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Journal articles on the topic 'Naphthoquinone'

Author: Grafiati

Published: 4 June 2021

Last updated: 26 July 2025

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1

Córdova-Rivas, Sergio, Jorge Gustavo Araujo-Huitrado, Ernesto Rivera-Avalos, et al. "Differential Proliferation Effect of the Newly Synthesized Valine, Tyrosine and Tryptophan–Naphthoquinones in Immortal and Tumorigenic Cervical Cell Lines." Molecules 25, no. 9 (2020): 2058. http://dx.doi.org/10.3390/molecules25092058.

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We previously showed that microwave assisted synthesis is the best method for the synthesis of naphthoquinone amino acid and chloride-naphthoquinone amino acid derivatives by a complete evaluation of reaction conditions such as stoichiometry, bases, and pH influence. Following the same strategy, we synthesized chloride and non-chloride tyrosine, valine, and tryptophan-naphthoquinones achieving 85–95%, 80–92%, and 91–95% yields, respectively. The cyclic voltammetry profiles showed that both series of naphthoquinone amino acid derivatives mainly display one redox reaction process. Overall, chlor

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2

Buffinton, G. D., K. Öllinger, A. Brunmark, and E. Cadenas. "DT-diaphorase-catalysed reduction of 1,4-naphthoquinone derivatives and glutathionyl-quinone conjugates. Effect of substituents on autoxidation rates." Biochemical Journal 257, no. 2 (1989): 561–71. http://dx.doi.org/10.1042/bj2570561.

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DT-diaphorase catalysed the reduction of 1,4-naphthoquinones with hydroxy, methyl, methoxy and glutathionyl substituents at the expense of reducing equivalents from NADPH. The initial rates of quinone reduction did not correlate with either the half-wave reduction potential (E1/2) value (determined by h.p.l.c. with electrochemical detection against an Ag/AgCl reference electrode) or the partition coefficient of the quinones. After their reduction by DT-diaphorase the 1,4-naphthoquinone derivatives autoxidized at distinct rates, the extent of which was influenced by the nature of the substituen

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3

Liu, Rui, and Hong Li. "Structural Modification of 1,4-Naphthoquinone Molecule for Application in Dyeing." Advanced Materials Research 781-784 (September 2013): 979–82. http://dx.doi.org/10.4028/www.scientific.net/amr.781-784.979.

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Quinones are useful compounds as dye compounds and the 1,4-naphthoquinone structure constitutes an essential part of these classes of compounds. The process in constructing 1,4-naphthoquinone for possible screening as dyestuff is described, starting from 1,4-naphthoquinone and hydroxy acid. It provides a novel methodology for the synthesis of the 5-nitro-2-substituted 1,4-naphthoquinones. The products were characterized by IR and1H NMR.

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Rudnicka, Małgorzata, Michał Ludynia, and Waldemar Karcz. "Effects of Naphthazarin (DHNQ) Combined with Lawsone (NQ-2-OH) or 1,4-Naphthoquinone (NQ) on the Auxin-Induced Growth of Zea mays L. Coleoptile Segments." International Journal of Molecular Sciences 20, no. 7 (2019): 1788. http://dx.doi.org/10.3390/ijms20071788.

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Naphthoquinones, plants secondary metabolites are known for their antibacterial, antifungal, anti-inflammatory, anti-cancer and anti-parasitic properties. The biological activity of naphthoquinones is connected with their ability to generate reactive oxygen species and to modify biological molecules at their nucleophilic sites. In our research, the effect of naphthazarin (DHNQ) combined with 2-hydroxy-1,4-naphthoquinone (NQ-2-OH) or 1,4-naphthoquinone (1,4-NQ) on the elongation growth, pH changes of the incubation medium, oxidative stress and redox activity of maize coleoptile cells were inves

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5

Ma, Qinge, Rongrui Wei, and Zhipei Sang. "Structural Characterization and Hepatoprotective Activity of Naphthoquinone From Cucumis bisexualis." Natural Product Communications 15, no. 1 (2020): 1934578X2090289. http://dx.doi.org/10.1177/1934578x20902898.

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Three new naphthoquinones, namely 5,8-dihydroxy-7′-isopropyl-furan ring-1″-prenyl-naphthoquinone (1), 5,8-dihydroxy-7′-propenyl-furan ring-1″-isopropanol-naphthoquinone (2), and 5,8-dihydroxy-7′-isopropanol-furan ring-1″-(5″-hydroxyphenyl)-naphthoquinone (3), along with 10 known naphthoquinone derivatives (4-13) were isolated from Cucumis bisexualis for the first time. All the compounds were elucidated on the basis of spectroscopic data analysis and chemical evidence. Compounds (1-13) were evaluated for their hepatoprotective activites on human L-O2 cells. Among them, compounds 1, 4, and 8 exh

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6

Rivera-Ávalos, Ernesto, Denisse de Loera, Jorge Gustavo Araujo-Huitrado, et al. "Synthesis of Amino Acid–Naphthoquinones and In Vitro Studies on Cervical and Breast Cell Lines." Molecules 24, no. 23 (2019): 4285. http://dx.doi.org/10.3390/molecules24234285.

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We performed an extensive analysis about the reaction conditions of the 1,4-Michael addition of amino acids to 1,4-naphthoquinone and substitution to 2,3-dichloronaphthoquinone, and a complete evaluation of stoichiometry, use of different bases, and the pH influence was performed. We were able to show that microwave-assisted synthesis is the best method for the synthesis of naphthoquinone–amino acid and chloride–naphthoquinone–amino acid derivatives with 79–91% and 78–91% yields, respectively. The cyclic voltammetry profiles showed that both series of naphthoquinone–amino acid derivatives main

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7

Ríos, David, Jaime A. Valderrama, Miriam Cautin, et al. "New 2-Acetyl-3-aminophenyl-1,4-naphthoquinones: Synthesis and In Vitro Antiproliferative Activities on Breast and Prostate Human Cancer Cells." Oxidative Medicine and Cellular Longevity 2020 (September 26, 2020): 1–11. http://dx.doi.org/10.1155/2020/8939716.

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The reaction of 2-acyl-1,4-naphthoquinones with N,N-dimethylaniline and 2,5-dimethoxyaniline, promoted by catalytic amounts of CeCl3·7H2O under “open-flask” conditions, produced a variety of 2-acyl-3-aminophenyl-1,4-naphthoquinones structurally related to the cytotoxic 2-acetyl-3-phenyl-1,4-naphthoquinone, an inhibitor of the heat shock chaperone protein Hsp90. The members of the 2-acyl-3-aminophenyl-1,4-naphthoquinone series were isolated in good yields (63-98%). The cyclic voltammograms of the 2-acyl-3-aminophenyl-1,4-naphthoquinone exhibit two one-electron reduction waves to the correspondi

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8

Kumbhar, A. S., S. B. Padhye, Jitender, and R. K. Kale. "Naturally Occurring Hydroxy Napthoquinones and Their Iron Complexes as Modulators of Radiation Induced Lipid Peroxidation in Synaptosomes." Metal-Based Drugs 4, no. 5 (1997): 279–85. http://dx.doi.org/10.1155/mbd.1997.279.

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The modulation of radiation induced lipid peroxidation in synaptosomes by iron (II) and iron (III) complexes of two naturally occurring and therapeutically relevant naphthoquinones viz. 5,hydroxy-1,4 naphthoquinone; juglone and 2,hydroxy-1,4 naphthoquinone; lawsone, have been studied. At lower concentrations the complexes enhance lipid peroxidation predominantly through redox cycling as observed for Fe(II)- juglonate while at higher concentrations the complexes tend to limit lipid peroxidation through fast recombinations.

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9

Raspotnig, Günther, Felix Anderl, and Ronald M. Clouse. "The scent gland chemistry of neogoveid cyphophthalmids (Opiliones): an unusual methyljuglone from Metasiro savannahensis." Chemoecology 29, no. 5-6 (2019): 189–97. http://dx.doi.org/10.1007/s00049-019-00288-y.

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Abstract While the chemistries of scent gland secretions from a few selected species of three families of Cyphophthalmi, namely Sironidae, Pettalidae, and Stylocellidae, have already been reported and found to consist of complex blends of naphthoquinones and methyl ketones, nothing is known about the other families. We here report on the secretions of Metasiro savannahensis Clouse and Wheeler (Zootaxa 3814:177–201, 2014), a first representative of the family Neogoveidae. The secretions from males, females and one juvenile were extracted and analyzed by gas chromatography–mass spectrometry. Twe

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10

Saralaya, Sanjay Sukumar, and Shridhara Kanakamajalu. "A Systematic Exfoliation of Prior Arts About The Use of Natural and Synthesized 1,4-Naphthoquinones Towards Corrosion Inhibition." Walisongo Journal of Chemistry 7, no. 2 (2024): 143–67. https://doi.org/10.21580/wjc.v7i2.22657.

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In this review segment, use of natural and synthesized 1,4-naphthoquinones for corrosion inhibition was comprehensively covered based on the past research disclosures. The prior arts were gathered from various research article repositories by the use of search terms like ‘Quinonoids as corrosion inhibitors’ and ‘1,4-Napthoquinones as corrosion inhibitors’ as a part of direct referencing. Additionally, back and cross referencing were also done to ensure the complete collection of prior arts. This work will help the researchers to understand the credibility of 1,4-naphthoquinones as corrosion in

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11

de Souza, Acácio S., Ruan Carlos B. Ribeiro, Dora C. S. Costa, et al. "Menadione: a platform and a target to valuable compounds synthesis." Beilstein Journal of Organic Chemistry 18 (April 11, 2022): 381–419. http://dx.doi.org/10.3762/bjoc.18.43.

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Naphthoquinones are important natural or synthetic compounds belonging to the general class of quinones. Many compounds in this class have become drugs that are on the pharmaceutical market for the treatment of various diseases. A special naphthoquinone derivative is menadione, a synthetic naphthoquinone belonging to the vitamin K group. This compound can be synthesized by different methods and it has a broad range of biological and synthetic applications, which will be highlighted in this review.

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12

Mercier, Alexis, Alizée Monet, Madyan A. Yaseen, M. Iris Hermanns, and Michael Oelgemöller. "Synthesis of Acylated Naphthohydroquinones Through Photo-Friedel–Crafts Acylation and Evaluation of Their Antibiotic Potential." Photochem 4, no. 4 (2024): 501–10. https://doi.org/10.3390/photochem4040031.

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A variety of 1-(1,4-dihydroxynaphtalen-2-yl) ketones was synthesized using the photo-Friedel–Crafts acylation of 1,4-naphthoquinone with aldehydes. Subsequent oxidation using silver oxide readily furnished the corresponding 2-acylated 1,4 naphthoquinones. Notably, these naphthoquinone derivatives underwent spontaneous partial reduction upon storage. The synthesized compounds were subjected to antimicrobial screening. High inhibition effects on Staphylococcus aureus were found for the majority of compounds, which makes them interesting for potential future medicinal applications.

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13

Zeng, Fan-Lin, Xiao-Lan Chen, Shuai-Qi He, et al. "Copper-catalyzed one-pot three-component thioamination of 1,4-naphthoquinone." Organic Chemistry Frontiers 6, no. 9 (2019): 1476–80. http://dx.doi.org/10.1039/c9qo00091g.

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14

Valderrama, Jaime A., Mónica Cabrera, Julio Benites, et al. "Synthetic approaches and in vitro cytotoxic evaluation of 2-acyl-3-(3,4,5-trimethoxyanilino)-1,4-naphthoquinones." RSC Advances 7, no. 40 (2017): 24813–21. http://dx.doi.org/10.1039/c7ra03238b.

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2-Acyl-1,4-naphthoquinones react with 3,4,5-trimethoxyaniline, under aerobic conditions, to give benzophenanthridinequinone, benzocarbazole and 2-acyl-3-(3,4,5-trimethoxyanilino)-1,4-naphthoquinone derivatives.

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15

Rakesh, Kumar Sahu, Kumari Khushbu, Kumari Pooja, et al. "A Review on Properties and Pharmacological Activity of Naphthoquinone and its Derivatives." Chemistry Research Journal 10, no. 2 (2025): 87–94. https://doi.org/10.5281/zenodo.15606076.

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Naphthoquinone forms the central chemical structure of many natural compounds, most notably the K Vitamins. 2-Methylnaphthoquinone is a more effective coagulant than vitamin K. Naphthoquinone derivatives are cytotoxic, they have significant antibacterial, antifungal, antiviral, insecticidal, anti-inflammatory, and antipyretic properties. Quinone derivatives may be toxic to cells by a number of mechanisms including redox cycling, arylation, intercalation, induction of DNA strands breaks, generation of free radicals and alkylation via quinone methide formation. 5-Hydroxy-1, 4-naphthoquinone, jug

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16

Medina, L. F. C., P. F. Hertz, V. Stefani, J. A. P. Henriques, A. Zanotto-Filho, and A. Brandelli. "Aminonaphthoquinone induces oxidative stress inStaphylococcus aureus." Biochemistry and Cell Biology 84, no. 5 (2006): 720–27. http://dx.doi.org/10.1139/o06-087.

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The biological activity of 5-amino-8-hydroxy-1,4-naphthoquinone (ANQ) on Staphylococcus aureus was investigated in comparison with the unsubstituted 1,4-naphthoquinone (NQ). Complete inhibition of microbial growth was observed with ANQ and NQ at 50 and 10 µg/mL, respectively. The antibacterial effect of naphthoquinones decreased in the presence of sodium ascorbate, but the superoxide scavenger 4,5-dihydroxy-1,3-benzene-disulfonic acid (Tiron) was able to protect S. aureus only from the harmful effect of ANQ. Naphthoquinones blocked oxygen uptake and induced cyanide-insensitive oxygen consumpti

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17

Navarro-Tovar, Gabriela, Sarai Vega-Rodríguez, Elisa Leyva, Silvia Loredo-Carrillo, Denisse de Loera, and Lluvia Itzel López-López. "The Relevance and Insights on 1,4-Naphthoquinones as Antimicrobial and Antitumoral Molecules: A Systematic Review." Pharmaceuticals 16, no. 4 (2023): 496. http://dx.doi.org/10.3390/ph16040496.

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Natural product derivatives are essential in searching for compounds with important chemical, biological, and medical applications. Naphthoquinones are secondary metabolites found in plants and are used in traditional medicine to treat diverse human diseases. Considering this, the synthesis of naphthoquinone derivatives has been explored to contain compounds with potential biological activity. It has been reported that the chemical modification of naphthoquinones improves their pharmacological properties by introducing amines, amino acids, furan, pyran, pyrazole, triazole, indole, among other

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18

Vaverkova, Veronika, Oldrich Vrana, Vojtech Adam, Tomas Pekarek, Josef Jampilek, and Petr Babula. "The Study of Naphthoquinones and Their Complexes with DNA by Using Raman Spectroscopy and Surface Enhanced Raman Spectroscopy: New Insight into Interactions of DNA with Plant Secondary Metabolites." BioMed Research International 2014 (2014): 1–12. http://dx.doi.org/10.1155/2014/461393.

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Naphthoquinones represent the group of plant secondary metabolites with cytotoxic properties based on their ability to generate reactive oxygen species and interfere with the processes of cell respiration. Due to this fact, the possible cytotoxic mechanisms on cellular and subcellular levels are investigated intensively. There are many targets of cytotoxic action on the cellular level; however, DNA is a critical target of many cytotoxic compounds. Due to the cytotoxic properties of naphthoquinones, it is necessary to study the processes of naphthoquinones, DNA interactions (1,4-naphthoquinone,

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19

Ball, M. D., M. S. Bartlett, M. Shaw, J. W. Smith, M. Nasr, and S. R. Meshnick. "Activities and Conformational Fitting of 1,4-Naphthoquinone Derivatives and Other Cyclic 1,4-Diones Tested In Vitro against Pneumocystis carinii." Antimicrobial Agents and Chemotherapy 45, no. 5 (2001): 1473–79. http://dx.doi.org/10.1128/aac.45.5.1473-1479.2001.

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ABSTRACT Atovaquone is a chemotherapeutic agent used to treat pneumonia caused by Pneumocystis carinii in some immunocompromised patients. A set of cyclic 1,4-diones were tested in vitro for ability to inhibit growth of P. carinii, including 22 variously substituted 1,4-naphthoquinones, one bis-1,4-naphthoquinone, and three other quinones. For comparison, the antipneumocystic primaquine and its 5-hydroxy-6-desmethyl metabolite were also tested. At 1.0 μg/ml, seven compounds inhibited growth by at least 39%, with atovaquone at 92%; of these seven, five are 2-hydroxy-1,4-naphthoquinones, while o

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Chakraborty, Soumen, Gaurav Das, Surajit Ghosh, and Dipakranjan Mal. "Regioselective synthesis of naphthoquinone/naphthoquinol–carbohydrate hybrids by [4 + 2] anionic annulations and studies on their cytotoxicity." Organic & Biomolecular Chemistry 14, no. 45 (2016): 10636–47. http://dx.doi.org/10.1039/c6ob02154a.

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21

Molleti, Nagaraju, and Vinod K. Singh. "Highly enantioselective synthesis of naphthoquinones and pyranonaphthoquinones catalyzed by bifunctional chiral bis-squaramides." Organic & Biomolecular Chemistry 13, no. 18 (2015): 5243–54. http://dx.doi.org/10.1039/c5ob00105f.

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A variety of enantioenriched naphthoquinones has been synthesized in high yields and excellent enantioselectivities (up to >99% ee) using a bifunctional chiral bis-squaramide catalyzed conjugate addition of 2-hydroxy-1,4-naphthoquinone to 2-enoylpyridines.

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Ribeiro, Ruan Carlos B., Patricia G. Ferreira, Amanda de A. Borges, Luana da S. M. Forezi, Fernando de Carvalho da Silva, and Vitor F. Ferreira. "1,2-Naphthoquinone-4-sulfonic acid salts in organic synthesis." Beilstein Journal of Organic Chemistry 18 (January 5, 2022): 53–69. http://dx.doi.org/10.3762/bjoc.18.5.

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Several low molecular weight naphthoquinones are very useful in organic synthesis. These compounds have given rise to thousands of other naphthoquinones that have been tested against various microorganisms and pharmacological targets, including being used in the preparation of several drugs that are on the pharmaceutical market. Among these naphthoquinones, the series of compounds prepared from 1,2-naphthoquinone-4-sulfonic acid salts (β-NQS) stands out. In addition to being used in organic synthesis, they are excellent analytical derivatization reagents to spectrophotometrically determine dru

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23

Schlauer, Jan, Andreas Wistuba, Siegfried R. H. Hartmeyer, and Irmgard Hartmeyer. "The taxonomic relevance of Naphthoquinones in tropical pitcher plants (Nepenthes L., Nepenthaceae)." Carnivorous Plant Newsletter 51, no. 4 (2022): 185–93. http://dx.doi.org/10.55360/cpn514.js802.

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The distribution of the naphthoquinones ramentaceone and plumbagin was studied among 50 taxa of the genus Nepenthes. Naphthoquinone patterns support classifications based on homology of plastid and/or nuclear genes to some extent, with plumbagin predominant in sections Nepenthes, Urceolatae, Tentaculatae, and Regiae, ramentaceone predominant in sections Insignes and Villosae, and both isomers present without clear predominance in sections Pyrophytae and Montanae. Only 9 of 96 studied species contained both isomers in the same plant. Naphthoquinone data from artificial hybrids of known parentag

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Tandon, Vishnu K., Hardesh K. Maurya, Sandeep Kumar, Aijaz Rashid, and Dulal Panda. "Synthesis and evaluation of 2-heteroaryl and 2,3-diheteroaryl-1,4-naphthoquinones that potently induce apoptosis in cancer cells." RSC Adv. 4, no. 24 (2014): 12441–47. http://dx.doi.org/10.1039/c3ra47720g.

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This article describes the preparation of 2-heteroaryl and 600 dpi in TIF format)??>2,3-diheteroaryl-1,4-naphthoquinones by an environmentally benign short synthetic route with the goal of finding 1,4-naphthoquinone derivatives that induce apoptosis in cancer cells.

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Yang, Xiaojuan, and Liqiang Wu. "Synthesis of Novel 1,4-Naphthoquinones Possessing Indole Scaffolds Using In(OTf)3 in Solvent-Free Conditions." Molecules 23, no. 8 (2018): 1954. http://dx.doi.org/10.3390/molecules23081954.

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Novel 1,4-naphthoquinones possessing indole scaffolds were prepared by the reaction of 2-hydroxy-1,4-naphthoquinone-substituted salicylic aldehydes and indoles using In(OTf)3 as a catalyst. The method has the advantages of simple operation, mild reaction conditions, and friendly environment.

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Kallmayer, H. J., and M. Doerr. "Die Reaktion des 2,3,4a,8a-Tetrachlor-6,7-dimethyl-4a,5,8,8a-tetrahydro-1,4-naphthochinons mit Aminen." Scientia Pharmaceutica 68, no. 2 (2000): 129–39. http://dx.doi.org/10.3797/scipharm.aut-00-12.

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2,3,4a,8a-Tetrachloro-6,7-dimethyl-4a,5 ,8,8a-tetrahydro-1,4-naphthoquinone (5) reacts with arylamines 8a-e to give 2-amino-dihydroquinones 4a-e. Alkylamines 8f and h give 2-amino-dihydroquinones 4f, h and 2-amino-1,4-naphthoquinones 7f, h, dialkylamines 9f, g, i and j give 2-amino-dihydroqulnones 3f, g, i, j, 2-amino-1,4-naphthoquinones 6f, g, i, j and the photodesalkylated products 10f and g.

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Polonik, Sergey, Yuri Sabutskii, and Vladimir Denisenko. "The Acid-Catalyzed 2-O-Alkylation of Substituted 2-Hydroxy-1,4-naphthoquinones by Alcohols: Versatile Preparative Synthesis of Spinochrome D and Its 6-Alkoxy Derivatives." Synthesis 50, no. 18 (2018): 3738–48. http://dx.doi.org/10.1055/s-0037-1610415.

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A series of substituted 2-alkoxy-1,4-naphthoquinone derivatives were obtained by acid-catalyzed condensation of substituted 2-hydroxy-1,4-naphthoquinones with propan-1-ol, butan-1-ol, or pentan-1-ol in good yields. Based on this reaction a versatile preparative synthesis of spinochrome D was developed.

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Heneha, A., A. Tarnovska, M. Yaremchuk, A. Budevych, and O. Semochko. "The content of TBA-positive products in embryos of loach Misgurnus fossilis L. at different stages of development under the influence of amino acid derivatives of 1,4-naphthoquinone." Visnyk of Lviv University. Biological series, no. 92 (November 18, 2024): 33–38. http://dx.doi.org/10.30970/vlubs.2024.92.02.

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Naphthoquinones play an important role among natural substances and their synthetic derivatives, as they have a wide range of biological activity. Amino acid derivatives of 1,4-naphthoquinone have prospects for practical use in medicine and pharmacology. To clarify the possible mechanism of action of amino acid derivatives of 1,4-naphthoquinone, the content of TBA-positive products in embryonic cells of the loach Misgurnus fossilis L. during embryogenesis was investigated. Embryos of the freshwater fish loach Misgurnus fossilis L. are a convenient and adequate system for elucidating the mechan

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Danilenko, Nadezhda V., Mariia O. Lutsuk, and Andrei I. Khlebnikov. "4-(Benzoxazol-2-yl)phenyl 3-((3-Chloro-1,4-Naphthoquinon-2-yl)amino)phenyl Sulfate." Molbank 2024, no. 4 (2024): M1930. https://doi.org/10.3390/m1930.

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New 4-(benzoxazol-2-yl)phenyl 3-((3-chloro-1,4-naphthoquinon-2-yl)amino)phenyl sulfate was synthesized via the SuFEx click reaction between fluorosulfate-containing 1,4-naphthoquinone and 2-(4-hydroxyphenyl)benzoxazole. 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) was used as an organic base, while triethylamine was inactive in this reaction.

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Schlauer, Jan, and Andreas Fleischmann. "Naphthoquinones in Pygmy Sundews (Drosera sect. Bryastrum)." Carnivorous Plant Newsletter 50, no. 3 (2021): 111–17. http://dx.doi.org/10.55360/cpn503.js430.

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A detailed study of 44 accessions representing 38 taxa (76% of the diversity known at present) of pygmy sundews (Drosera sect. Bryastrum) reveals the first naphthoquinone patterns in this lineage, in which previous studies have not yielded reliable evidence for naphthoquinones. While most samples do not display detectable amounts of naphthoquinones as previously reported for the group, ramentaceone is detected in three mutually related taxa, and both ramentaceone and its regio-isomer plumbagin is present in all accessions investigated of D. pulchella.

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Genovese, Salvatore, Vito Alessandro Taddeo, Francesco Epifano, and Serena Fiorito. "Complexes of Lapachol and Lawsone with Lanthanides." Natural Product Communications 10, no. 11 (2015): 1934578X1501001. http://dx.doi.org/10.1177/1934578x1501001105.

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Naturally occurring 2-hydroxy-1,4-naphthoquinones are well known to form readily stable complexes with transition metals. In this short communication we describe for the first time the synthesis and preliminary data about structural characterization of complexes between two naturally widespread 2-hydroxy-1,4-naphthoquinones, namely lapachol (1) and lawsone (2), with selected lanthanides like lanthanum, gadolinium, and ytterbium. When tested as cytotoxic compounds, such complexes exhibited an activity that was either higher or equal to that of the parent naphthoquinone.

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Medina, Luis F. C., Valter Stefani, and Adriano Brandelli. "Use of 1,4-naphthoquinones for control of Erwinia carotovora." Canadian Journal of Microbiology 50, no. 11 (2004): 951–56. http://dx.doi.org/10.1139/w04-088.

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The antimicrobial effect of 5 naphthoquinones was tested against the phytopathogenic bacteria Erwinia carotovora. Disk diffusion tests and determination of minimal inhibitory concentrations (MIC) indicate that the compound naphthazarin (NTZ) has the best antibacterial activity among the naphthoquinones tested. Studies on the mode of action indicate the effect of NTZ was bactericidal at 10 µg/mL. When cultivation was done in the presence of sodium ascorbate, the restoration of E. carotovora growth was observed with 3 µg/mL NTZ, but not when a 10 µg/mL dose was used. The incubation of NTZ with b

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Aseeva, Natalia V., Nadezhda V. Danilenko, Evgenii V. Plotnikov, et al. "Synthesis of New 1,4-Naphthoquinone Fluorosulfate Derivatives and the Study of Their Biological and Electrochemical Properties." International Journal of Molecular Sciences 25, no. 22 (2024): 12245. http://dx.doi.org/10.3390/ijms252212245.

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This study presents the synthesis of new fluorosulfate derivatives of 1,4-naphthoquinone by the SuFEx reaction. Anticancer properties of obtained compounds were studied on PC-3 (prostate adenocarcinoma), SKOV-3 (ovarian cancer), MCF-7 (breast cancer), and Jurkat cell lines. All the studied compounds showed higher cytotoxic effects than Cisplatin. The DFT method was applied to determine the electronic structure characteristics of 1,4-naphthoquinone derivatives associated with cytotoxicity. A method of determination of 2,3-dichloro-1,4-naphthoquinone (NQ), 3-chloro-2-((4-hydroxyphenylamino)-1,4-

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34

Migulin, Vasily A. "A New Synthetic Pathway to Symmetric Bisubstituted Naphthoquinones." Synthesis 52, no. 01 (2019): 60–68. http://dx.doi.org/10.1055/s-0039-1690725.

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straightforward and practical synthesis of 2,3-diiodo-1,4-naphthoquinone is reported. Based on the prepared diiodide, a new synthetic approach to symmetric bisubstituted 1,4-naphthoquinones via double Suzuki–Miyaura reaction at room temperature has been researched and developed. The presented general method combines broad-spectrum applicability, efficiency, and simplicity providing target materials in good to quantitative yields.

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35

Polonik, Sergey G., Natalia V. Krylova, Galina G. Kompanets, Olga V. Iunikhina, and Yuri E. Sabutski. "Synthesis and Screening of Anti-HSV-1 Activity of Thioglucoside Derivatives of Natural Polyhydroxy-1,4-Naphthoquinones." Natural Product Communications 14, no. 6 (2019): 1934578X1986067. http://dx.doi.org/10.1177/1934578x19860672.

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Four 1,4-naphthoquinone dithioglucoside derivatives based on natural polyhydroxy-1,4-naphthoquinones were synthesized. These thioglucosides were screened for their antiradical and antiviral activity in vitro. Antiradical activity of tested compounds was determined by the 2,2-diphenyl-1-picrylhydrazyl radical scavenging assay. The anti-herpes simplex virus type 1 (anti-HSV-1) activity of thioglucosides was analyzed by the cytopathic effect inhibition assay and mode of antiviral action was determined by the addition of the tested compounds to uninfected cells, to the virus prior to infection, or

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36

Butler, Mark S., Peter L. Katavic, Paul I. Forster, and Gordon P. Guymer. "Two New Naphthoquinones from the Roots of Conospermum sphacelatum." Australian Journal of Chemistry 52, no. 8 (1999): 813. http://dx.doi.org/10.1071/ch99041.

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Two new naphthoquinones, 8-[(2′E)-3′,7′-dimethylocta-2′,6′-dienyl]-2,7-dihydroxynaphthalene-1,4-dione (1) and 2-hydroxy-6,7-dimethoxy-3-methylnaphthalene-1,4-dione (2), and one known naphthoquinone, (+)-teretifolione-B (3), were isolated from the roots of Conospermum sphacelatum Hook. (Proteaceae) collected in central Queensland. The structures of compounds (1) and (2) were determined by spectroscopic analysis.

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37

Landino, Lisa M., and Joseph A. Reed. "Photochemical Redox Cycling of Naphthoquinones Mediated by Methylene Blue and Pheophorbide A." Molecules 30, no. 6 (2025): 1351. https://doi.org/10.3390/molecules30061351.

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The photoreduction of plastoquinone, a para-benzoquinone, by chlorophyll initiates photosynthesis in chloroplasts. The direct photoreduction of biologically relevant quinones by dietary chlorophyll metabolites has been reported and may influence health outcomes. We examined red light-mediated photoreduction of ortho- and para-naphthoquinones including vitamin K3 using the photosensitizers methylene blue and pheophorbide A, a chlorophyll metabolite. Naphthoquinone reduction was monitored by UV/Visible spectroscopy and required a photosensitizer, red light and a tertiary amine electron donor. Co

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38

Sabutski, Yuri E., Ekaterina S. Menchinskaya, Ludmila S. Shevchenko, et al. "Synthesis and Evaluation of Antimicrobial and Cytotoxic Activity of Oxathiine-Fused Quinone-Thioglucoside Conjugates of Substituted 1,4-Naphthoquinones." Molecules 25, no. 16 (2020): 3577. http://dx.doi.org/10.3390/molecules25163577.

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A series of new tetracyclic oxathiine-fused quinone-thioglycoside conjugates based on biologically active 1,4-naphthoquinones and 1-mercapto derivatives of per-O-acetyl d-glucose, d-galactose, d-xylose, and l-arabinose have been synthesized, characterized, and evaluated for their cytotoxic and antimicrobial activities. Six tetracyclic conjugates bearing a hydroxyl group in naphthoquinone core showed high cytotoxic activity with EC50 values in the range of 0.3 to 0.9 μM for various types of cancer and normal cells and no hemolytic activity up to 25 μM. The antimicrobial activity of conjugates w

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Valderrama, Jaime A., Andrea Pérez-Herrera, Giulio G. Muccioli, et al. "On the Reaction of 2-Alkanoylnaphthohydroquinones with Hydroxylamine: Access to Cytotoxic 2-(Hydroxyamino)-1,4-naphthoquinone and Their 3-(Hydroxyimino)alkyl Analogous." Journal of Chemistry 2022 (August 23, 2022): 1–8. http://dx.doi.org/10.1155/2022/7664037.

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Oximes are known for their anti-inflammatory, antimicrobial, antioxidant, and anticancer activities. Frequently, modification of biologically active carbonyl compounds into oximes leads to increased activity. The present study reports the reactivity of 2-alkanoylnaphthohydroquinones against hydroxylamine under aerial conditions. Results show that, depending on the structure of the hydroquinones, the reaction proceeds through two different chemical pathways to produce 2-(hydroxyamino)-1,4-naphthoquinone and their C-3 (hydroxyimino)alkyl derivatives. Both the formation of the quinoid compounds u

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40

Cameron, Donald W., and Andrew G. Riches. "Reaction of 2-Acetoxy-3-chloro and 2,3-Diacetoxy Naphthoquinones with 1,3-Dioxy and 1,1,3-Trioxy Butadienes." Australian Journal of Chemistry 52, no. 12 (1999): 1165. http://dx.doi.org/10.1071/ch99179.

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Reaction of 2-acetoxy-3-chloro naphthoquinones towards the 1,3-dioxy diene (2) and the 1,1,3-trioxy diene (9) was examined. The competing influence of the acetoxy and chloro substituents was assessed from the regiochemistry of the resulting Diels–Alder chemistry, as was competition between that process and Michael addition/elimination. Reaction of the same dienes towards the less reactive 2,3-diacetoxy naphthoquinone (25) was also investigated.

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Topçu, Seray, and Mine Gül Şeker. "In Vitro Antimicrobial Effects and Inactivation Mechanisms of 5,8-Dihydroxy-1,4-Napthoquinone." Antibiotics 11, no. 11 (2022): 1537. http://dx.doi.org/10.3390/antibiotics11111537.

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Naphthoquinones are an important class of natural organic compounds that have antimicrobial effects. However, the mechanisms of their action remain to be elucidated. Therefore, the antimicrobial activity of the chemically synthesized naphthoquinone derivative, 5,8-dihydroxy-1,4-naphthoquinone, was investigated in this study against 10 different microorganisms. Its inhibitory activity was evident against Bacillus cereus, Proteus vulgaris, Salmonella enteritidis, Staphylococcus epidermidis, S. aureus, and Candida albicans, and its MIC50 values were determined to be 14, 10, 6, 2, 4, 1.2, and <

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Kažemekaite, Maryte, Vilma Railaite, Arunas Bulovas та ін. "Synthesis, Self-Assembling and Redox Properties of 2-[(ω-Sulfanylalkyl)amino]-1,4-naphthoquinones". Collection of Czechoslovak Chemical Communications 71, № 9 (2006): 1383–91. http://dx.doi.org/10.1135/cccc20061383.

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The newly synthesized 1,4-naphthoquinones linked via nitrogen atom to a short chain with terminal sulfanyl group form self-assembled monolayers on gold. The main electrochemical parameters of the monolayers were determined by cyclic voltammetry. Combined voltammetric and in situ Fourier-transform surface-enhanced Raman spectroscopic studies of the Au electrode modified with the title compounds clearly evidence that naphthoquinone group transforms into naphthalenediol during a reduction process.

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43

Jeziorek, Małgorzata, Katarzyna Sykłowska-Baranek, and Agnieszka Pietrosiuk. "Hairy Root Cultures for the Production of Anti-cancer Naphthoquinone Compounds." Current Medicinal Chemistry 25, no. 36 (2018): 4718–39. http://dx.doi.org/10.2174/0929867324666170821161844.

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Background: Recent years have brought the dynamic development in studies of naphthoquinones obtained from plants, in vitro cultures and semi- or total synthesis. This review presents the hairy root cultures approach for producing naphthoquinones and summarizes their most recent anti-cancer investigations. <p> Objective: This review aimed to define biotechnological strategies impacted on naphthoquinones production in hairy root cultures. Up to now the major source of shikonin/alkannin derivatives, rhinacanthins and ramentaceone is isolation from plant material, also derived via biotechnol

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Ribeiro, Marcos, Humberto Stumpf, and Carlos Pinheiro. "Investigating valence tautomerism presence in compounds of Co and naphthoquinone." Acta Crystallographica Section A Foundations and Advances 70, a1 (2014): C1257. http://dx.doi.org/10.1107/s2053273314087427.

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The search for new functional materials involves the development of bistable molecules exhibiting different electronic states with distinct properties at the ambient condition (temperature, pressure, illumination) of application. Coordination compounds, which present electron transfer between metal ion and an organic ligand associated with a change in electron multiplicity of the metal ion, are named valence tautomers(VT)[1]. The chemical equilibrium between two distinct electronic states in VT can be induced by temperature and pressure change as well as by soft X-ray and light irradiation. Th

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Owen, Josee, and K. A. Stewart. "The Effects of Nitrogen on the Growth, Development, and Medicinal Compound Yield of the Sundew Drosera adelae." HortScience 32, no. 3 (1997): 523E—523. http://dx.doi.org/10.21273/hortsci.32.3.523e.

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Drosera spp. are used in alternative medicine as sources of the beneficial naphthoquinone compounds plumbagin (5-hydroxy-2-methyl-1,4-naphthoquinone) and 7-methyljuglone. Presently, Drosera are harvested from the wild with great detriment to bog habitats. This study focused on the development of a hydroponic rockwool culture of the sundew D. adelae. Tissue-cultured plantlets were raised as transplants in peatmoss. The transplants were planted directly into rockwool slabs primed to pH 6. Three levels of ammonium nitrate fertilizer were applied, the highest level of which approximated natural pe

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46

Ourhzif, El-Mahdi, Caroline Decombat, Isabelle Abrunhosa-Thomas, et al. "Synthesis and Biological Evaluation of New Naphthoquinones Derivatives." Current Organic Synthesis 17, no. 3 (2020): 224–29. http://dx.doi.org/10.2174/1570179417666200212111956.

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: New substituted 1,4-naphthoquinones have been prepared in good overall yields through the naphthol route. The cytotoxicity of these compounds was tested in vitro on MCF-7 breast tumor cells. The most active compound 14 displayed an IC50 of 15μM. Objective: To investigate the cytotoxicity of new naphthoquinones derivatives on MCF-7 cells. Methods: Synthesis of new naphtoquinones derivatives and in vitro evaluation of their cytotoxicity on MCF-7 cells (rezasurin cell-based assay). Results: Starting from Ethyl 4-hydroxy-6,7-dimethoxy-2-naphthoate, four naphthoquinones were prepared and exhibite

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47

Hammam, A. S., and B. E. Bayoumy. "Reaction of thioamides with 2,3-dichloro-1,4-naphthoquinone. A novel synthesis of naphtho[2,3-d]thiazole-4,9-diones." Collection of Czechoslovak Chemical Communications 50, no. 1 (1985): 71–79. http://dx.doi.org/10.1135/cccc19850071.

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The reaction of thioamide II with 2,3-dichloro-1,4-naphthoquinone (I) in ethanol gave naptho[2,3-d]thiazole-4,9-diones (IV). The intermediates, 2-thioamido-3-chloro-1,4-naphthoquinones III were also isolated from the reaction medium and could be separately transformed to IV by further boiling in aqueous ethanol containing bicarbonate. The reaction of thiosemicarbazide with I under similar conditions gave naphtho[2,3-e]-2-amino-4H-1,3,4-thiadiazine-5,10-dione (VII).

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Ravichandiran, Palanisamy, Sunirmal Sheet, Dhanraj Premnath, Ae Rhan Kim, and Dong Jin Yoo. "1,4-Naphthoquinone Analogues: Potent Antibacterial Agents and Mode of Action Evaluation." Molecules 24, no. 7 (2019): 1437. http://dx.doi.org/10.3390/molecules24071437.

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1,4-Naphthoquinones have antibacterial activity and are a promising new class of compound that can be used to treat bacterial infections. The goal was to improve effective antibacterial agents; therefore, we synthesized a new class of naphthoquinone hybrids, which contain phenylamino-phenylthio moieties as significant counterparts. Compound 4 was modified as a substituted aryl amide moiety, which enhanced the antibacterial activity of earlier compounds 3 and 4. In this study, five bacterial strains Staphylococcus aureus (S. aureus), Listeria monocytogenes (L. monocytogenes), Escherichia coli (

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Yaseen, Madyan A., and Michael Oelgemöller. "Photochemical Acylation of 1,4-Naphthoquinone with Aldehydes Under Continuous-Flow Conditions." Organics 6, no. 1 (2025): 9. https://doi.org/10.3390/org6010009.

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A series of photoacylations of 1,4-naphthoquinone with various aldehydes and using Pyrex-filtered UVB light was conducted under continuous-flow conditions. Acetone served as a triplet photosensitizer and convenient solvent that kept all materials in solution and could be easily removed. The corresponding acylated 1,4-naphthohydroquinone photoproducts were obtained in acceptable to excellent yields of 30–90% with residence times of just 70 min. The photoacylation process was successfully coupled with in-line oxidation to obtain acylated 1,4-naphthoquinones.

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Khan, Muhammad, Muhammad Ajmal Shah, Mustafa Kamal, Mohammad Shamsul Ola, Mehboob Ali, and Pharkphoom Panichayupakaranant. "Comparative Antihyperglycemic and Antihyperlipidemic Effects of Lawsone Methyl Ether and Lawsone in Nicotinamide-Streptozotocin-Induced Diabetic Rats." Metabolites 13, no. 7 (2023): 863. http://dx.doi.org/10.3390/metabo13070863.

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Our previous study uncovered potent inhibitory effects of two naphthoquinones from Impatiens balsamina, namely lawsone methyl ether (2-methoxy-1,4-naphthoquinone, LME) and lawsone (2-hydroxy-1,4-naphthoquinone), against α-glucosidase. This gave us the insight to compare the hypoglycemic and hypolipidemic effects of LME and lawsone in high-fat/high-fructose-diet- and nicotinamide-streptozotocin-induced diabetic rats for 28 days. LME and lawsone at the doses of 15, 30, and 45 mg/kg, respectively, produced a substantial and dose-dependent reduction in the levels of fasting blood glucose (FBG), Hb

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