• Journal of the Korean Chemical Society
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• v.31 no.5
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• pp.464-470
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• 1987

7-Substituted 2-aminophenazine-5,10-dioxides were synthesized by the reaction of 4-aminophenol with 6-substituted benzofuroxan derivatives which had been obtained from aniline derivatives bearing methoxy, methyl, acetyl, and nitro group at the para position. 2-Aminophenazine-5,10-dioxide was also prepared by the reaction of 4-aminophenol with benzofuroxan. The antimicrobial activities of these phenazine dioxide derivatives were investigated in terms of minimum inhibitory concentration by the common twofold dilution technique. It was observed that the antimicrobial activity of the phenazine dioxides bearing electron releasing substituents was stronger than that of those bearing electron withdrawing substituents. From this result, it was concluded that the antimicrobial activity of phenazine dioxide derivative has a direct relationship with the electronic effect of the substituents.

• YAKHAK HOEJI
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• v.34 no.2
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• pp.112-116
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• 1990

8-Acyl-2-hydroxyphenzaine -5, 10-dioxides and 8-acyl-2-aminophenazine-5, 10-dioxides bearing n-butanoyl, n-hexanoyl and n-octanoyl groups were synthesized. It was attempted to observe the effect of phenazine dioxide derivatives on the hepatic xanthine oxidase activity in this study. As the activity of xanthine oxidase, the key enzyme in the generation of superoxide anion radical ($O_2$), was measured in the presence of phenazine dioxide derivatives, the action of 8-acyl-2-hydroxyphenazine-5,10-dioxide derivatives inhibited with increase of numbers of carbon atom bearing 8-acyl group. Moreover, when plotted on double reciprocal form, the Vmax value decrease as increase of numbers of carbon atom bearing acyl groups without affecting the Km value. However, the hepatic xanthine oxidase activity was not changed by 8-acyl-2-aminophenazine-5,10-dioxide derivatives.

• Journal of the Korean Chemical Society
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• v.33 no.5
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• pp.551-557
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• 1989

7-Alkyl-1,3-dihydroxyphenazine-5,10-dioxides were synthesized by the reaction of 1,3,5-trihydroxybenzene with 6-alkylbenzofuroxans which had been obtained from aniline and n-alkyl alcohols bearing butyl, hexyl and octyl group. 1,3-Dihydroxyphenazine-5,10-dioxide was also prepared by the reaction of 1,3,5-trihydroxybenzene with benzofuroxan. The surface tension of aqueous solutions of these phenazine dioxide derivatives was determined by surface tensiometer and it was found out that the surface tension decreased with an increase of the number of carbon in the alkyl group. The antimicrobial activities of these phenazine dioxide derivatives were investigated in terms of minimum inhibitory concentration by the common twofold dilution technique. The derivative bearing butyl group showed the highest activity among these derivatives examined. It was observed that the antimicrobial activity of these alkyl substituted phenazine dioxide derivatives was stronger than that of the unsubstituted phenazine dioxide derivative.

• Journal of the Korean Chemical Society
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• v.34 no.2
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• pp.189-196
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• 1990

8-Acyl-2-hydroxyphenazine-5,10-dioxides and 8-acyl-2-aminophenazine-5,10-dioxides were synthesized by the reaction of hydroquinone and 4-aminophenol with 6-acylbenzofuroxans which had been obtained from acetanilide and n-acyl chlorides bearing butanoyl, hexanoyl and octanoyl groups. The antimicrobial activities of these phenazine dioxide derivatives were investigated in terms of minimum inhibitory concentration by the common twofold dilution technique. It was observed that the antimicrobial activity of the phenazine dioxide derivatives bearing octanoyl group was stronger than that of those bearing butanoyl and hexanoyl groups in gram positive microorgamisms, but it was observed that the antimicrobial activity and the number of the carbon atom of acyl groups did not have any relation in gram negative microorganisms. When the activity of xanthine oxidase which is the key enzyme in the generation of superoxide anion radical ($O_2^-$), was measured in the presence of phenazine dioxide derivatives, the inhibitory action of the enzyme activity of 8-acyl-2-hydroxyphenazine-5,10-dioxides was increased in accordance with the number of the carbon atom of acyl groups.

• YAKHAK HOEJI
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• v.36 no.5
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• pp.440-448
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• 1992

7-Substituted 2,3-dihydroxyphenazine 5,10-dioxides were synthesized by the reaction of 1,2,4-trihydroxybenzene with 6-substituted benzofuroxan derivatives which had been obtained from aniline derivativies bearing methoxy, methyl, acetyl and nitro group at the para position. 2,3-Dihydroxyphenazine 5,10-dioxide was also prepared by the reaction of 1,2,4-trihydroxybenzene with benzofuroxan. The antimicrobial activities of these phenazine dioxide were investigated in terms of minimum inhibitory concentration by the common twofold dilution technique. It was observed that the antimicrobial activity of the phenazine dioxides bearing electron releasing substituents was stronger than that of those bearing electron withdrawing substitutents. From this result, it was concluded that the antimicrobial activity of phenazine dioxide derivatives has a direct relationship with the electronic effect of the substituents.

• Journal of the Korean Chemical Society
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• v.30 no.1
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• pp.126-134
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• 1986

7-Alkyl-2-aminophenazine-5,10-dioxides bearing butyl, hexyl and octyl group were synthesized by the reaction of 4-aminophenol with 6-alkylbenzofuroxans which had been obtained from aniline and n-alkyl alcohols. And 2-aminophenazine-5,10-dioxide was prepared by the reaction of 4-aminophenol with benzofuroxan. Infrared, nuclear magnetic resonance spectrophotometers, and elemental analyzer were employed to identify the products concerned with the synthetic processes. Surface tension of aqueous solutions of these phenazine derivatives was determined by surface tensiometer and it was found that the surface tension decreased with an increase of the number of carbon in the alkyl group. Antimicrobial activities were evaluated in terms of minimum inhibitory concentration by a dilution method. The butyl derivative showed the highest activity among these derivatives. It was observed that the antimicrobial activity of these alkyl substituted 2-aminophenazine-5,10-dioxides was stronger than that of 2-aminophenazine-5,10-dioxide.

• Journal of the Korean Chemical Society
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• v.27 no.6
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• pp.457-463
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• 1983

-Alkyl-2-hydroxyphenazine-5,10-dioxides were synthesized from hydroquinone, and alkyl benzofuroxanes which were previously obtained through five reaction steps starting from aniline. Infrared, nuclear mangnetic resonance spectrometry and elemental analysis were employed to identify the products concerned in the synthetic processes. It was observed that these alkylated phenazine oxides lowered the surface tension of water substantially. These derivatives showed stronger antimicrobial activity against both gram positive and negative microbes than 1-carboxyphenazine which had no alkyl side chain. It was also found that the antimicrobial activity of the phenazine compound increased when the nitrogen of the ring was bound to the oxygen atom.