Synthesis and Anticancer Activity of Amide Derivatives of 1,2-Isoxazole Combined 1,2,4-Thiadiazole

Shahinshavali, Shaik; Sreenivasulu, Reddymasu; Guttikonda, Venkata R.; Kolli, Deepti; Rao, Mandava V. Basaveswara

doi:10.1134/s1070363219020257

Cited by 57 publications

(6 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…General procedures for the synthesis of catalyst and compounds 3 a-3 k, spectral data of 3 a-3 k and 1 H NMR, 13 C NMR and mass spectra of 3 a-3 k are available in supporting information.…”

Section: Supporting Information Summarymentioning

confidence: 99%

“…[2] Derivatives of isoxazole exhibit a diverse range of biological and pharmacological activities such as antithrombotic, [3] antibacterial, [4] antagonist, [5] antiviral, [6,7] antitumor, [8] anti-HIV, [9] herbicidal, [10] insecticidal [11] and fungicidal. [12] Isoxazole core has been present in drugs such as sulfamethoxazole [13] contains antibiotic properties, muscimol [14] used as a selective GABAA agonist, ibotenic acid [15] that acts as a neurotoxin, parecoxib [16] shows COX-2 inhibitory properties, and leflunomide [17] behaves as an immunosuppressant agent (Figure 1). The desirable pharmacological activities of isoxazole core is may be due to the two adjacent electronegative heteroatoms participating in hydrogen bond donor-acceptor interactions with enzymes and receptors.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Regioselective Synthesis of 3, 5‐Disubstituted Isoxazole Catalyzed by Cu₂O−ZnO Nanocomposite

Pardeshi¹,

Labhane²,

Disale³

et al. 2022

ChemistrySelect

View full text Add to dashboard Cite

Cu 2 OÀ ZnO nanocatalyst has been successfully employed for the [3 + 2] cycloaddition reaction of propargyl ester with in situ generated nitrile oxide from aromatic hydroximyl chlorides under base-free and mild temperature conditions for the regioselective synthesis of 3, 5-disubstituted isoxazoles at a low loading of catalyst. The catalyst can be reused in further catalytic reactions up to five cycles without significant loss in its catalytic activity. The catalyst was characterized by using powder XRD, TEM, SEM and EDS. This developed methodology has advantages such as simplicity, excellent yields, shorter reaction time, and excellent functional group compatibility.

show abstract

“…General procedures for the synthesis of catalyst and compounds 3 a-3 k, spectral data of 3 a-3 k and 1 H NMR, 13 C NMR and mass spectra of 3 a-3 k are available in supporting information.…”

Section: Supporting Information Summarymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Regioselective Synthesis of 3, 5‐Disubstituted Isoxazole Catalyzed by Cu₂O−ZnO Nanocomposite

Pardeshi¹,

Labhane²,

Disale³

et al. 2022

ChemistrySelect

View full text Add to dashboard Cite

show abstract

“…Microbial diseases are becoming global threat because of the effective decrease in the potential activity of anti-microbial therapies and also bacteria's like Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumonia, Acinetobacter baumannii, Pseudomonas aeruginosa, Enterobacter theses families of organism becomes serious threat to the society because of change in the pathology of these organisms [3,4].…”

Section: Introductionmentioning

confidence: 99%

Design, Binding Affinity Studies and in Silico Admet Predictions of Novel Isoxazoles as Potential Anti-Bacterial

SAI

JAYS

Madriwala

2022

Int J Curr Pharm Sci

View full text Add to dashboard Cite

Objective: The objective of the study is to design novel isoxazole derivatives, predicting their interactions with the selected target proteins and determining the ADMET properties of potent molecules using recent computational methods. Methods: With the intent to discover potent novel antibacterial, we have designed a set of compounds containing the isoxazole nucleus by using software tools like Discovery studios, PyRx, PyMOL, SWISSPDB. ADMET studies were carried out by using SWISS ADMET and pkCSM. Molecular docking studies were carried out on the target proteins of both gram-positive and gram negative bacteria in order to assesses binding affinity for the proteins. Results: Designed scaffold was designed by Benzene Derivatives Tethered with 5(4-chloro-3-nitro phenyl-1-yl) isoxazole. All the derivatives were docked against the three proteins, namely DNA Ligase (PDB ID: 3PN1), Topoisomerase (PDB ID: 3TTZ), Sterol demethylase (PDB ID: 5FSA), The compound JJC3F has shown best binding score against DNA ligase, sterol demethylase protein. Further, compound JJC3A has shown a better binding affinity towards topoisomerase than the standard drugs. Conclusion: Molecular Docking study indicates that isoxazole derivatives may be effective inhibitors for the different microbial proteins. Additionally, in silico ADMET studies predicts drug-like features. Hence, these compounds may be considered as leads and further investigation of their analogues may help in development of novel drugs for the treatment of microbial diseases.

show abstract

“…Different types of heterocyclic derivatives such as isoxazole are used extensively as agrochemicals in medicine; indeed, they are efficient in anticancer chemotherapy [15,18]. Researchers have found that the isoxazole ring imparts it with anticancer [19,20], hypoglycemic [21], pain killing, bactericidal [20,22], antiviral (for HIV) [23], and antiinflammatory [24] activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Novel Isoxazole-Amide Analogues as Anticancer and Antioxidant Agents

Eid

Hawash

Amer

et al. 2021

BioMed Research International

View full text Add to dashboard Cite

Cancer now is one of the leading causes of mortality in the world. There has been a lot of effort to discover new anticarcinogenic agents that allow treatment with fewer side effects. A series of isoxazole-carboxamide derivatives (2a–2g) were synthesised and evaluated for their cytotoxic activity against breast (MCF-7), cervical (HeLa), and liver (Hep3B) cancer cell lines and their antioxidant activity in the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. The results showed that 2d and 2e were the most active compounds against Hep3B cells, with a half-maximal inhibitory concentration (IC50) of around 23 μg/ml; 2d showed the highest activity against HeLa cells, with an IC50 15.48 μg/ml. However, 2a had the lowest IC50 (39.80 μg/ml) against MCF-7 cells. By contrast, compound 2g was inactive against all cancer cell lines, with IC50 values >400 μg/ml. Both 2d and 2e reduced Hep3B secretion of alpha-fetoprotein (to 1829.33 ± 65.91 ng / ml and 1758.66 ± 54.04 ng / ml , respectively). Furthermore, in cell cycle analysis, 2d and 2e induced a delay in the G2/M phase of 18.07%, which is similar to the doxorubicin positive control. Moreover, 2d and 2e reduced the necrosis rate of Hep3B threefold and instead shifted the cells to apoptosis. Our results indicate that 2d and 2e have potent and promising anticancer activity. However, compound 2a was the most active as antioxidant agent ( I C 50 = 7.8 ± 1.21 μ g / ml ) compared with Trolox as a positive control (IC50 2.75 μg/ml).

show abstract

Synthesis and Anticancer Activity of Amide Derivatives of 1,2-Isoxazole Combined 1,2,4-Thiadiazole

Cited by 57 publications

References 19 publications

Regioselective Synthesis of 3, 5‐Disubstituted Isoxazole Catalyzed by Cu₂O−ZnO Nanocomposite

Regioselective Synthesis of 3, 5‐Disubstituted Isoxazole Catalyzed by Cu₂O−ZnO Nanocomposite

Design, Binding Affinity Studies and in Silico Admet Predictions of Novel Isoxazoles as Potential Anti-Bacterial

Synthesis and Biological Evaluation of Novel Isoxazole-Amide Analogues as Anticancer and Antioxidant Agents

Contact Info

Product

Resources

About

Synthesis and Anticancer Activity of Amide Derivatives of 1,2-Isoxazole Combined 1,2,4-Thiadiazole

Cited by 57 publications

References 19 publications

Regioselective Synthesis of 3, 5‐Disubstituted Isoxazole Catalyzed by Cu2O−ZnO Nanocomposite

Regioselective Synthesis of 3, 5‐Disubstituted Isoxazole Catalyzed by Cu2O−ZnO Nanocomposite

Design, Binding Affinity Studies and in Silico Admet Predictions of Novel Isoxazoles as Potential Anti-Bacterial

Synthesis and Biological Evaluation of Novel Isoxazole-Amide Analogues as Anticancer and Antioxidant Agents

Contact Info

Product

Resources

About

Regioselective Synthesis of 3, 5‐Disubstituted Isoxazole Catalyzed by Cu₂O−ZnO Nanocomposite

Regioselective Synthesis of 3, 5‐Disubstituted Isoxazole Catalyzed by Cu₂O−ZnO Nanocomposite