• YAKHAK HOEJI
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• v.43 no.5
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• pp.652-658
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• 1999

To reveal the inhibitory mechanism of NO-dependent vasorelaxation by quinone derivatives (OQ1 and OQ21), we have compared the generation of free radicals by oxidative stress and the formation of cellular adducts by arylation. First, we measured oxygen consumption by quinone derivatives as a marker of oxidative stress in order to investigate whether these quinone compounds could generate reactive oxygen species. Both OQ1 and OQ21 generated free radicals and OQ21 was more potent. These results suggested that free radicals be involved in the inhibition of vasorelaxation by quinones. Next, we measured the binding capacity of quinone derivatives with intracellular GSH and protein thiols (-SH) in order to investigate whether these quinones have arylation capacity. Compared to positive control groups (menadione), both OQ1 and OQ21 depleted intracellular GSH and protein thiols very slightly. These compounds have low toxicities in mammalian tissues. From these results, we concluded that the inhibition of vasorelaxation by quinone derivatives (OQ1, OQ21) may be cuased by generation of free radicals.

• YAKHAK HOEJI
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• v.37 no.1
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• pp.49-53
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• 1993

Arylalkanoic acid derivatives are known as good non-steroidal antiinflamatory and antirheumatic agents. The new arylalkanoic acid derivatives were synthesized when 2-chloro-3-($\alpha$-cyano-$\alpha$-ethoxycarbonyl-methyl)-1, 4-naphthoquinone was reacted with some arylamines.

• Archives of Pharmacal Research
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• v.19 no.6
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• pp.535-542
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• 1996

Seven isoazamitosene derivatives, mitomycin analogues, were synthesized and tested for cytotoxicities against leukemia and gastric cancer cell lines. Preparation of a pyrrolo[1, 2-a]benzimidazole (3) (azamitosene ring system) was completed by utilizing the Lewis acid-catalized cyclization, with .omicron.-chloronitrotoluene as the starting material. Nitration of 3 produced a mixtue of two isomers (5-nitro isomer (4) and 7-nitro isomer (5)) in product ratio of 36 : 52. 4 was directly converted into quinone (7) by reduction and Fremy oxidaton. Finally, quinone derivatives (8, 9, 10, and 11) were synthesized by 1, 4-addition of 7 with cyclic secondary amines. From above-mentioned 5, 8-nitro compound (15) was prepared in 4 steps. At pH 3, Fremy oxidation of 15 produced quinone (16), whereas iminoquinone derivatives (17a and 17b) at pH 7. Isoazamitosene derivatives (8, 9, 10, and 11), containing cyclic amino groups at the 7-position, showed potent cytotoxicity on P388, SNU-1, and KHH tumor cell lines. Among them, 8 had stronger cytotoxicity against SNU-1 cell line than mitomycin and adriamycin. Considering these results, isoazamitosene derivatives may had unique cytotoxicity profiles. However, isoiminoazamitosene derivatives (17a and 17b) revealed very weak cytotoxicity.

• Current Applied Physics
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• v.18 no.12
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• pp.1507-1512
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• 2018

The development of an organic-based aqueous redox flow battery (RFB) using quinone as an electroactive material has attracted great attention recently. This is because this battery is inexpensive, produces high energy density, and is environment friendly in stationary electrical energy storage applications. Herein, we investigate the redox potentials and solubilities of indole-5,6-quinone and indole-4,7-quinone derivatives in terms of the substituent effects of functional groups using theoretical calculations. Our results indicate that full-site substituted derivatives of indolequinone are more useful as active materials compared to single-site substituted derivatives. In particular, our calculations reveal that the substitution of $-PO_3H_2$ and $-SO_3H$ functional groups with multiple polar bonds is very effective in increasing the activity of the aqueous RFB. As a strategy to overcome the limitation that the aqueous solubility is intrinsically low because they are organic molecules, we suggest the substitution of functional groups with multiple polar bonds to the backbones of active organic materials. Among 180 indolequinone derivatives, 17 candidates that meet the redox potential standards ($${\leq_-}0.2V$$ or $${\geq_-}0.9V$$) and eight candidates with solubility exceeding 2 mol/L are identified. Three indolequinone derivatives that satisfy both conditions are finally presented as promising electroactive candidates for an aqueous RFB.

• Proceedings of the PSK Conference
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• 2002.10a
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• pp.351.2-351.2
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• 2002

We have previously reported the synthesis and cytotoxic activities of a series of azaanthraquinone derivatives on the model of doxorubicin(Dox). Dox is known to intercalate into DNA and to inhibit topoisomerase II activity. But in the case of Quinone compounds like Dox. its use is limited because of systemic toxicities. primarily cardiotoxicity and myelosuppression. In this study. we describe the synthesis of benzoquinoxaline derivatives as DACA analogue. DACA has a neutral chromophore and acridine moiety and posions both topoisomerases I and ll with DNA intercalating activity. In order to delineate the SAR of benzoquinoxaline derivatives. an effcient sythetic rout to the target compounds without quinone group. Various attempted removal of quinone from benzoquinoxlinedione was unsuccessful. Diels-Alder rout applied for the synthesis of the target compounds will be discussed.

• Proceedings of the PSK Conference
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• 2003.10b
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• pp.174.1-174.1
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• 2003

We have previously reported the synthesis and cytotoxic activities of a series of azaanthraquinone derivatives using doxorubicin as a lead compound. Doxorubicin is known to intercalate into DNA and to inhibit topoisomerase II activity. But in the case of quinone compounds like Dox, its use is limited because of systemic toxicities, primarily cardiotoxicity and myelosuppression. In this study, we discuss the synthesis of isoindolobenzoquinoxaline derivatives. The quinone group of the azaanthraquinone derivatives were removed in the target compounds. (omitted)

• Environmental Analysis Health and Toxicology
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• v.8 no.3_4
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• pp.13-21
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• 1993

In order to evaluate the anticancer activity of 1,4-naphthoquinone derivatives, several 1,4-naphthoquinone derivatives were newly synthesized and subjected to mouse leukemia p-388 cell line by MTT cytotoxicity assay. Among the several 1,4-naphtho-quinone derivatives, YC-001 has showed the most potent anticancer activity. To determine the safety of YC-001, hematotoxicity was tested. YC-001 induced hemolysis increased with both concentration and time dependent manner. The mechanism of hemolysis considered to be the generation of oxygen free radicals and lipid peroxydation of erythrocyte membrane which composed of phospholipids. Also methemoglobin, oxidized form of hemoglobin, was formed by YC-001.

• Journal of the Korean Applied Science and Technology
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• v.14 no.2
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• pp.27-34
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• 1997

Naphthoquinone-1,2-diazide-5-sulfonyl [NDS]derivatives members of Quinone diazide compound that are utilizable as photoresist for printing plate were synthesized, and photoresist were prepared by mixing these derivatives with a matrix resin(PF, CF) at various weight ratios. Photosensitive characteristics of photoresist were studied by Gray scale method, and SEM to analyze if they can be used as photosensitive material in a printing plate. Experimental results showed using IR, UV, NDS derivatives were photoconverted and developer-soluble photoresist were produced. Photoresist in the mixing ratio of 1:4 of NDS[II] and CF resin gave rise to the highest dissolution rate. In addition, photoresist obtained at this condition resulted in the most superior sensitivity.

• Journal of Food Hygiene and Safety
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• v.11 no.1
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• pp.31-34
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• 1996

Aloe, being used widely as a health food and also as a traditional folk remedy for burns and constipation, contains quinone derivatives particularly in its skin. Thus, we have investigated the effect of extracts of Aloe in ethanol metabolism. The dried powder of water extract of skinned Aloe (300 mg/kg body weight given to rats by oral adminstration at 30 min prior to oral adminstration of ethanol given at a does of 4 gm/kg) and the freeze-dried Aloe gel commercial product (600 mg/kg) which was prepared after selective elimination of quinones were found not to increase the ethanol metabolism rate in vivo. This result suggested that quinones, missing from the above preparations, might be responsible for enhancing ethanol metabolism rate.

• Archives of Pharmacal Research
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• v.29 no.2
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• pp.123-130
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• 2006

1,4-Naphthoquinones are widely distributed in nature and many clinically important antitumor drugs containing a quinone moiety, such as anthracyclines, mitoxantrones and saintopin, show excellent anticancer activity. In this study, 2- or 6-substituted 5,8-dimethoxy-1,4-naphthoquinone (DMNQ) and 5,8-dihydroxy-1,4-naphthoquinone (DHNQ) derivatives were synthesized, and their cytotoxic activity against L1210 and P388 cancer cells was examined. Their antitumor activity was also assessed in mice bearing S-180 cells in the peritoneal cavity. In comparison with the DMNQ derivatives, the DHNQ derivatives exhibited more potent bioactivities than the DMNQ derivatives against both L1210 and P388 cells in vitro and S-180 cells in vivo. The $ED_{50}$ values of the DHNQ derivatives against P388 cells were in the range of 0.18-1.81 ${\mu}g/mL$ whereas those of the DMNQ derivatives were in the range of 0.26-40.41 ${\mu}g/mL$. The T/C ($\%$) values of the DHNQ derivatives, 8, 17, 18, 19, and 20, were found to be comparable to or even better than that of adriamycin. It was also observed that the 2-substituted derivatives (8, 19, 20) showed better antitumor activity than the 6-substituted derivatives (7, 17, 18) in the mice bearing S-180 cells in the peritoneal cavity.