Current Advancement in the Oxadiazole-Based Scaffolds as Anticancer Agents

Kapoor, Garima; Bhutani, Rubina; Pathak, Dharam Pal; Chauhan, Garima; Kant, Ravi; Grover, Parul; Nagarajan, K.; Siddiqui, Shadab Ahmad

doi:10.1080/10406638.2021.1886123

Cited by 14 publications

(2 citation statements)

References 103 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The therapeutic profile of furan-based molecules has attracted medicinal researchers to design and develop anticancer agents which could play a pivotal role in cancer therapy [ 1 , 15 , 16 ]. In addition to this, oxadiazole and triazole ring systems, which are part of many natural products, have become the focus of pharmacologists and medicinal chemists on account of their medicinal and pharmacology activities, especially in the field of oncology [ 17 , 18 ].…”

Section: Introductionmentioning

confidence: 99%

Exploring the Synergistic Anticancer Potential of Benzofuran–Oxadiazoles and Triazoles: Improved Ultrasound- and Microwave-Assisted Synthesis, Molecular Docking, Hemolytic, Thrombolytic and Anticancer Evaluation of Furan-Based Molecules

et al. 2022

View full text Add to dashboard Cite

Ultrasound- and microwave-assisted green synthetic strategies were applied to furnish benzofuran–oxadiazole 5a–g and benzofuran–triazole 7a–h derivatives in good to excellent yields (60–96%), in comparison with conventional methods (36–80% yield). These synthesized derivatives were screened for hemolysis, thrombolysis and anticancer therapeutic potential against an A549 lung cancer cell line using an MTT assay. Derivatives 7b (0.1%) and 5e (0.5%) showed the least toxicity against RBCs. Hybrid 7f showed excellent thrombolysis activity (61.4%) when compared against reference ABTS. The highest anticancer activity was displayed by the 5d structural hybridwith cell viability 27.49 ± 1.90 and IC50 6.3 ± 0.7 μM values, which were considerably lower than the reference drug crizotinib (IC50 8.54 ± 0.84 μM). Conformational analysis revealed the spatial arrangement of compound 5d, which demonstrated its significant potency in comparison with crizotinib; therefore, scaffold 5d would be a promising anticancer agent on the basis of cytotoxicity studies, as well as in silico modeling studies.

show abstract

Section: Introductionmentioning

confidence: 99%

Exploring the Synergistic Anticancer Potential of Benzofuran–Oxadiazoles and Triazoles: Improved Ultrasound- and Microwave-Assisted Synthesis, Molecular Docking, Hemolytic, Thrombolytic and Anticancer Evaluation of Furan-Based Molecules

et al. 2022

View full text Add to dashboard Cite

show abstract

“…[ 3,4 ] Various therapeutic agents such as furamizole, a nitrofuran derivative with excellent antibacterial activity, HIV‐integrase inhibitor raltegravir, and antihypertensive agents like tiodazosin and nesapidil are based on the 1,3,4‐oxadiazole moiety. The 1,3,4‐oxadiazole ring exhibits manifold biological activities such as anti‐inflammatory, [ 5,6 ] antimicrobial, [ 7–10 ] anticonvulsant, [ 11–13 ] analgesic, [ 14,15 ] anticancer, [ 16 ] antitubercular, [ 17 ] and hypolipidemic activities. [ 18 ] Effective pharmacological potency of 1,3,4‐oxadiazoles may be attributed to the presence of the toxophoric –N═C–O– linkage, which could react with the nucleophilic centers of the microbial cell.…”

Section: Introductionmentioning

confidence: 99%

In silico molecular docking studies of oxadiazole and pyrimidine bearing heterocyclic compounds as potential antimicrobial agents

Desai

Vaghani

Jethawa

et al. 2021

Archiv der Pharmazie

View full text Add to dashboard Cite

Microbial resistance is a major problem faced by the scientific community. It has created an urgent need to develop antimicrobial agents with novel structures and mechanisms of action. With this aim, a series of novel 1,3,4‐oxadiazoles bearing 3,4‐dihydropyrimidine heterocyclic motifs 4a–l were designed and synthesized. One‐pot Biginelli synthesis is pivotal due to the use of readily available chemicals, shorter reaction time, and ecofriendly synthesis with a good yield. The structures of the synthesized molecules were characterized and confirmed by infrared, 1H nuclear magnetic resonance (NMR), 13C NMR, and mass spectroscopic techniques. The title compounds were screened against Gram‐positive and ‐negative strains of bacteria and fungi using the Mueller–Hinton broth method. Compound 4d was found to be the most promising against Escherichia coli (12.5 µg/ml), whereas the same compound showed good activity against Staphylococcus aureus at a concentration of 50 µg/ml. Other compounds of the same series, 4c and 4h, displayed moderate activity against Streptococcus pyogenes at a concentration of 50 µg/ml. Furthermore, results of the antifungal activity tests revealed that compound 4i showed promising activity against all the strains of fungi, Candida albicans, Aspergillus niger, and Aspergillus clavatus, at concentrations of 100, 50, and 100 µg/ml, respectively. Molecular docking also showed that these compounds had a significant binding affinity (Glide docking score: −7.74 to −6.531) for DNA gyrase, engaging in a series of bonded and nonbonded interactions with residues lining the active site. The results of molecular docking study validated the experimental findings, thereby providing an initiation mark to optimize this motif using a structure‐based drug design approach.

show abstract

Synthesis and Evaluation of 3,5‐Disubstituted‐1,2,4‐Oxadiazolyl Benzamides as Potential Anti‐Breast Cancer Agents: In Vitro and In Silico Studies

Asad,

Karim,

Sanobar

et al. 2024

Chemistry & Biodiversity

View full text Add to dashboard Cite

Herein, the synthesis, anti‐cancer evaluation, and in silico studies of a series of 1,2,4‐oxadiazole compounds (8‐15) are disclosed. The synthesized molecules were tested in vitro for anti‐cancer activity against MCF‐7, MDA‐MB‐231, HeLa, Ishikawa cell lines and human embryonic kidney (HEK‐293) cell lines. Among the synthesized compounds, 9 and 15 exhibited significant cytotoxicity, with IC50 values of 7.82 μM and 6.02 μM, respectively, against MCF‐7 cell line, better than that of anti‐breast cancer drug, tamoxifen (IC50 = 11.92 μM), used as control. Significantly, both 9 and 15 exhibited very low toxicity (IC50 > 20 µM) against normal HEK‐293 cells. This suggests them as potentially effective anti‐cancer lead molecules. The in vitro anti‐cancer data was supported by in silico studies which also identified compounds 9 and 15 as potent inhibitors of the 17β‐hydroxysteroid dehydrogenase1 (17β‐HSD1) proteins, demonstrating strong interactions and stability The atom‐based QSAR model exhibited high accuracy, significant regression, and predictive reliability, aiding in understanding and optimizing biological activity. The drug‐likeness study of compounds 9 and 15 indicated favorable pharmacokinetics, with in silico toxicity predictions showing compound 15 to be non‐toxic. These findings suggest compounds 9 and 15 as potential lead molecules against breast cancer.

show abstract

Current Advancement in the Oxadiazole-Based Scaffolds as Anticancer Agents

Cited by 14 publications

References 103 publications

Exploring the Synergistic Anticancer Potential of Benzofuran–Oxadiazoles and Triazoles: Improved Ultrasound- and Microwave-Assisted Synthesis, Molecular Docking, Hemolytic, Thrombolytic and Anticancer Evaluation of Furan-Based Molecules

Exploring the Synergistic Anticancer Potential of Benzofuran–Oxadiazoles and Triazoles: Improved Ultrasound- and Microwave-Assisted Synthesis, Molecular Docking, Hemolytic, Thrombolytic and Anticancer Evaluation of Furan-Based Molecules

In silico molecular docking studies of oxadiazole and pyrimidine bearing heterocyclic compounds as potential antimicrobial agents

Synthesis and Evaluation of 3,5‐Disubstituted‐1,2,4‐Oxadiazolyl Benzamides as Potential Anti‐Breast Cancer Agents: In Vitro and In Silico Studies

Contact Info

Product

Resources

About