[3 + 2] Cycloaddition Synthesis of New (Chromene‐1,3,4‐Oxadiazole) Hybrids Linked to Pyrazole Units as Potential Acetylcholinesterase Inhibitors

ChemistrySelect, Год журнала: 2025, Номер 10(2)

Опубликована: Янв. 1, 2025

Abstract A lot of interest has been gained recently in developing novel acetylcholinesterase (AChE) inhibitors that can alleviate Alzheimer's symptoms. In the current study, we aimed to explore AChE inhibitory activity new chromenes attached 1,3,4‐oxadiazole and/or pyrazole units. The hybrids were obtained via [3 + 2] cycloaddition reaction between appropriate chromene‐based enaminones and hydrazonyl chlorides. inhibition percentages products against recorded at tested concentrations 15 25 µM compared donepezil. 3‐(3‐Acetyl‐1‐(4‐methoxyphenyl)‐1 H ‐pyrazole‐4‐carbonyl)‐6‐(((5‐phenyl‐1,3,4‐oxadiazol‐2‐yl)thio)methyl)‐2 ‐chromen‐2‐one displayed promising with 73.2 87.3, respectively, aforementioned concentrations. Moreover, previous hybrid gave 2,2‐diphenylpicrylhydrazyl (DPPH) using reference ascorbic acid. It had an percentage 86.6 a concentration µM.

Язык: Английский

---

Structure–Activity Relationship of Benzofuran Derivatives with Potential Anticancer Activity

Cancers, Год журнала: 2022, Номер 14(9), С. 2196 - 2196

Опубликована: Апрель 28, 2022

Benzofuran is a heterocyclic compound found naturally in plants and it can also be obtained through synthetic reactions. Multiple physicochemical characteristics versatile features distinguish benzofuran, its chemical structure composed of fused benzene furan rings. derivatives are essential compounds that hold vital biological activities to design novel therapies with enhanced efficacy compared conventional treatments. Therefore, medicinal chemists used core synthesize new applied variety disorders. exhibited potential effectiveness chronic diseases such as hypertension, neurodegenerative oxidative conditions, dyslipidemia. In acute infections, benzofuran revealed anti-infective properties against microorganisms like viruses, bacteria, parasites. recent years, the complex nature number acquired or resistant cancer cases have been largely increasing. anticancer activity lower incidence severity adverse events normally encountered during chemotherapeutic This review discusses structure–activity relationship (SAR) several order elucidate possible substitution alternatives structural requirements for highly potent selective activity.

Язык: Английский

---

Synthesis, molecular docking study and anticancer activity of novel 1,3,4-oxadiazole derivatives as potential tubulin inhibitors

Heliyon, Год журнала: 2023, Номер 9(2), С. e13460 - e13460

Опубликована: Фев. 1, 2023

The current study reports on the synthesis and anticancer efficacy of novel oxadiazole derivatives (8a-f) as tubulin polymerization inhibitors. NMR, mass, elemental studies were used to confirm newly produced compounds. In contrast conventional medicine colchicine, compounds 8e 8f demonstrated stronger sensitivity improved IC50 values in range 3.19–8.21 μM against breast MCF-7, colorectal HCT116, liver HepG2 cancer cell lines. target tested for enzymatic activity enzyme. Compounds shown have most effective inhibitory action among new compounds, with 7.95 9.81 nM, respectively. As compared reference drug, molecular docking investigations developed revealed crucial hydrogen bonding addition hydrophobic interaction at binding site, assisting prediction structural requirements found activity. These findings indicate that 1,3,4-oxadizole scaffold has potential future research into medicines.

Язык: Английский

---

New oxadiazole and pyrazoline derivatives as anti-proliferative agents targeting EGFR-TK: design, synthesis, biological evaluation and molecular docking study

Scientific Reports, Год журнала: 2024, Номер 14(1)

Опубликована: Март 5, 2024

Abstract Two new series of oxadiazole and pyrazoline derivatives were designed synthesized as promising EGFR-TK inhibitors. The in vitro antiproliferative activity was studied against three human cancer cell lines; HCT116, HepG-2 MCF7 using MTT assay. Compound 10c showed the most potent anticancer all lines, with IC 50 range 1.82 to 5.55 μM, while proving safe towards normal cells WI-38 (IC = 41.17 μM) compared reference drug doxorubicin 6.72 μM). active candidates 5a, 9b, 10a, 10b further assessed for their inhibition. best which, compounds 5a 0.09 0.16 μM respectively gefitinib 0.04 Further investigation other EGFR family members, that displayed good activities HER3 HER4 values 0.18 0.37 µM, 0.35 0.58 respectively). Furthermore, evaluated cycle distribution apoptotic induction on cells. It induced mitochondrial pathway increased accumulation ROS. Molecular docking study came agreement biological results. Compounds drug-likeness physicochemical properties.

Язык: Английский

---

An Understanding of Mechanism-Based Approaches for 1,3,4-Oxadiazole Scaffolds as Cytotoxic Agents and Enzyme Inhibitors

Pharmaceuticals, Год журнала: 2023, Номер 16(2), С. 254 - 254

Опубликована: Фев. 7, 2023

The world's health system is plagued by cancer and a worldwide effort underway to find new drugs treat cancer. There has been significant improvement in understanding the pathogenesis of cancer, but it remains one leading causes death. imperative 1,3,4-oxadiazole scaffold possesses wide variety biological activities, particularly for treatment. In development novel 1,3,4-oxadiazole-based drugs, structural modifications are important ensure high cytotoxicity towards malignant cells. These modification strategies have shown promising results when combined with outstanding oxadiazole scaffolds, which selectively interact nucleic acids, enzymes, globular proteins. A mechanisms, such as inhibition growth factors, kinases, contribute their antiproliferative effects. activity different conjugates were tested on cell lines types It demonstrated that hybridization other anticancer pharmacophores mechanisms action targeting various enzymes (thymidylate synthase, HDAC, topoisomerase II, telomerase, thymidine phosphorylase) many proteins proliferation. focus this review highlight potential, molecular docking, SAR studies derivatives inhibiting specific targets, telomerase activity, thymidylate phosphorylase enzyme. purpose summarize recent developments discoveries field using 1,3,4-oxadiazoles.

Язык: Английский

---

Biological Characterization of One Oxadiazole Derivative (5(4‐Hydroxyphenyl)‐2‐(N‐Phenyl Amino)‐1,3,4‐Oxadiazole): In Vitro, In Silico, and Network Pharmacological Approaches

Chemical Biology & Drug Design, Год журнала: 2025, Номер 105(1)

Опубликована: Янв. 1, 2025

ABSTRACT Oxadiazole compounds are of great interest because they have a range biological activities ranging from antioxidants to anticancer agents. Against this background, we wanted demonstrate the antioxidant, enzyme inhibitory, and effects 5(4‐hydroxyphenyl)‐2‐(N‐phenylamino)‐1,3,4‐oxadiazole (Hppo). Antioxidant abilities were measured through free radical scavenging reducing power tests. Enzyme inhibitory studied by cholinesterases, tyrosinase, amylase, glucosidase. The effect was tested on pancreatic cancer cell lines (PANC‐1, CRL‐169) HEK293 lines. compound showed significant antioxidant activity (particularly in CUPRAC (cupric acid‐reducing capacity) assay) properties glucosidase inhibition). In test, strong with apoptotic signaling pathways. These results confirmed molecular modeling bioinformatics tools. Thus, our findings can provide novel versatile for development multidirectional drugs pharmaceutical industry.

Язык: Английский

---

Exploration of 1,3,4‐oxadiazoles Engrafted With Indole and Phthalimide Scaffolds as Multi Target Peroxidase, Acetylcholinesterase, and Butyrylchloinesterase Inhibitors: Synthesis, DFT Calculations, and Molecular Docking Studies

ChemistrySelect, Год журнала: 2025, Номер 10(6)

Опубликована: Фев. 1, 2025

Abstract Here, we present the structural and pharmacological characteristics of 2‐(4‐(5‐(3,5‐disubstituted‐1 H ‐indol‐2‐yl)‐1,3,4‐oxadiazol‐2‐yl)phenyl)isoindoline‐1,3‐diones 5(a‐h) as a strong antioxidant anti‐Alzheimer's disease activity using synergistic combination theoretical experimental techniques. The structures novel compounds were analyzed by spectral analysis (IR, NMR Mass spectrometry). DFT calculations for selected applying B3LYP hybrid functional 6–31G (d, p) basis set. predictions regarding ADMET properties, drug‐likeness, toxicity, including favorable bioavailability all synthesized disclosed. All newly 5(a–h) illustrated well to comparable inhibitory potentials ranging from IC 50 values 12.12 ± 0.02 µM 36.31 0.26 µM, 04.08 0.86 12.42 0.32 08.05 0.06 26.36 0.52 against peroxidase , acetylcholinesterase (AChE) butyrylcholinesterase (BChE) respectively. Amongst, compound 5a showed excellent with 0.86, peroxidase, Finally, aforesaid taken in silico molecular modeling cytochrome c (PDB id: 2 × 08), ID: 7E3H), 4BDS).

Язык: Английский

---

New 1,3,4-Oxadiazole and 1,2,3-Triazole Derivatives as Anti-Proliferative Agents: Design, Synthesis, Biological Evaluation, in Silico Docking and Dft Studies

Опубликована: Янв. 1, 2025

Язык: Английский

---

Secosteroid – 1,3,4-Oxadiazole Hybrids: Synthesis and Evaluation of Their Activity Against Hormone-Dependent Breast Cancer Cells

The Journal of Steroid Biochemistry and Molecular Biology, Год журнала: 2025, Номер unknown, С. 106745 - 106745

Опубликована: Март 1, 2025

Язык: Английский

---

Synthesis, in Silico Analysis, Anticancer Activity and Photophysical Properties of Novel Benzisoxazoles

Опубликована: Янв. 1, 2025

Язык: Английский

---