Exploring the impact of trifluoromethyl (–CF<sub>3</sub>) functional group on the anti-cancer activity of isoxazole-based molecules: design, synthesis, biological evaluation and molecular docking analysis

Pattanayak, Paramita; Nikhitha, Sripathi; Halder, Debojyoti; Ghosh, Balaram; Chatterjee, Tanmay

doi:10.1039/d4ra02856b

RSC Adv.

2024

DOI: 10.1039/d4ra02856b

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Exploring the impact of trifluoromethyl (–CF₃) functional group on the anti-cancer activity of isoxazole-based molecules: design, synthesis, biological evaluation and molecular docking analysis

Paramita Pattanayak,

Sripathi Nikhitha,

Debojyoti Halder

et al.

Abstract: The effect of –CF3 functional group on the enhancement of anti-breast cancer activity of isoxazole based molecules against MCF-7 is demonstrated.

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Cited by 3 publications

References 31 publications

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Reactivity of (3‐(4‐Fluorophenyl)oxyran‐2‐yl)(naphthalene‐2‐yl)methanone Toward Some Nucleophiles for Preparing Promising Agents with Antimicrobial and Antioxidant Activities

Khalaf,

Kotb,

Abdelwahed

et al. 2024

ChemistrySelect

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Abstract(3‐(4‐Fluorophenyl)oxyran‐2‐yl)(naphthalene‐2‐yl)methanone 2 was prepared from the reaction of 3‐(4‐fluorophenyl)‐1‐(naphthalen‐2‐yl)prop‐2‐en‐1‐one (1) with hydrogen peroxide and reacted with different nucleophiles such as hydrazine hydrate, phenyl hydrazine, thiosemicarbazide to give 4‐hydroxy‐1H‐pyrazole derivatives 3a,b‐4. Also, compound 2 was treated with hydroxylamine hydrochloride to give the substituted 2,3‐dihydroisoxazole 5. Similarly, compound 2 was treated with carbon disulfide, phenyl isothiocyanate, and phenyl isocyanate to give the corresponding compounds 6–8. Various spectroscopic techniques and elemental analysis were used to determine the molecular structures of the new derivatives. All the new analogs were screened against five human pathogenic microbial strains: Escherichia coli and Pseudomonas aeruginosa as Gram‐negative bacteria, Bacillus subtilis and Staphylococcus aureus as Gram‐positive bacteria and the yeast Candida albicans using agar diffusion method. Compound 4 exhibited moderate antimicrobial activity against all the tested microorganisms compared to positive control ciprofloxacin and fluconazole. On the other hand, the free radical scavenging activity of the new compounds using DPPH assay protocol revealed that most of the compounds have a weak reducing activity. Moreover, compounds 4 and 8 were docked against 1KZN protein (DNA gyrase), 3FYV and 5V5Z showing the ability to interact with key amino acid residues and the potential to act as inhibitors.

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Reactivity of (3‐(4‐Fluorophenyl)oxyran‐2‐yl)(naphthalene‐2‐yl)methanone Toward Some Nucleophiles for Preparing Promising Agents with Antimicrobial and Antioxidant Activities

Khalaf,

Kotb,

Abdelwahed

et al. 2024

ChemistrySelect

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show abstract

Isoxazole compounds: Unveiling the synthetic strategy, in-silico SAR & toxicity studies and future perspective as PARP inhibitor in cancer therapy

Malik,

Pal

2024

European Journal of Medicinal Chemistry

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Effects of 1H-1,2,3-Triazole Derivatives of 3-O-Acetyl-11-Keto-Beta-Boswellic Acid from Boswellia sacra Resin on T-Cell Proliferation and Activation

Meyiah,

Avula,

Al-Harrasi

et al. 2024

Pharmaceuticals

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Background: 3-O-acetyl-11-keto-β-boswellic acid (β-AKBA), a triterpene natural product, is one of the main natural products of Boswellia sacra resin (BSR) and has reported biological and immunomodulatory effects. 1H-1,2,3-triazole derivatives of β-AKBA (named 6a–6d) were synthesized from β-AKBA. The 1H-1,2,3-triazole compounds are also known to have a wide range of biological and pharmacological properties as demonstrated by in vitro and in vivo studies. This study aimed to investigate the effects of these 1H-1,2,3-triazole derivatives of β-AKBA on human T-cell proliferation and activation. Methods: PBMCs isolated from healthy donors were activated by anti-CD3/CD28 monoclonal antibodies in the presence of β-AKBA (1) or 1H-1,2,3-triazole derivatives of β-AKBA or DMSO controls. Results: We found that similar to the parent compound β-AKBA (1), derivatives 6a, 6b, and 6d significantly inhibited T-cell expansion/proliferation and reduced the levels of CD25 activation marker on CD4+ and CD8+ T cells without exerting significant cytotoxic effects on T-cell viability at a concentration of 25 µM. However, compound 6c further inhibited T-cell expansion/proliferation and CD25 expression, but had a significant cytotoxic effect on cell viability at similar concentrations of 25 µM. Conclusions: These findings demonstrate the immunoinhibitory effects of β-AKBA (1) and its corresponding triazole derivatives on T-cell proliferation and activation, highlighting the promising therapeutic potential of these compounds in T-cell-mediated diseases.

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Exploring the impact of trifluoromethyl (–CF₃) functional group on the anti-cancer activity of isoxazole-based molecules: design, synthesis, biological evaluation and molecular docking analysis

Abstract: The effect of –CF3 functional group on the enhancement of anti-breast cancer activity of isoxazole based molecules against MCF-7 is demonstrated.

Cited by 3 publications

References 31 publications

Reactivity of (3‐(4‐Fluorophenyl)oxyran‐2‐yl)(naphthalene‐2‐yl)methanone Toward Some Nucleophiles for Preparing Promising Agents with Antimicrobial and Antioxidant Activities

Reactivity of (3‐(4‐Fluorophenyl)oxyran‐2‐yl)(naphthalene‐2‐yl)methanone Toward Some Nucleophiles for Preparing Promising Agents with Antimicrobial and Antioxidant Activities

Isoxazole compounds: Unveiling the synthetic strategy, in-silico SAR & toxicity studies and future perspective as PARP inhibitor in cancer therapy

Effects of 1H-1,2,3-Triazole Derivatives of 3-O-Acetyl-11-Keto-Beta-Boswellic Acid from Boswellia sacra Resin on T-Cell Proliferation and Activation

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Exploring the impact of trifluoromethyl (–CF3) functional group on the anti-cancer activity of isoxazole-based molecules: design, synthesis, biological evaluation and molecular docking analysis

Abstract: The effect of –CF3 functional group on the enhancement of anti-breast cancer activity of isoxazole based molecules against MCF-7 is demonstrated.

Cited by 3 publications

References 31 publications

Reactivity of (3‐(4‐Fluorophenyl)oxyran‐2‐yl)(naphthalene‐2‐yl)methanone Toward Some Nucleophiles for Preparing Promising Agents with Antimicrobial and Antioxidant Activities

Reactivity of (3‐(4‐Fluorophenyl)oxyran‐2‐yl)(naphthalene‐2‐yl)methanone Toward Some Nucleophiles for Preparing Promising Agents with Antimicrobial and Antioxidant Activities

Isoxazole compounds: Unveiling the synthetic strategy, in-silico SAR & toxicity studies and future perspective as PARP inhibitor in cancer therapy

Effects of 1H-1,2,3-Triazole Derivatives of 3-O-Acetyl-11-Keto-Beta-Boswellic Acid from Boswellia sacra Resin on T-Cell Proliferation and Activation

Contact Info

Product

Resources

About

Exploring the impact of trifluoromethyl (–CF₃) functional group on the anti-cancer activity of isoxazole-based molecules: design, synthesis, biological evaluation and molecular docking analysis