Organocatalysis in the Synthesis of 1,2,3‐Triazoyl‐zidovudine Derivatives: Synthesis and Preliminary Antioxidant Activity

Gomes, Carolina B.; Balaguez, Renata A.; Larroza, Allya; Smaniotto, Thiago Ângelo; Domingues, Micaela; Casaril, Angela Maria; Silva, Márcio S.; Rodrigues, Oscar E. D.; Savegnago, Lucielli; Alves, Diego

doi:10.1002/slct.202003355

Cited by 8 publications

(3 citation statements)

References 67 publications

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“…Furthermore, they are used to clarify the underlying pathophysiology, such as the oxidative stress commonly associated with these conditions ( Balmus et al, 2016 ; Zhang et al, 2017 ). In this sense, the use of animal tissue in investigating the antioxidant properties of new compounds is well accepted in the literature ( Chagas et al, 2015 ; Gomes et al, 2020 ; Vogt et al, 2018 ).…”

Section: Methodsmentioning

confidence: 99%

Exploring the antioxidant potential of chalcogen-indolizines throughout in vitro assays

Garcia,

da Rocha,

Presa

et al. 2024

PeerJ

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Reactive oxygen species (ROS) and reactive nitrogen species (RNS) are highly reactive molecules produced naturally by the body and by external factors. When these species are generated in excessive amounts, they can lead to oxidative stress, which in turn can cause cellular and tissue damage. This damage is known to contribute to the aging process and is associated with age-related conditions, including cardiovascular and neurodegenerative diseases. In recent years, there has been an increased interest in the development of compounds with antioxidant potential to assist in the treatment of disorders related to oxidative stress. In this way, compounds containing sulfur (S) and/or selenium (Se) have been considered promising due to the relevant role of these elements in the biosynthesis of antioxidant enzymes and essential proteins with physiological functions. In this context, studies involving heterocyclic nuclei have significantly increased, notably highlighting the indolizine nucleus, given that compounds containing this nucleus have been demonstrating considerable pharmacological properties. Thus, the objective of this research was to evaluate the in vitro antioxidant activity of eight S- and Se-derivatives containing indolizine nucleus and different substituents. The in vitro assays 1,1-diphenyl-2-picryl-hydrazil (DPPH) scavenger activity, ferric ion (Fe3+) reducing antioxidant power (FRAP), thiobarbituric acid reactive species (TBARS), and protein carbonylation (PC) were used to access the antioxidant profile of the compounds. Our findings demonstrated that all the compounds showed FRAP activity and reduced the levels of TBARS and PC in mouse brains homogenates. Some compounds were also capable of acting as DPPH scavengers. In conclusion, the present study demonstrated that eight novel organochalcogen compounds exhibit antioxidant activity.

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Section: Methodsmentioning

confidence: 99%

Exploring the antioxidant potential of chalcogen-indolizines throughout in vitro assays

Garcia,

da Rocha,

Presa

et al. 2024

PeerJ

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“…[26] Zidovudine is an FDA-approved AIDS prevention and treatment drug that is also on the list of the World Health Organization's Essential Medicines. [27] Ciprofloxacin, the second generation of fluoroquinolone exhibits excellent antimicrobial activity, pharmacokinetic properties, and few side effects, and has been used in clinical practice for the treatment of various bacterial infections for nearly three decades. [28] The WHO has recommended Ciprofloxacin as a second-line agent for the treatment of tuberculosis (TB), primarily in cases of resistance or intolerance to first-line anti-TB therapy.…”

Section: Introductionmentioning

confidence: 99%

“…The antibacterial, antitumor and antimalarial properties of ferrocene derivatives have attracted a lot of attention [26] . Zidovudine is an FDA‐approved AIDS prevention and treatment drug that is also on the list of the World Health Organization's Essential Medicines [27] . Ciprofloxacin, the second generation of fluoroquinolone exhibits excellent antimicrobial activity, pharmacokinetic properties, and few side effects, and has been used in clinical practice for the treatment of various bacterial infections for nearly three decades [28] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Ester‐Linked Ursolic Acid‐Based Hybrid Compounds: Potential Antibacterial and Anticancer Agents

Khwaza

Oyedeji

Oselusi

et al. 2023

Chemistry & Biodiversity

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The molecular hybridization of two or more drugs into a single molecule is an effective drug design approach to reduce pill burden and improve patient treatment adherence. Ursolic acid-based hybrid compounds were synthesized and characterized followed by molecular docking studies. In vitro studies against various bacterial strains and human cancer cells (MDA-MB-231, HeLa, and MCF-7) were performed. Compounds 14-19, 21, 34, 31, and 30 demonstrated significant antibacterial activities with MIC values of 15.625 μg/ml. Compounds 29 and 34 were more cytotoxic than ursolic acid, with IC 50 values of 46.99 and 48.18 μg/ml. Compounds 29 and 34 in the docking studies presented favourable binding interactions and better docking energy against the Epidermal Growth Factor Receptor (EGFR) than the parent compound, ursolic acid. The findings revealed that the ursolic acid scaffold is a promising precursor for the development of molecules with promising anticancer and antimicrobial activities. However, more studies are needed to fully understand their mode of action.

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Synthesis, Biological Evaluation, Molecular Docking, and Acid Dissociation Constant of New Bis‐1,2,3‐triazole Compounds

et al. 2021

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In this study, new bis-1,2,3-triazole derivatives, N,N'-(1,3phenylene)bis(2-(4-R-1H-1,2,3-triazol-1-yl)acetamide), were synthesized by copper-catalyzed azide-alkyne cycloaddition click chemistry in 84-96 % yield. A wide range bioactivity screening was performed to determine DNA cleavage, antioxidant, antibacterial and antifungal activities. All of the synthesized bis-1,2,3-triazoles showed excellent DNA cleavage activity and 4 e, bearing 2-bromoethyl moiety as a substituent, was almost degraded all of the plasmid DNA. Molecular docking simulations suggest that the synthesized compounds act as minor groove binders of DNA. The antioxidant activities of the bis-1,2,3-triazoles were determined based on the radical scavenging effect of the stable 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical and iron chelating activity. The compounds exhibited effective iron chelating activity at 200 mg/L while showing a moderate ability to scavenge DPPH radical. The compounds exhibited antibacterial activity against B. cereus, L. pneumophila subsp. pneumophila, S. aureus, P. aeruginosa, E. coli and E. hirae bacterial strains, and antifungal activity against C. albicans and C. tropicalis microfungus strains with a MIC value in the range of 4-128 μg/mL. 4 d, bearing cyclohexylmethyl moiety as substituent, exhibited a broadspectrum antimicrobial activity (both antibacterial and antifungal). Four different acid dissociation constant (pK a ) values of each product were determined potentiometrically in 20 % (v/v) dimethyl sulfoxide-water at 25 � 0.1°C, at an ionic background of 0.1mol/L of NaCl using the HYPERQUAD program.

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Organocatalysis in the Synthesis of 1,2,3‐Triazoyl‐zidovudine Derivatives: Synthesis and Preliminary Antioxidant Activity

Cited by 8 publications

References 67 publications

Exploring the antioxidant potential of chalcogen-indolizines throughout in vitro assays

Exploring the antioxidant potential of chalcogen-indolizines throughout in vitro assays

Synthesis of Ester‐Linked Ursolic Acid‐Based Hybrid Compounds: Potential Antibacterial and Anticancer Agents

Synthesis, Biological Evaluation, Molecular Docking, and Acid Dissociation Constant of New Bis‐1,2,3‐triazole Compounds

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