• Bulletin of the Korean Chemical Society
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• v.20 no.6
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• pp.663-666
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• 1999

The 4-methylene-1,3-dioxolane(4-MDO) derivatives with dimethoxyphenyl group on the 2-position of 1,3-dioxolane ring, 2-(x,y-dimethoxyphenyl)-4-MDO derivatives (x,y=2,3(1b), 2,4(2b), 2,5(3b) and 3,4(4b)) were prepared by acelalizationof the corresponding benzaldehyde with 3-chloro-1,2-propanediol, followed by dehydrochlorination. 2-(Dimethoxy)phenyl-4-MDO derivatives underwent polymerization wiht ring opening as will as cyclization reaction to afford a mixture of the ring-opened polymer and 3(2H)-dihydrofuranone derivative with boron trifluoride as a cationic catalyst. Both the methylene group and 1,3-dioxolane ring were participated in the reaction with cationic catalyst. The key intermediate of the polymerization is a benzyl cation generated by ring opening, and the cyclization reaction proceed via proton addition to oxygen atom of 1,3-dioxolane ring.

• Proceedings of the PSK Conference
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• 2002.10a
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• pp.251.2-251.2
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• 2002

2-Methylaminoethyl- 4,4' -dimethoxy- 5, 5',6,6' -dimethylenedioxybiphenyl- 2' -carboxy- 2-carboxylate (DDB-S) is a synthetic compound derived from DDB. which is protects liver against carbon tetrachloride-, D-galactosamine-, thioacetamine-, and prednisolone- induced hepatic injury in experimental animals. We assessed the use of liquid chromatography/electrospray iontrap tandem mass spectrometry (LC/MS/MS) method to identify and quantify in vivo metabolites and to measure excretion. (omitted)

• Bulletin of the Korean Chemical Society
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• v.20 no.4
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• pp.456-458
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• 1999

The synthesis of 6-amino-3-benzylpyrrolo[2,3-c]acridine (9) and its 8,9-dimethoxy derivative (10) from N-benzyl-4,5,6,7-tetrahydroindol-4-one and anthranilonitriles, via imine formation followed by cyclization and aromatisation, is described.

• Proceedings of the PSK Conference
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• 2000.04a
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• pp.170.1-170.1
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• 2000

• Toxicological Research
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• v.14 no.3
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• pp.307-313
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• 1998

Dimethyl dimethoxy biphenylate (DDB) is an agent used to treat hepatits. DDB-S (DDB-soluble), a new DDB derivative, was synthsized to increase water solubility of the original DDB. In the present study, the antigenic potential of DDB-S was examined by active systemic anaphylaxis (ASA), passive cutaneous anaphylaxis (PCA) and passive hemagglutination (PHA) tests. The experimental groups consist of a low dosage group, a high dosage group, he group emulsified with Freund's complete adjuvant (FCA, ASA test) or an alum (PCA and PHA tests) and the macromolecule conjugate group emulsified with FCA or an alum. In the ASA test, all experimental groups showed negative responses whereas the positive control group given ovalbumin plus FCA showed severe anaphylactic responses. In the heterologous PCA test using mice and rats, positive responses were not detected in any of the experimental groups. In the PHA test, all experimental groups showed negative responses whereas the positive control group given ovalbumin plus an alum showed 512~2048 PHA titers. These results demonstrated that DDB-S does not have any antigenic potential. These can be utilized as a part of preclinical data for the development of DDB-S as an intravenous injection.

• BMB Reports
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• v.38 no.3
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• pp.300-306
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• 2005

Tamoxifen citrate is an anti-estrogenic drug used for the treatment of breast cancer. It showed a degree of hepatic carcinogenesis, when it used for long term as it can decrease the hexose monophosphate shunt and thereby increasing the incidence of oxidative stress in liver rat cells leading to liver injury. In this study, a model of liver injury in female rats was done by intraperitoneal injection of tamoxifen in a dose of 45 mg/kg body weight for 7 successive days. This model produced a state of oxidative stress accompanied with liver injury as noticed by significant declines in the antioxidant enzymes (glutathione-S-transferase, glutathione peroxidase and catalase) and reduced glutathione concomitant with significant elevations in TBARS (thiobarbituric acid reactive substance) and liver transaminases; sGPT (serum glutamate pyruvate transaminase) and sGOT (serum glutamate oxaloacetate transaminase) levels. The oral administration of dimethyl dimethoxy biphenyl dicarboxylate (DDB) in a dose of 200 mg/kg body weight daily for 10 successive days, resulted in alleviation of the oxidative stress status of tamoxifen-intoxicated liver injury in rats as observed by significant increments in the antioxidant enzymes (glutathione-S-transferase, glutathione peroxidase and catalase) and reduced glutathione concomitant with significant decrements in TBARS and liver transaminases; sGPT and sGOT levels. The administration of DDB before tamoxifen intoxication (as protection) is more little effective than its curative effect against tamoxifen-induced liver injury. The data obtained from this study speculated that DDB can mediate its biochemical effects through the enhancement of the antioxidant enzyme activities and reduced glutathione level as well as decreasing lipid peroxides.

• Journal of Life Science
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• v.13 no.6
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• pp.836-842
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• 2003

1-(2-Aminophenyl)pyrrole 5 was synthesized by using 1,2-phenylenediamine with 2,5-dimethoxy-tetrahydrofuran in glacial acetic acid. 1-(3-Aminophenyl)pyrrole 7 and 1,3-dipyrrolylbenzene 8 were obtained by using 1,3-phenylene-diamine with 2,5-dimethoxytetrahydrofuran in glacial acetic acid. 1,4-Dipyrrolylbenzene 10 was synthesized by using 1,4-phenylenediamine with 2,5-dimethoxy-tetrahydrofuran in glacial acetic acid. Aminophenylpyrroles 5, 7 and dipyrrolylbenzenes 8, 10 were respectively synthesized by treatment of 1,2-phenylenediamine, 1,3-phenylenediamine, 1,4-phenylene-diamine and 2,5-dimethoxytetrahydrofuran in (1) no solvent or (2) acrylic acid or (3) silica gel or (4) acrylic acid and silica gel or (5) silica gel and glacial acetic acid instead of glacial acetic acid. The best yield for dipyrrolylbenzene 10 was obtained when silica gel and glacial acetic acid was used. 9-Phenyl-carbazole 11 was synthesized by treatment of 1-phenylpyrrole with 2,5-dimethoxy-tetrahydrofuran in glacial acetic acid.

• Journal of Pharmaceutical Investigation
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• v.27 no.3
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• pp.173-179
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• 1997

A water-soluble DDB derivative (Bis{2-(methylamino)ethyl}-4,4-dimethoxy-5,5',6,6'-dimethylenedioxy-biphenyl-2,2'-dicarboxylate, DDB-S) was synthesized and its therapeutic effects on the liver damage induced by carbon tetrachloride in rats were evaluated. Oral administration of DDB-S reduced the aspartate aminotransferase(AST) and alanine aminotransferase(ALT) activities and increased total protein and albumin contents in the serum of the carbon tetrachloride intoxicated rat. Therapeutic effects of DDB-S by intravenous injection was also investigated using carbon tetrachloride intoxicated rats. Histological studies showed that IV injection of DDB-S had improved the typical necrosis around centrilobular area in liver tissue due to the carbon tetrachloride intoxication and also prevented the elevation of liver weigh/body weight ratio. IV administration of DDB-S to $CCl_4-treated$ rats significantly decreased AST & ALT activities and also prevented the decrease of aniline hydroxylation activity of the liver. These results indicate that i.v. administration of DDB-S is very effective in recovering the liver function in $CCl_4-treated$ rats.

• YAKHAK HOEJI
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• v.44 no.2
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• pp.141-148
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• 2000

A new synthetic method of 6-(1-oxyalkyl)-5,8-dimethoxy-1,4-naphthoquinones was developed, 2-formyl-1,4,5,8-tetramethoxynaphthalene was oxidized to form 6-formyl-5,8-dimethoxy-1,4-naphthoquinone(DMNQ). This was selectively reduced and benzylated to produce 6-formyl-5,8-dimethoxy-1,4-dibenzyloxynaphthalene, to which various alkylmagnesium halide were added, followed by debenzylation and oxidation in sequence, yielding 6-(1-hydroxyalkyl)-DMNQ derivatives. 6-(1-hydroxyalkyl)-5,8-diethoxy-1,4-naphthalene (DENQ) derivatives were synthesized by similar procedure. 1'-OH of the naphthoquinone derivatives was acylated with various alkanoic acids to give 6-(1-acyloxyalkyl)-DMNQ or DENQ derivatives. TOPO-I inhibitory activity and cytotoxicity of DENQs were less potent than that of DMNQs. Among the DMNQ and DENQ analogues, the ones with alkyl group being heptyl were most potent in TOPO-I inhibition $IC_{50}$/; 30.1, 36.4 $\mu$M). DUNQ derivatives with a longer side chain exhibited a weaker cytotoxicity. A correlation between size of the alkyl side chain and cytotoxicity was not observed for DENQ derivatives. Acylation of 1'-hydroxyl group, in general, decreased both TOPO-I inhibitory activity and cytotoxicity T/C (%) values of the DENQ derivatives on S-180 intraperitoneal tumor were larger than those of DMNQ derivatives. Among the compounds synthesized,6-(1-hydroxyheptyl)-DENQ and 6-(1-hex-anoyloxyoctyl)-DMNQ showed the highest T/C values of 183% and 182%, respectively.

• Food Engineering Progress
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• v.14 no.4
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• pp.292-298
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• 2010

Wheat germ contains the glycosylated forms of 2-methoxy-p-benzoquinone (2-MBQ) and 2,6-dimethoxy-p-benzoquinone (2,6-DMBQ), both of which have antimicrobial and immunostimulatory effects. Conversion of glycosylated 2-MBQ and 2,6-DMBQ to their more functional unglycosylated forms requires enzymatic action of $\beta$-glucosidase. We investigated the applications of lactic acid bacteria and yeast that produce $\beta$-glucosidase as starters for production of unglycosylated 2-MBQ and 2,6-DMBQ from wheat germ. Lactobacillus zeae and Pichia pijperi were selected through $\beta$-glucosidase enzyme assays for 37 yeast strains and five strains of lactic acid bacteria. Lb. zeae was more efficient than P. pijperi at producing 2-MBQ and 2,6-DMBQ from wheat germ. After 48 hr of fermentation with a mixed culture of Lb. zeae and P. pijperi, the concentration of 2-MBQ was 0.46${\pm}$0.07 mg/g, indicating an approximately 1.6-fold higher concentration than that obtained by pure culture of Lb. zeae. However, the concentration of 2,6-DMBQ was not significantly enhanced by fermentation with a mixed culture of Lb. zeae and P. pijperi.