Synthesis, Antitumor Activity and Docking of 2,3-(Substituted)-1,4-Naphthoquinone Derivatives Containing Nitrogen, Oxygen and Sulfur

Delarmelina, Maicon; Daltoé, Renata Dalmaschio; Cerri, Murilo F.; Madeira, Klesia Pirola; Rangel, L.B.A.; Júnior, Valdemar Lacerda; Romão, Wanderson; Taranto, Alex Gutterres; Greco, Sandro J.

doi:10.5935/0103-5053.20150157

Cited by 22 publications

(20 citation statements)

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“…Surprisingly, the reaction time when water is used as the solvent (entry 2) is drastically reduced considering the other solvents. In a recent work of our research group, 49 we discussed the preparation of 1,4-naphthoquinonic derivatives in aqueous media and its effects: it is possible that, since the compounds are hydrophobic, the frequency of effective collisions is enhanced once they are repelled by water molecules and forced to approach (hydrophobic effect), resulting in the diminish of reaction time due to statistical reasons.…”

Section: Chemical Resultsmentioning

confidence: 99%

“…Once the electrophilic intermediate 10 was synthesized, compound 11 (the nucleophile to obtain the molecular hybrid 3) was prepared following a procedure described by our research group earlier ( Figure 10). 49 In the following step, the target molecular hybrid 3 was obtained with yield of 47% in 16 h ( Figure 10). The synthesis of the molecular hybrids 2 and 3 follows the same mechanistic purpose: a nucleophilic aromatic substitution.…”

Section: Chemical Resultsmentioning

confidence: 99%

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Synthesis, Molecular Modelling and Anticancer Activities of New Molecular Hybrids Containing 1,4-Naphthoquinone, 7-Chloroquinoline, 1,3,5-Triazine and Morpholine Cores as PI3K and AMPK Inhibitors in the Metastatic Melanoma Cells

Fiorot

Westphal

Lemos

et al. 2019

J. Braz. Chem. Soc.

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Three molecular hybrids containing 1,4-naphthoquinones, 1,3,5-triazines, morpholine and 7-chloroquinoline, which have recognized contributions to the biological activity of many drugs, were synthesized in yields ranging from 43-84%. All hybrids were obtained in three steps starting from readily available reactants: lawsone, cyanuric chloride, morpholine and 4,7-dichloroquinoline. A previous docking study was carried out to identify the binding energy and pharmacophore conformation of the promising anticancer compounds with PI3Kγ (phosphoinositide 3-kinase) and AMPK (5' AMP-activated protein kinase). The cancer activity in human metastatic melanoma cells (SKMEL-103) were performed, and the synthetized compounds presented half maximal inhibitory concentration (IC 50) values around 25 μM. The expressions of PI3K and AMPK were also determined using western blotting technique, and all molecular hybrids negatively modulated both targets.

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Section: Chemical Resultsmentioning

confidence: 99%

Section: Chemical Resultsmentioning

confidence: 99%

Synthesis, Molecular Modelling and Anticancer Activities of New Molecular Hybrids Containing 1,4-Naphthoquinone, 7-Chloroquinoline, 1,3,5-Triazine and Morpholine Cores as PI3K and AMPK Inhibitors in the Metastatic Melanoma Cells

Fiorot

Westphal

Lemos

et al. 2019

J. Braz. Chem. Soc.

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“…1,4‐Naphthoquinone ( 1a ) was purified via reduced pressure sublimation using a cold finger sublimation apparatus (50 °C, 0.9 mbar) and stored in a glovebox to prevent contact with moisture. Starting materials 1 were prepared following previously methods described in the literature , . Other chemicals were obtained from commercial sources and used without further purification.…”

Section: Methodsmentioning

confidence: 99%

Ruthenium(II)‐Catalyzed C–H Alkenylation of Quinones: Diversity‐Oriented Strategy for Trypanocidal Compounds

et al. 2019

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Ruthenium(II)‐catalysis enabled C–H alkenylations of unactivated naphthoquinones for the preparation of A‐ring‐modified naphthoquinoidal compounds with activity against Trypanosoma cruzi, the parasite causing Chagas disease. The present study encompasses C–H alkenylation by weak O‐coordination by means of ruthenium(II) carboxylates. This method provided an efficient and versatile tool towards a diversity‐oriented strategy for the preparation of compounds with a relevant biological profile.

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“…They are structurally related to naphthalene, with carbonyl groups being substituted at the 1,4 or 1,2 positions. The 1,4-naphthoquinones are known for their broad biological activity, including antitumor and antiproliferative, 1,2 antimicrobial, [3][4][5] and anti-inflammatory. 6 The biological activity of naphthoquinones is generally related to a redox process of the quinone system, which may lead to the formation of reactive oxygen species (ROS).…”

Section: Introductionmentioning

confidence: 99%

Antibacterial Activity of 2-Amino-1,4-naphthoquinone Derivatives Against Gram‑Positive and Gram-Negative Bacterial Strains and Their Interaction with Human Serum Albumin

Silva

Chaves

Paiva

et al. 2020

J. Braz. Chem. Soc.

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A series of 2-amino-1,4-naphthoquinone derivatives (NQA-NQF) was synthesized by alternative methods (ultrasonication and microwave irradiation), with yields ranging from 40 to 71%, and without the need of further recrystallization. Each compound was evaluated against four Gram-positive (Bacillus subtilis, Enterococcus faecalis, Staphylococcus aureus and Bacillus cereus) and five Gram-negative (Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Acinetobacter baumannii and Klebsiella pneumoniae positive β-lactamase) bacteria strains. The NQF was the most active amino-naphthoquinone derivative with minimum inhibitory concentration (MIC) of 31.2 µg mL-1 against K. pneumoniae positive β-lactamase (a common intestinal bacteria which can cause life-threatening infections). On the other hand, NQA and NQC showed good activity as a potential antibiotic for the bacteria strains assayed, except for K. pneumoniae. In addition, the affinity of these three most active compounds (NQA, NQC, and NQF) for human serum albumin (HSA) was evaluated employing multiple spectroscopic techniques (steady-state, time-resolved, and synchronous fluorescence, as well as circular dichroism), combined with theoretical calculations (molecular docking). The interaction HSA:2-amino-1,4-naphthoquinones occurs spontaneously and moderately inside the subdomain IIA (Sudlow's site I) via hydrogen bonding and van der Waals forces.

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Synthesis, Antitumor Activity and Docking of 2,3-(Substituted)-1,4-Naphthoquinone Derivatives Containing Nitrogen, Oxygen and Sulfur

Cited by 22 publications

References 1 publication

Synthesis, Molecular Modelling and Anticancer Activities of New Molecular Hybrids Containing 1,4-Naphthoquinone, 7-Chloroquinoline, 1,3,5-Triazine and Morpholine Cores as PI3K and AMPK Inhibitors in the Metastatic Melanoma Cells

Synthesis, Molecular Modelling and Anticancer Activities of New Molecular Hybrids Containing 1,4-Naphthoquinone, 7-Chloroquinoline, 1,3,5-Triazine and Morpholine Cores as PI3K and AMPK Inhibitors in the Metastatic Melanoma Cells

Ruthenium(II)‐Catalyzed C–H Alkenylation of Quinones: Diversity‐Oriented Strategy for Trypanocidal Compounds

Antibacterial Activity of 2-Amino-1,4-naphthoquinone Derivatives Against Gram‑Positive and Gram-Negative Bacterial Strains and Their Interaction with Human Serum Albumin

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