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1

Utkina, Natalia K., and Natalia D. Pokhilo. "Free Radical Scavenging Activities of Naturally Occurring and Synthetic Analogues of Sea Urchin Naphthazarin Pigments." Natural Product Communications 7, no. 7 (2012): 1934578X1200700. http://dx.doi.org/10.1177/1934578x1200700725.

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Antioxidant activities of minor pigments of sea urchins (1–5) and synthetic naphthazarins (7–13) were evaluated and compared with echinochrome A (6) using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) (ABTS) scavenging assays. Structure-activity relationships showed that the antioxidant activities of the tested compounds depended on the number and positions of hydroxyl groups. Compounds bearing 3 or 2 hydroxyl groups on a naphthazarin core (5,8-dihydroxy-1,4-naphthoquinone) were the most active in both assays. Echinochrome A (6) (IC50 7.0 μM) and it
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2

Polonik, Nikita S., Yuri E. Sabutskii, and Sergey G. Polonik. "Free Radical Scavenging Activity of Synthetic and Naturally Occurring Polyhydroxy-, Aminohydroxynaphthazarins and Related Compounds." Natural Product Communications 13, no. 10 (2018): 1934578X1801301. http://dx.doi.org/10.1177/1934578x1801301021.

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Fifty natural and synthetic hydroxy-, aminohydroxynaphthazarins and related quinones were tested for their antiradical activities using 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) (ABTS) scavenging assay. The main features of structure-antiradical activity relationship of amino- and hydroxyquinones were determined for the first time. It was found that naphthazarins (5,8-dihydroxy-1,4-naphthoquinones) are much more active against ABTS-radical than related 1,4-naphthoquinones and 5-hydroxy-1,4-naphthoquinones. Natural aminonaphthazarins (spinamine E, echinamine A) and polyhydroxylated naph
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3

Pokhilo, N. D., V. A. Denisenko, and V. F. Anufriev. "Chemistry of naphthazarin derivatives. Transetherification selectivity of naphthazarin methoxy derivatives." Russian Journal of Organic Chemistry 50, no. 5 (2014): 647–53. http://dx.doi.org/10.1134/s1070428014050054.

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4

Pokhilo, N. D., A. Ya Yakubovskaya, and V. P. Glazunov. "Chemistry of naphthazarin derivatives: XV. Bromination of naphthazarin and its derivatives." Russian Journal of Organic Chemistry 47, no. 4 (2011): 504–9. http://dx.doi.org/10.1134/s1070428011040063.

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5

Swager, Timothy, Cagatay Dengiz, and You-Chi Wu. "Synthesis and Optoelectronic Properties of Iptycene–Naphthazarin Dyes." Synlett 30, no. 01 (2018): 54–58. http://dx.doi.org/10.1055/s-0037-1611169.

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We report the synthesis and characterization of iptycene–naphthazarin dyes by using a sequential Diels–Alder approach. The tautomerization of naphthazarin was used as the key step in the synthesis, with structures confirmed by single-crystal X-ray and NMR analysis. The systematic trends in electronic properties were investigated by UV/Vis spectroscopy. BF2 complexes of the dyes were prepared by reaction with BF3·OEt2 in CH2Cl2.
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6

Kikuchi, Masashi, Kazuo Komatsu, and Motokiyo Nakano. "The alkylamination of naphthazarin." Dyes and Pigments 12, no. 2 (1990): 107–18. http://dx.doi.org/10.1016/0143-7208(90)80003-8.

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7

Anufriev, V. Ph, S. G. Polonik, N. D. Pokhilo, and N. N. Balanyova. "Chemistry of naphthazarin derivatives. 11. Trisubstituted hydroquinone derivatives in the preparative synthesis of naphthazarins." Russian Chemical Bulletin 52, no. 10 (2003): 2247–50. http://dx.doi.org/10.1023/b:rucb.0000011886.03785.bd.

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8

Utkina, Natalia K., and Natalia D. Pokhilo. "Antioxidant Activity of 1’-Hydroxyethylnaphthazarins and their Derivatives." Natural Product Communications 12, no. 12 (2017): 1934578X1701201. http://dx.doi.org/10.1177/1934578x1701201218.

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The ABTS•+ radical cation scavenging activity of known (2-5, 9, 10) and new (6-8) 1’-hydroxyethylnaphthazarins and their products of esterification and etherification was evaluated and a structure-activity relationship was studied. It was shown, that the structure of side chains does not affect the radical scavenging activity of 1’-hydroxyethylnaphthazarins and their derivatives. The presence of methoxyl groups on the naphthazarin core slightly enhanced the antioxidant activity of compounds compared with compounds without methoxyl groups. The presence of the additional hydroxyl group on the na
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9

Carmen Carreño, M., J. Luis García Ruano, and Antonio Urbano. "Tautomeric equilibrium of naphthazarin thioderivatives." Tetrahedron 50, no. 17 (1994): 5013–20. http://dx.doi.org/10.1016/s0040-4020(01)90412-0.

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10

Chizhova, A. Ya, T. Yu Kochergina, V. F. Anufriev, V. A. Denisenko, and V. P. Glazunov. "The chemistry of naphthazarin derivatives." Russian Chemical Bulletin 48, no. 5 (1999): 938–43. http://dx.doi.org/10.1007/bf02494641.

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11

Malinovskaya, G. V., A. Ya Chizhova, and V. F. Anufriev. "The chemistry of naphthazarin derivatives." Russian Chemical Bulletin 48, no. 5 (1999): 1010–11. http://dx.doi.org/10.1007/bf02494659.

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12

Tchizhova, A. Ya, V. Ph Anufriev, V. P. Glazunov, and V. A. Denisenko. "The chemistry of naphthazarin derivatives." Russian Chemical Bulletin 49, no. 3 (2000): 466–71. http://dx.doi.org/10.1007/bf02494776.

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13

Utkina, Natalia K., Natalia D. Pokhilo, and Lyubov N. Atopkina. "Antiradical Activity of Naphthazarin-Carbohydrate Nonglycoside Conjugates." Natural Product Communications 14, no. 5 (2019): 1934578X1984817. http://dx.doi.org/10.1177/1934578x19848170.

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The ABTS·+ scavenging activity of known (4, 6-8) and new (5, 9-12) naphthazarin-carbohydrate nonglycoside conjugates, and methoxynaphthazarins 1-3 was evaluated. The study of structure-activity relationships showed that the presence of carbohydrate fragments in the structure of naphthazarin-carbohydrate conjugates increased their antiradical activity compared with starting methoxynaphthazarins. Antiradical activity depends on the structure of carbohydrate fragments, their number, and position. Depending on the carbohydrate fragment the activity increased in the following order: methyl-α-d-gluc
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14

Lozano, Héctor J., Natalia Busto, Gustavo Espino, et al. "Interstrand DNA covalent binding of two dinuclear Ru(ii) complexes. Influence of the extra ring of the bridging ligand on the DNA interaction and cytotoxic activity." Dalton Transactions 46, no. 11 (2017): 3611–22. http://dx.doi.org/10.1039/c6dt04888a.

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15

Dengiz, Cagatay, Sarah P. Luppino, Gregory D. Gutierrez, and Timothy M. Swager. "Naphthazarin-Polycyclic Conjugated Hydrocarbons and Iptycenes." Journal of Organic Chemistry 82, no. 14 (2017): 7470–80. http://dx.doi.org/10.1021/acs.joc.7b01170.

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16

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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17

Peng, Ying, Wen Zhou, Min Zhang, et al. "A convenient and efficient synthesis of naphthazarin." Journal of Chemical Research 35, no. 1 (2011): 24–25. http://dx.doi.org/10.3184/174751911x12964930076669.

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18

Phelps, D. C. "Immunoassay for Naphthazarin Phytotoxins Produced byFusarium solani." Phytopathology 80, no. 3 (1990): 298. http://dx.doi.org/10.1094/phyto-80-298.

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19

Kundaković, Tatjana, Tatjana Stanojković, Zorica Juranić, and Nada Kovačević. "Cytotoxicityin vitro of naphthazarin derivatives fromOnosma arenaria." Phytotherapy Research 20, no. 7 (2006): 602–4. http://dx.doi.org/10.1002/ptr.1899.

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20

CARRENO, M. C., J. L. GARCIA RUANO, and A. URBANO. "ChemInform Abstract: Tautomeric Equilibrium of Naphthazarin Thioderivatives." ChemInform 25, no. 39 (2010): no. http://dx.doi.org/10.1002/chin.199439143.

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21

Aljanadi, Omar, Kousi Alzoubi, Rosi Bissinger, and Florian Lang. "Stimulation of Suicidal Erythrocyte Death by Naphthazarin." Basic & Clinical Pharmacology & Toxicology 117, no. 6 (2015): 369–74. http://dx.doi.org/10.1111/bcpt.12420.

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22

Tanoue, Yasuhiro, Akira Terada, Hiroshige Taniguchi, et al. "A Novel Synthesis of Naphthazarin and Juglone Derivatives by Reaction of Naphthazarin and Juglone with Cyclic Enol Ethers." Bulletin of the Chemical Society of Japan 66, no. 12 (1993): 3712–15. http://dx.doi.org/10.1246/bcsj.66.3712.

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23

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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24

Chaisuksant, R. "Spectrophotometric determination of copper in alloys using naphthazarin." Talanta 53, no. 3 (2000): 579–85. http://dx.doi.org/10.1016/s0039-9140(00)00534-8.

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25

Arnone, Alberto, Lucio Merlini, Gianluca Nasini, and Orso Vajna de Pava. "Direct Amination of Naphthazarin, Juglone, and Some Derivatives." Synthetic Communications 37, no. 15 (2007): 2569–77. http://dx.doi.org/10.1080/00397910701462864.

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26

Afshar Ghahremani, Fatemeh, Mansoureh Zahedi-Tabrizi, and Sayyed Faramarz Tayyari. "The nature of intramolecular hydrogen bond in Naphthazarin." Chemical Physics 538 (October 2020): 110907. http://dx.doi.org/10.1016/j.chemphys.2020.110907.

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27

Yamamoto, Yoshikazu, Hideki Matsubara, Yasuhiro Kinoshita, et al. "Naphthazarin derivatives from cultures of the lichen Cladonia cristatella." Phytochemistry 43, no. 6 (1996): 1239–42. http://dx.doi.org/10.1016/s0031-9422(96)00495-5.

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28

Peng, Ying, Wen Zhou, Min Zhang, et al. "ChemInform Abstract: A Convenient and Efficient Synthesis of Naphthazarin." ChemInform 42, no. 19 (2011): no. http://dx.doi.org/10.1002/chin.201119092.

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29

Paul, S. O., C. J. H. Schutte, and P. J. Hendra. "The Fourier Transform Raman and infrared spectra of naphthazarin." Spectrochimica Acta Part A: Molecular Spectroscopy 46, no. 2 (1990): 323–29. http://dx.doi.org/10.1016/0584-8539(90)80101-4.

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30

Schutte, C. J. H., S. O. Paul, and D. Röhm. "The symmetry group of labile intramolecularly hydrogen-bonded naphthazarin." Journal of Molecular Structure: THEOCHEM 232 (July 1991): 179–88. http://dx.doi.org/10.1016/0166-1280(91)85253-4.

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31

Papageorgiou, Vassilios P., Andreana N. Assimopoulou, Elias A. Couladouros, David Hepworth, and K. C. Nicolaou. "Chemie und Biologie von Alkannin, Shikonin und verwandten Naphthazarin-Naturstoffen." Angewandte Chemie 111, no. 3 (1999): 280–311. http://dx.doi.org/10.1002/(sici)1521-3757(19990201)111:3<280::aid-ange280>3.0.co;2-y.

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32

Chaisuksant, Rasamee, Lertnapa Pattanarat, and Kate Grudpan. "Naphthazarin modified carbon paste electrode for determination of copper(II)." Microchimica Acta 162, no. 1-2 (2007): 181–88. http://dx.doi.org/10.1007/s00604-007-0879-8.

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33

You, Young-Jae, Xiang-Guo Zheng, Kim Yong, and Byung-Zun Ahn. "Naphthazarin derivatives: Synthesis, cytotoxic mechanism and evaluation of antitumor activity." Archives of Pharmacal Research 21, no. 5 (1998): 595–98. http://dx.doi.org/10.1007/bf02975381.

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34

Kułacz, Karol, Michał Pocheć, Aneta Jezierska, and Jarosław J. Panek. "Naphthazarin Derivatives in the Light of Intra- and Intermolecular Forces." Molecules 26, no. 18 (2021): 5642. http://dx.doi.org/10.3390/molecules26185642.

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Our long-term investigations have been devoted the characterization of intramolecular hydrogen bonds in cyclic compounds. Our previous work covers naphthazarin, the parent compound of two systems discussed in the current work: 2,3-dimethylnaphthazarin (1) and 2,3-dimethoxy-6-methylnaphthazarin (2). Intramolecular hydrogen bonds and substituent effects in these compounds were analyzed on the basis of Density Functional Theory (DFT), Møller–Plesset second-order perturbation theory (MP2), Coupled Clusters with Singles and Doubles (CCSD) and Car-Parrinello Molecular Dynamics (CPMD). The simulation
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35

Burns, CJ, M. Gill, AH Binothman, BW Skelton, and AH White. "Pigments of Fungi. XXIII. Approaches Towards (±)-Austrocortirubin From 3-Methyl-1-trimethylsilyloxybuta-1,3-diene." Australian Journal of Chemistry 44, no. 12 (1991): 1715. http://dx.doi.org/10.1071/ch9911715.

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The products (5) and (21) of cycloaddition between 3-methyl-1-trimethylsilyloxybuta-1,3-diene (3) and naphthazarin (4), and between (3) and the naphthopurpurin acetal (2), respectively, are converted into the tetrahydroanthraquinones (16)-(18), (26) and (27) via a series of intermediate epoxy alcohols. Stereochemical assignments are corroborated by a single-crystal X-ray structure analysis of the bromohydrin (16). The tetrahydroanthraquinones (27) and (18), advanced intermediates in a proposed synthesis of the fungus pigment austrocortirubin (1) and its 6-demethoxy analogue (20), respectively,
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36

Dragan, Sergey V., Michael A. Pushilin, Valery P. Glazunov, Vladimir A. Denisenko, and Victor Ph Anufriev. "Total Synthesis of Hybocarpone, a Cytotoxic Naphthazarin Derivative from the Lichen Lecanora hybocarpa, and Related Compounds." Natural Product Communications 9, no. 12 (2014): 1934578X1400901. http://dx.doi.org/10.1177/1934578x1400901227.

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The concise synthesis of the lichen-derived antitumor agent hybocarpone (1) and its analogs is described. A new synthetic approach is based on the direct oxidative dimerization of the available naphthazarin precursors in the formation of the binaphtho[2,3- b; 2,3- d]furantetraone structure. It was shown that the first step to tetrahydrofuran features is the bridging hindered S*, S* and R*, S* carbon-carbon bonds of the molecules, setting the relative configurations of the 5a S*,6a S*,12a S*,12b S* and 5a S*,6a R*,12a R*,12b S* diastereomers.
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37

Mukherjee, Tulsi, Edward J. Land, A. John Swallow, J. Malcolm Bruce, Paul C. Beaumont, and Barry J. Parsons. "Aspects of the oxidation of naphthazarin as studied by pulse radiolysis." Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases 84, no. 10 (1988): 3423. http://dx.doi.org/10.1039/f19888403423.

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38

Chen, DeZhan, ZhaoLing Hao, Xue Zhao, and Zhen Wang. "Theoretical study on the photochemical properties of naphthazarin and halogen substitution." Journal of Molecular Structure: THEOCHEM 803, no. 1-3 (2007): 73–77. http://dx.doi.org/10.1016/j.theochem.2006.09.030.

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39

Kikuchi, Masashi, and Hajime Matsuda. "NOVEL HUMAN HAIR DYES III Human Hair Dyeing by Leuco-naphthazarin." Sen'i Gakkaishi 45, no. 6 (1989): 272–77. http://dx.doi.org/10.2115/fiber.45.6_272.

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40

Masuda, Kazuaki, Shinji Funayama, Kanki Komiyama, Iwao Umezawa, and Katsumi Ito. "Constituents of Tritonia crocosmaeflora, II. Tricrozarin B, an Antitumor Naphthazarin Derivative." Journal of Natural Products 50, no. 5 (1987): 958–60. http://dx.doi.org/10.1021/np50053a036.

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41

Razieh, Farahati, and Zahedi-Tabrizi Mansoureh. "Calculation of intramolecular hydrogen bonding strength of naphthazarin with chlorine substitution." Clinical Biochemistry 44, no. 13 (2011): S311—S312. http://dx.doi.org/10.1016/j.clinbiochem.2011.08.996.

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42

Jacquemin, Denis, Cyril Peltier, and Ilaria Ciofini. "Visible spectrum of naphthazarin investigated through Time-Dependent Density Functional Theory." Chemical Physics Letters 493, no. 1-3 (2010): 67–71. http://dx.doi.org/10.1016/j.cplett.2010.04.071.

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43

TANOUE, Y., A. TERADA, H. TANIGUCHI, et al. "ChemInform Abstract: Synthesis of Naphthoquinone Derivatives. Part 13. A Novel Synthesis of Naphthazarin and Juglone Derivatives by Reaction of Naphthazarin and Juglone with Cyclic Enol Ethers." ChemInform 25, no. 13 (2010): no. http://dx.doi.org/10.1002/chin.199413152.

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44

Sung-Hoon, Kim, Lee Eun mi, and Bae Jin-Seok. "Naphthazarin: Colorimetric Detection of Cr3+ Using Highly Selective F- Chemosensor." Sen'i Gakkaishi 71, no. 6 (2015): 213–16. http://dx.doi.org/10.2115/fiber.71.213.

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45

Burns, CJ, M. Gill, and S. Saubern. "Pigments of Fungi. XXI. Synthesis of (±)-6-Demethoxyaustrocortirubin." Australian Journal of Chemistry 44, no. 10 (1991): 1427. http://dx.doi.org/10.1071/ch9911427.

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6-Demethoxyaustrocortirubin (6) is synthesized via the epoxide (21) which is available in 73% yield over four steps from naphthazarin (10). Hydrolysis of the epoxide (21) yields the diol (25) which on hydrogenolysis affords 6-demethoxy-1-deoxyaustrocortirubin (7). Stereoselective benzylic hydroxylation of (7) gives (6). Cleavage of the epoxide (21) with sodium acetate in acetic acid affords a mixture of the esters (22)-(24), while methanolysis yields the isomeric ethers (29) and (30). Hydrogenolysis of (22), (23) and (29) gives high yields of (7). Potentially more direct routes to the alcohol
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46

TANOUE, Yasuhiro, Akira TERADA, Kazunori SAKATA, et al. "Convenient Synthesis of Ethylidenedinaphthazarins by Reaction of Naphthazarin with Ethyl Vinyl Ether." NIPPON KAGAKU KAISHI, no. 12 (1996): 1029–32. http://dx.doi.org/10.1246/nikkashi.1996.1029.

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47

Idriss, Kamal A., and Magda M. S. Saleh. "Acid–base characteristics of naphthazarin and solution equilibria of yttrium(III) chelates." Analyst 118, no. 2 (1993): 223–27. http://dx.doi.org/10.1039/an9931800223.

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48

Papageorgiou, Vassilios P., Andreana N. Assimopoulou, Elias A. Couladouros, David Hepworth, and K. C. Nicolaou. "The Chemistry and Biology of Alkannin, Shikonin, and Related Naphthazarin Natural Products." Angewandte Chemie International Edition 38, no. 3 (1999): 270–301. http://dx.doi.org/10.1002/(sici)1521-3773(19990201)38:3<270::aid-anie270>3.0.co;2-0.

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49

Masuda, Kazuaki, Shinji Funayama, Kanki Komiyama, Iwao Unezawa, and Katsumi Ito. "Constituents of Tritonia crocosmaeflora, I. Tricrozarin A, a Novel Antimicrobial Naphthazarin Derivative." Journal of Natural Products 50, no. 3 (1987): 418–21. http://dx.doi.org/10.1021/np50051a012.

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50

Yao, Masaru, Shinji Umetani, Hisanori Ando, et al. "Rechargeable organic batteries using chloro-substituted naphthazarin derivatives as positive electrode materials." Journal of Materials Science 52, no. 20 (2017): 12401–8. http://dx.doi.org/10.1007/s10853-017-1368-z.

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