and February 2022 and will benefit researchers in medicinal chemistry and pharmacology. The present work is organized based on the size of the heterocyclic ring.

show abstract

“…Therefore, it was deduced that 1,3,4-oxadiazole could also serve as an indispensable pharmacophore for new DMI fungicides (Figure 1). In addition, 1,3,4-oxadiazole derivatives are a classic type of fivemembered heterocyclic compounds containing C, N, and O atoms, and have attracted more and more attention due to the importance of oxadiazole derivatives in medicinal chemistry and extensive biological activities, such as antiviral, [16] nematocidal, [17] antifungal, [4,18,19] antitumor, [20][21][22][23] antiinflammatory, [24] α-glucosidase inhibition, [25] and antitubercular activities. [26] Moreover, electron-donating groups (e. g., À O-and-SÀ ) linked with a heteroatomic ring would be conducive to the enhancement of the binding affinity between receptor and ligand, and thus the biological activities of the hybrids could be improved.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antifungal Activity, and Molecular Simulation Study of L–Carvone‐Derived 1,3,4‐Oxadiazole‐Thioether Compounds

Wen

Fan

Lin

et al. 2023

Chemistry & Biodiversity

View full text Add to dashboard Cite

To discover potent antifungal molecules with new and distinctive structures, 20 novel L-carvone-derived 1,3,4-oxadiazolethioether compounds 5 a-5 t were synthesized through multistep reaction of L-carvone, and their structures were confirmed by FT-IR, 1 H-NMR, 13 C-NMR, and HR-MS. The antifungal activities of compounds 5 a-5 t were preliminarily tested by in vitro method, and the results indicated that all of the title compounds displayed certain antifungal activities against the eight tested plant fungi, especially for P. piricola. Among them, compound 5 i (R = p-F) with the most significant antifungal activity deserved further study for discovering and developing novel natural product-based antifungal agents. Moreover, two molecular simulation technologies were employed for the investigation of their structure-activity relationships (SARs). Firstly, a reasonable and effective 3D-QSAR model was established by the comparative molecular field (CoMFA) method, and the relationship of the substituents linked with the benzene rings and the inhibitory activities of the title compounds against P. piricola was elucidated. Then, the binding mode of compound 5 i (R = p-F) and its potential biological target (CYP51) was simulated by molecular docking, and it was found that compound 5 i could readily bind with CYP51 in the active site, and the ligand-receptor interactions involved three hydrogen bonds and several hydrophobic effects.

show abstract

New quinoxalin‐1,3,4‐oxadiazole derivatives: Synthesis, characterization, in vitro biological evaluations, and molecular modeling studies

Cited by 15 publications

References 73 publications

Investigation of cholinesterase and α-glucosidase enzyme activities, and molecular docking and dft studies for 1,2-disubstituted cyclopentane derivatives with phenyl and benzyl units

Investigation of cholinesterase and α-glucosidase enzyme activities, and molecular docking and dft studies for 1,2-disubstituted cyclopentane derivatives with phenyl and benzyl units

An Overview of the Biological Evaluation of Selected Nitrogen-Containing Heterocycle Medicinal Chemistry Compounds

Synthesis, Antifungal Activity, and Molecular Simulation Study of L–Carvone‐Derived 1,3,4‐Oxadiazole‐Thioether Compounds

Contact Info

Product

Resources

About