Synthesis of Carvone-Derived 1,2,3-Triazoles Study of Their Antioxidant Properties and Interaction with Bovine Serum Albumin

Galstyan, A. S.; Martiryan, Armen I.; Grigoryan, K. R.; Ghazaryan, Armine G.; Samvelyan, M. A.; Ghochikyan, Tariel V.; Nenajdenko, Valentine G.

doi:10.3390/molecules23112991

Cited by 22 publications

(15 citation statements)

References 36 publications

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“…The data demonstrate that a reaction in THF allowed the preparation of compound 2, providing the highest yield of 70%. Triplets at 2.47 (CH 2 CO) and 3.20 (NHCH 2 ), the singlet at 3.77 (NHCH 2 ), and a broad singlet at 11.81 (COOH) in 1 H NMR for the compound confirmed the formation of the β-alanine fragment in the structure.…”

Section: Synthesis Of Novel Aminothiazolesmentioning

confidence: 75%

“…FT-IR spectra (ν, cm −1 ) were recorded on a Perkin-Elmer Spectrum BX FT-IR spectrometer (Perkin-Elmer Inc., Waltham, MA, USA) using KBr pellets. 1 H and 13 C-NMR spectra were recorded in DMSO-d 6 on a Bruker Avance III (400 MHz, 101 MHz and 700 MHz, 176 MHz) spectrometer. Chemical shifts (δ) are reported in parts per million (ppm) calibrated from TMS (0 ppm) as an internal standard for 1 H-NMR and DMSO-d 6 (39.43 ppm) for 13 C-NMR.…”

Section: Synthesis Of Novel Compoundsmentioning

confidence: 99%

“…Progress in organic and medicinal chemistry allows for the design, synthesis and optimization of the structures of novel thiazole compounds. Thiazole compounds are widely used in the pharmaceutical industry for the design of therapeutics and novel biosensors for their antioxidant [ 1 , 2 , 3 ], antibacterial [ 4 , 5 , 6 ], anti-proliferative [ 7 ], antiparasitic [ 8 ], anti-inflammatory [ 9 ], analgesic [ 10 ], neuroprotective [ 11 ], antiviral (including SARS-CoV-2) [ 12 ], and anti-HIV activities [ 13 ]. Studies of thiazole-structure activities promote the improvement of their chemical/biochemical and therapeutic properties and anti-TB activity, mainly against resistant Mycobacterium tuberculosis (Mtb) strains [ 14 ].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Novel Aminothiazole Derivatives as Promising Antiviral, Antioxidant and Antibacterial Candidates

Minickaitė

Grybaitė

Vaickelionienė

et al. 2022

IJMS

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It is well-known that thiazole derivatives are usually found in lead structures, which demonstrate a wide range of pharmacological effects. The aim of this research was to explore the antiviral, antioxidant, and antibacterial activities of novel, substituted thiazole compounds and to find potential agents that could have biological activities in one single biomolecule. A series of novel aminothiazoles were synthesized, and their biological activity was characterized. The obtained results were compared with those of the standard antiviral, antioxidant, antibacterial and anticancer agents. The compound bearing 4-cianophenyl substituent in the thiazole ring demonstrated the highest cytotoxic properties by decreasing the A549 viability to 87.2%. The compound bearing 4-trifluoromethylphenyl substituent in the thiazole ring showed significant antiviral activity against the PR8 influenza A strain, which was comparable to the oseltamivir and amantadine. Novel compounds with 4-chlorophenyl, 4-trifluoromethylphenyl, phenyl, 4-fluorophenyl, and 4-cianophenyl substituents in the thiazole ring demonstrated antioxidant activity by DPPH, reducing power, FRAP methods, and antibacterial activity against Escherichia coli and Bacillus subtilis bacteria. These data demonstrate that substituted aminothiazole derivatives are promising scaffolds for further optimization and development of new compounds with potential influenza A-targeted antiviral activity. Study results could demonstrate that structure optimization of novel aminothiazole compounds may be useful in the prevention of reactive oxygen species and developing new specifically targeted antioxidant and antibacterial agents.

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Section: Synthesis Of Novel Aminothiazolesmentioning

confidence: 75%

Section: Synthesis Of Novel Compoundsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of Novel Aminothiazole Derivatives as Promising Antiviral, Antioxidant and Antibacterial Candidates

Minickaitė

Grybaitė

Vaickelionienė

et al. 2022

IJMS

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“…Carvone also caused the scavenging of the DPPH radical and the reduction of molybdenum, Mo(VI) to Mo(V). Galstyan et al [ 84 ] documented the antioxidant property of a synthesis of carvone-derived 1,2,3-triazoles. The conjugates prepared demonstrated high antioxidant activity.…”

Section: Resultsmentioning

confidence: 99%

Health Benefits and Pharmacological Properties of Carvone

et al. 2021

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Carvone is a monoterpene ketone contained in the essential oils of several aromatic and medicinal plants of the Lamiaceae and Asteraceae families. From aromatic plants, this monoterpene is secreted at different concentrations depending on the species, the parts used, and the extraction methods. Currently, pharmacological investigations showed that carvone exhibits multiple pharmacological properties such as antibacterial, antifungal, antiparasitic, antineuraminidase, antioxidant, anti-inflammatory, and anticancer activities. These studies were carried out in vitro and in vivo and involved a great deal of knowledge on the mechanisms of action. Indeed, the antimicrobial effects are related to the action of carvone on the cell membrane and to ultrastructural changes, while the anti-inflammatory, antidiabetic, and anticancer effects involve the action on cellular and molecular targets such as inducing of apoptosis, autophagy, and senescence. With its multiple mechanisms, carvone can be considered as natural compounds to develop therapeutic drugs. However, other investigations regarding its precise mechanisms of action as well as its acute and chronic toxicities are needed to validate its applications. Therefore, this review discusses the principal studies investigating the pharmacological properties of carvone, and the mechanism of action underlying some of these properties. Moreover, further investigations of major pharmacodynamic and pharmacokinetic studies were also suggested.

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“…According to our previous work in collaboration, 1,2,3-triazoles obtained using triazole 5 displayed pronounced antioxidant and fluorescent properties. 32 Scheme 2. Synthesis of (R)-5-(3-azido-prop-1-en-2-yl)-2-methylcyclohex-2-enone 5.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of novel 1,2,3-triazole-based hybrids via click reactions

Sirakanyan¹,

Ghochikyan²,

Spinelli³

et al. 2021

Arkivoc

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1,2,3-Triazoles have attracted the interest of researchers due to their wide range of biological activities which include antitumor, anti-leishmanial, bioluminescent and fungicidal activities This paper describes the synthesis of novel triazole hybrids containing biologically active fragments through cycloaddition (click) reactions, with the aim of increasing the diversity of known and active 1,2,3-triazole derivatives. All new compounds have been characterized by physicochemical methods.

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Synthesis of Carvone-Derived 1,2,3-Triazoles Study of Their Antioxidant Properties and Interaction with Bovine Serum Albumin

Cited by 22 publications

References 36 publications

Synthesis of Novel Aminothiazole Derivatives as Promising Antiviral, Antioxidant and Antibacterial Candidates

Synthesis of Novel Aminothiazole Derivatives as Promising Antiviral, Antioxidant and Antibacterial Candidates

Health Benefits and Pharmacological Properties of Carvone

Synthesis of novel 1,2,3-triazole-based hybrids via click reactions

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