• YAKHAK HOEJI
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• v.32 no.4
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• pp.245-250
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• 1988

Naphthoquinone derivatives have been found to be anticoagulant. In this report, several new 2-chloro-3-(N-arylamino)-naphthoquinone derivatives were synthesized in oder to develope mild anticoagulant. 2, 3-dichloro-1, 4-naphthoquinone was reacted with p-aminobenzoic acid, m-aminobenzoic acid, toluidine, m-nitroaniline, sulfanilamide, sulfathiazole, sulfaguanidine, phenetidine, 2-aminopyrimidine and 3-amino-5-methylisoxazole in EtOH or AcOH afford 2-chloro-3-(p-carboxy anilino)-naphthoquinone (1), 2-chloro-3-(m-carboxyanilino)-naphthoquinone (2),2-chloro-3-(toluidino)-naphthoquinone (3),2-chloro-3-(m-nitroanilino)-naphthoquinone (4), 2-chloro-3-(4-sulfanilanilino)-naphthoquinone (5), 2-chloro-3-(4-sulfathiazolino)-naphthoquinone (6),2-chloro-3-(4-sulfaguanidino)-naphthoquinone (7),2-chlro-3-(phenetidino)-naphthoquinone (8), 2-chloro-3-(pyrimidine-2-amino)-naphthoquinone (9) and 2-chloro-3-(5-methylisoxazole-3-amino)-naphthoquinone (10) in good yield.

• Journal of Korean Society of Forest Science
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• v.97 no.3
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• pp.199-203
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• 2008

By comparison of mass fragmentation pattern of each component with two modern MS libraries (NIST and Wiely 6), those were identified to one aliphatic alcohol (3-ethyl-2-methyl-1-pentene-3-ol) and three naphthoquinone derivatives (1,4-naphthoquinone, 5-hydroxy-1,4-naphthoquinone (juglone) and 5-hydroxy-2-methyl-1,4-naphthoquinone (plumbagin)). According to the quantitative study with authentic compounds of three naphthoquinone derivatives, 1,4-naphthoquinone and 5-hydroxy-1,4-naphthoquinone were the major volatile components in the root shell of Juglans mandshurica and their amounts were ca. $54.4{\mu}g/g$ and $21.3{\mu}g/g$, respectively.

• YAKHAK HOEJI
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• v.34 no.1
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• pp.15-21
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• 1990

-4,9-dione derivatives were prepared from $2-chloro-3-({\alpha}-accetyl-{\alpha}-ethoxycarbonyl-methyl)-1,4-naphthoquinone$ and 2-chloro-3-N-phenylamino-1,4-naphthoquinone. $2-Chloro-3-({\alpha}-acetyl-{\alpha}-ethoxycarbonyl-methyl)-1,4-naphthoquinone$ was reacted with amines to give $2-amino-3-({\alpha}-acetyl-{\alpha}-ethoxycarbonyl-methyl)-1,4-naphthoquinone$ derivatives. Subsequent treatment of $2-amino-3-({\alpha}-acetyl-{\alpha}-ethoxycarbonyl-methyl)-1,4-naphthoquinone$ with sodium ethoxide gave -4,9-dione derivatives. When 2-chloro-3-N-phenylamino-1,4-naphthoquinone reacted with sodium ${\alpha}-cyano$ ethyl acetate, 2-amino-3-ethoxycarbonyl-N-phenyl--4,9-dione was obtained. However, with sodium diethyl malonate, not -4,9-dione but 2-chloro-3-bis-(methoxycarbonyl)-methyl-2H-3-N-phenylamino-1,4-naphthoquinone was obtained.

• Food Science and Biotechnology
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• v.18 no.3
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• pp.755-760
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• 2009

The growth-inhibiting activities of persimmon roots-derived materials against intestinal bacteria were evaluated and compared with that of 1,4-naphthoquinone as a positive control. The active constituent isolated from persimmon roots was characterized as 5-hydroxy-2-methyl-1,4-naphthoquinone using various spectroscopic analyses. Treatment with 1,4-naphthoquinone at a dose of 1.0 mg/disc strongly inhibited the growth of 6 intestinal bacteria. Furthermore, when the structure-activity relationships of 1,4-naphthoquinone's derivatives were evaluated, 5-hydroxy-2-methyl-1,4-naphthoquinone and 2-methyl-1,4-naphthoquinone were found to strongly inhibit the growth of Clostridium difficile, Clostridium perfringens, and Escherichia coli without adversely affecting the growth of Bifidobacterium adolescentis, Bifidobacterium longum, and Lactobacillus acidophilus. Additionally, 2-hydroxy-1,4-naphthoquinone and 5-hydroxy-1,4-naphthoquinone strongly inhibited the growth of C. difficile and C. perfringens, but did not inhibit the growth of E. coli. Taken together, these results indicate that persimmon roots-derived materials and some of 1,4-naphthoquinone's derivatives could be useful preventive agents against diseases caused by harmful intestinal bacteria.

• Journal of Photoscience
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• v.11 no.32
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• pp.61-63
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• 2004

Some quinones such as 1,4-benzoquinone 2, 1,4-naphthoquinone 3 and 1,2-naphthoquinone 4 dissolved in diethylamine were irradiated with 300 nm UV light to afford red aminoquinones 6, 7, and 9 as the major products. Irradiation of a solution of a primary product, i.e., 2,5-bis(diethylamino)-1,4-benzoquinone 6 in benzene gave 2,5-bis (ethylamino)-1,4-benzoquinone 10 in 80% yield, along with an oxazoline 11 in 19% yield via photochemical deethylation. A solution of 2-diethylamino-1,4-naphthoquinone 7 in benzene was also irradiated under the same condition, in which 2-ethylamino-1,4-naphthoquinone 12 was obtained in ca. 100% yield.

• Applied Chemistry for Engineering
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• v.2 no.4
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• pp.348-355
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• 1991

Polysiloxane copolymers were prepared by copolymerizing hexamethylcyclotrisiloxane with tetramethylcyclotetrasiloxane, and then reacted with allyamine. Copolymers containing naphthoquinone-1,2-diazide-5-sulfonyl group were synthesized by reacting naphthoquinone-1,2-diazide-5-sulfonyl chloride with siloxane copolymers having amino group. Thermal decomposition temperatures of copolymers were $360{\sim}450^{\circ}C$, and photosensitive characteristics were dependent on the molecular weights of backbone resins and sensitizers. Sensitivity of copolymers was $50{\sim}120mJ/cm^2$ and contrast(${\gamma}$) was 1.4~2.1.

• Journal of Life Science
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• v.27 no.3
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• pp.325-333
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• 2017

High level of plasma cholesterol is strongly associated with the development of atherosclerosis and coronary heart disease. Clinical trials designed to reduce plasma cholesterol level by diet or pharmacological intervention have resulted in marked reduction of disease incidence. The enzyme 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase which reduces cholesterol biosynthesis in the liver is the key enzyme of the mevalonate pathway that produces cholesterol. In this study, 71 naturally occurring phenolic compounds were tested for inhibitory activities against HMG-CoA reductase. Eleven compounds out of 71 showed inhibitory activities: three hydrolyzable tannin (geraniin, acetonyl geraniin and pentagalloyl ${\beta}-D-glucose$), four benzoic acid derivatives (benzoic acid, trans-cinnamic acid, 2,4-dihydroxybenzoic acid and 2,5-dihydroxybenzoic acid), and four naphthoquinone derivatives (1,2-naphthoquinone, 1,4-naphthoquinone, plumbagin and shikonin). At the concentration of $10{\mu}g/ml$, 1,4-naphthoquinone inhibited HMG-CoA reductase by 99.4%, and then plumbagin 91.4%, pentagalloyl ${\beta}-D-glucose$ 46.6%, 2,4-dihydroxybenzoic acid 40.9%, shikonin 37.7%, 1,2-naphthoquinone 36.6%, trans-cinnamic acid 32.0%, acetonyl geraniin 30.2%, benzoic acid 28.5%, geraniin 28.3% and 2,5-dihydroxybenzoic acid 22.3%, respectively. $IC_{50}$ values of 1,4-naphthoquinone and plumbagin was $2.1{\mu}g/ml$ and $5.8{\mu}g/ml$, respectively.

• Applied Chemistry for Engineering
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• v.10 no.8
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• pp.1169-1174
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• 1999

2-Diazo-1-naphthoquinone-5-sulfonyl chloride(NQD-Cl) was synthesized from sodium 2-diazo-naphthoquinone-5-sulfonate by chlorination. NQD-Cl was esterified with hydroxybenzophenones to give several 1,2-naphthoquinone-(2)-diazide-5-sulfonic acid ester derivatives(NQD-esters). We have compared benzophenone derivatives with methoxy group to benzophenone derivatives with hydroxy group. Solubility of each NQD-ester was studied. Each of NQD-esters was formulated with novolac base resin and PS plates were manufactured. Photosensitivity, bleachability, compatible exposed time and relative sensitivity were determined by UV spectrophotometry, imaged by UV lithographic techniques, and the gray scale method. According to the number of substituted NQD group, it showed that relative sensitivity was different from gray scale method. NQD-esters with methoxy group showed a good solubility and higher sensitivity than commercial PS ones.

• Korean Journal of Pharmacognosy
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• v.23 no.4
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• pp.240-247
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• 1992

Impatiens balsamina Linne(Balsaminaceae) known as 'BONG SUN HWA' in Korea and has been used for the treatment of scrofulosis, carbunculus and dysenteria etc. Bioassay-guided fractionation of MeOH extract from the whole plants of Impatiens balsamina has afforded a simple naphthoquinone derivative, 2-methoxy-1,4-naphthoquinone. The structure of this compound was established by spectroscopic methods. This compound possessed strong antifungal activity against Candida albicans, AspergiIlus niger, Crytococcus neoformans and Epidermophyton floccusum. The activity of 2-methoxy-1,4-naphthoquinone on E. floccusum $(MIC{\;}:{\;}5.0{\;}{\mu}g/ml)$ was the same potency as that of nystatin. It showed also strong antibacterial activity against gram-positive bacteria Bacillus subtilis as well as gram-negative bacteria Salmonella typhimurium. Although the activity of this compound on gram-negative bacteria was lower than that of gram-positive bacteria.

• YAKHAK HOEJI
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• v.34 no.6
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• pp.422-428
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• 1990

2,3-Dibromo-1,4-naphthoquinone was reacted with p-aminobenzoic acid, 2-aminopyridine, 2-amino-4-metylpyridine, m-nitroaniline, sulfathiazol, p-chloroaniline, phenetidine and 2-bromo-3-(N-arylamino)-1,4-naphthoquinones($1{\sim}8$). 2,3-Epoxy-2,3-dihydro-1,4-naphthoquinone was also reacted with p-amonobenzoic acid, p-toluidine, p-chloroaniline, m-chloroaniline, m-nitroaniline, p-phenetidine, N,N-dimethyl-1,4-pheylenediamine as a ring opening and dehydogenation to form 2-hydroxy-3-(N-arylamino)-naphthoquinones ($9{\sim}16$) in good yield. These new compounds($1{\sim}16$) are expected to have a biological activities such as anticoagulant and cytotoxic.