Synthesis of new 2-aminocarbohydrate-1,4-naphthoquinone derivatives promoted by ultrasonic irradiation

Franco, Caroline; Jordão, Alessandro K.; Ferreira, Vı́tor F.; Pinto, Ângelo C.; Souza, Maria Cecília B. V. de; Resende, Jackson Antônio Lamounier Camargos; Cunha, Anna C.

doi:10.1590/s0103-50532011000100026

Cited by 3 publications

(4 citation statements)

References 29 publications

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“…13 In particular, aminoquinone frameworks show different activities, acting as antitumoral, antimicrobial, antimalarial, antifungal and molluscicidal. [14][15][16][17][18] Quinones exert their biological effects via quinonehydroquinone redox cycling, leading to reactive oxygen species (ROS) generation, such as superoxide anion radical (O 2 •−…”

Section: Introductionmentioning

confidence: 99%

“…[3][4][5] Aminoquinone derivatives have also been used as a potential building block for the synthesis of bioactive modified quinones. 14,15,19 Several computational and structural X-ray diffraction studies, 18,[23][24][25] in search for quantitative three-dimensional correlation structure-property (3D-QSAR) 26 have aided in the comprehension of these biological applications. The evaluation of the importance of intramolecular electronic properties, such as parameters highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energies, hardness, atomic charges, dipole moment, polarizability, molecular volume and Gibbs free energy, can provide indications of potential target molecules.…”

Section: Introductionmentioning

confidence: 99%

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Theoretical and Experimental Spectroscopic Study on 2-Chloro-3-(substitutedphenylamino)-1,4-naphthoquinone Derivatives

Dias¹,

Campos²,

Moraes³

et al. 2023

J. Braz. Chem. Soc.

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The 1,4-naphthoquinones are an important group of compounds intensively studied because of their wide range of biological activities. Four 2-chloro-3-(substituted-phenylamino)- 1,4‑naphthoquinone derivatives were synthesized, and the vibrational modes of these molecules were assigned using Raman and Fourier transform infrared spectroscopy (FTIR) techniques. In addition, X-ray studies were performed for one of these derivatives. Density functional theory (DFT) calculations were also developed for these compounds and presented. In summary, the results obtained from these studies can assess chemical changes in the structures of functionalized quinones and the discovery of candidate biologically active compounds.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Theoretical and Experimental Spectroscopic Study on 2-Chloro-3-(substitutedphenylamino)-1,4-naphthoquinone Derivatives

Dias¹,

Campos²,

Moraes³

et al. 2023

J. Braz. Chem. Soc.

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“…The synthesis of the compounds LACBio1 and LACBio2 involved the reaction of halo-naphthoquinones containing a carbonyl group with amino carbohydrates. The compounds LACBio3 and LACBio4 ( Scheme 1 ) were prepared by a cerium(IV)-mediated oxidative free radical cyclization reaction between 1,4-amino-naphthoquinones, which possess an aminocarbohydrate chain at the C-2 position of the quinone ring, and ethyl acetoacetate [ 36 ].…”

Section: Methodsmentioning

confidence: 99%

Benzo[f]indole-4,9-dione Derivatives Effectively Inhibit the Growth of Triple-Negative Breast Cancer

et al. 2021

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Triple-negative breast cancer (TNBC) is a subtype of breast cancer with poor clinical outcome, and currently no effective targeted therapies are available. Indole compounds have been shown to have potential antitumor activity against various cancer cells. In the present study, we found that new four benzo[f]indole-4,9-dione derivatives reduce TNBC cell viability by reactive oxygen species (ROS) accumulation stress in vitro. Further analyses showed that LACBio1, LACBio2, LACBio3 and LACBio4 exert cytotoxic effects on MDA-MB 231 cancer cell line by inducing the intrinsic apoptosis pathway, activating caspase 9 and Bax/Bcl-2 pathway in vitro. These results provide evidence that these new four benzo[f]indole-4,9-dione derivatives could be potential therapeutic agents against TNBC by promoting ROS stress-mediated apoptosis through intrinsic-pathway caspase activation.

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“…Naphthoquinones are biologically important compounds, mainly due to their pharmacological potential and cytotoxicity (Villamil et al, 1996). The molecular structures of these substances allow them to be used in vital biochemical processes (Moura et al, 2001), which has contributed to an increase in studies related to their biological actions (Franco et al, 2011).…”

Section: Naphthoquinones and The Tabebuia Genusmentioning

confidence: 99%

Anti-inflammatory and cicatrizing properties of the Tabebuia genus: A review

Brito

Pereira

Silva

et al. 2021

RSD

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The Tabebuia genus is one of the largest genera of the Bignoniaceae family, comprising more than 100 species. One of its main representatives is the ipê tree, which is popularly known for their ornamental and logging potential. However, parts of the tree, such as the stem, leaves and flowers, are used in traditional medicine for anti-bacterial, anti-inflammatory (rhinitis, sinusitis, tonsillitis and pharyngitis), anti-ulcerogenic, antiviral, antineoplastic, antimalarial and immunomodulatory purposes. The objective of the present study was to collate articles on the cicatrizing and therapeutic properties of species belonging to the Tabebuia spp genus.

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Synthesis of new 2-aminocarbohydrate-1,4-naphthoquinone derivatives promoted by ultrasonic irradiation

Cited by 3 publications

References 29 publications

Theoretical and Experimental Spectroscopic Study on 2-Chloro-3-(substitutedphenylamino)-1,4-naphthoquinone Derivatives

Theoretical and Experimental Spectroscopic Study on 2-Chloro-3-(substitutedphenylamino)-1,4-naphthoquinone Derivatives

Benzo[f]indole-4,9-dione Derivatives Effectively Inhibit the Growth of Triple-Negative Breast Cancer

Anti-inflammatory and cicatrizing properties of the Tabebuia genus: A review

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