• YAKHAK HOEJI
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• v.41 no.5
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• pp.582-587
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• 1997

The 6.7-dichloroquinoline-5,8-dione (I) was reacted with ethyl acetoacetate in the presence of sodium ethoxide to yield 6-(${\alpha}$-acetyl-${\alpha}$-ethoxycarbonyl methyl)-7-chloro-qui noline-5,8-dione(II). When this compound II was reacted with some arylamine (phenyl, p-toluyl, p-fluorophenyl, p-chlorophenyl. p-bromophenyl, p-iodophenyl, p-trifluoromethylphenyl, p-dimethylaminophenyl,indanyl), 1N-aryl-2-methyl-3-ethoxycarbonyl pyridino[2,3-f]-indole-4.9-dione(IIIa-I) were obtained via intramolecular cyclization.

• YAKHAK HOEJI
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• v.40 no.1
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• pp.19-24
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• 1996

The 6,7-dichloroquinolone-5,8-dione(I) was reacted with ethyl acetoacetate in the presence of sodium ethoxide to yield 6-(${\alpha}$-acetyl-${\alpha$-ethoxycarbonyl-methyl)-7-chloro-quin oline-5,8-dione(II). When this compound II was reacted with some alkylamine (methylamine, ethylamine, propylamine, isopropylamine, cyclopropylamine, methoxyethylamine, ethanolamine, benzylamine, furfurylamine), 1N-alkyl-2-methyl-3-ethoxycarbonyl-pyridino(2,3f)-indole-4,9-dione(IIIa-i) were obtained via intramolecular cyclization.

• Journal of the Korean Chemical Society
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• v.18 no.6
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• pp.437-442
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• 1974

Pentacyclo ($5,3,0,0^{2,5},06{3,9},0^{4,8})-decane-6,10-dione was synthesized from the cyclopentanone in good overall yield(60%). Cyclopentanone ethylene ketal(Ⅰ) was brominated with pyridinium bromide perbromide, and the brominated ketal(Ⅱ) was converted to the dimer of cyclopentadienone ethylene ketal(Ⅲ). The ethylene ketal(Ⅲ) was again converted to the dicyclopentadiene-1,8-dione(Ⅳ). Finally, the pentacyclo ($5,3,0,0^{2,5},06{3,9},0^{4,8})-decane-6,10-dione(Ⅴ) was synthesized from the dicyclopentadilene-1,8-dione(Ⅳ) by photochemical cyclization.

• Natural Product Sciences
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• v.17 no.1
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• pp.5-9
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• 2011

An alkaloid, 3-methylcanthin-5, 6-dione, was isolated from the stem of Picrasma quassioides (D. Don) Benn. and characterized by comprehensive analyses of its 1D and 2D NMR spectra. It was also evaluated for its cytotoxic activity in vitro against three human cancer cell lines (MDA-MB-231, HT-29 and NCI-N87), using MTT assays. We found that 3-methylcanthin-5, 6-dione exhibited significant anti-inflammatory activity via inhibiting NO production induced in LPS-stimulated murine macrophage RAW264.7 cells. The antioxidant activity of 3-methylcanthin-5, 6-dione was measured by DPPH free radical scavenging assays, hydroxyl radical scavenging assays and reducing power assays. Our results showed that 3-methylcanthin-5, 6-dione has significant biological activities.

• Bulletin of the Korean Chemical Society
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• v.25 no.12
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• pp.1769-1774
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• 2004

Jun/Fos, a crucial factor in transmitting the tumor-promoting signal from the extracellular environment to the nuclear transcription machinery, has a dimerization interface possessing several coiled structural properties. Jun and Fos can interact with the DNA regulatory region, AP-1 (Activator Protein-1), which is composed of 5'-TGAC/GTCA-3'.$^1$ Curcumin is a well-known anticancer and anti-inflammatory compound.$^{2,3}$ It also acts as an inhibitor of the Jun-Fos function. c-Fos and c-Jun with a bZIP region are overexpressed in BL21 E. coli and purified with an $Ni^{2+}$ affinity column. The inhibitors of Fos-Jun-AP-1 complex formation were searched through the EMSA (electrophoresis mobility shift assay) experiment, and new curcuminoids were synthesized and investigated as to their inhibitory effect on the same system. Two curcuminoids showed a stronger inhibitory effect than curcumin. This inhibitory activity was quantified with EMSA. 1,7-bis(4-methyl)-1,6-heptadiene-3,5-dione (BJC003) and 1,7-bis(4-hydroxy-5-methoxy-3-nitrophenyl)-1,6-heptadiene-3,5-dione (BJC005) showed remarkably high inhibitory activities. $IC_{50}$ of 1,7-bis(4-methyl)-1,6-heptadiene-3,5-dione (BJC003) and 1,7-bis(4-hydroxy-5-methoxy-3-nitrophenyl)-1,6-heptadiene-3,5-dione (BJC005) are 8.98 ${\mu}M$ and 5.40 ${\mu}M$, respectively. However, 1,7-bis(4-methyl-3-nitrophenyl)-1,6-heptadiene-3,5-dione (BJC004) did not show inhibitory activity.

• YAKHAK HOEJI
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• v.41 no.5
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• pp.575-581
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• 1997

The 6,7-dichlorquinoline-5,8-dione was reacted with ${alpha}$-cyanoacetic acid ethyl ester in ammonia solution to yield 6-(${alpha}$-cyano-${alpha}$-ethoxycarbonyhnethyl)-7-chloroquinoline- 5,8-dione (compound I). When this compound was reacted with some alkyl amines (methylamine, ethylamine, isopropylamine, etc) 2-amino-3-ethoxycarbonyl-N-alkyl-pyridino[2,3-f]indole-4,9-diones (compounds II a-e) were obtained.

• YAKHAK HOEJI
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• v.40 no.4
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• pp.382-386
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• 1996

The compound of the 6,7-dichloroquinoline-5,8-dione has two asymmetric chloro radicals at the position of the C6 and C7. When the compound reacts with ethyl acetoacetate in the presence of sodium ethoxide, it is considered that C6 and/or C7 position of the compound can be substitued. The exact substitued position of the product (I) could not be identified by the NMR analysis in our experiment. Therefore, we synthesized the 3-ethoxycarbonyl-2-methyl-1-N-propyl pyridino(2,3f)indole-4,9-dione by reaction of the product (I) with propylamine via intramolecular cyclization to identify the substitued position of the product (I) using the X-ray crystallographic structure analysis. The result demonstrates that the position of nucleophilic substitution of the product (I) is at the position of the C6.

• Archives of Pharmacal Research
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• v.15 no.2
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• pp.138-141
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• 1992

The new N-aryl-benz[f]-indole-4, 9-dione derivatives were synthesized via in tramolecular cyclization when triethylamine was employed as a base for the reaction of 2-chloro-3-$(\alpha$-cyano-$\alpha$-ethoxycarbonyl-methyl)-1, 4-naphthoquinone and arylamines.

• Journal of Life Science
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• v.14 no.2
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• pp.351-355
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• 2004

Saccharin derivatives were synthesized by means of 4 reaction steps involved the reaction of 1-methylurea (or 1-methylthiourea) and oxalyl chloride. 1-Alkyl(or phenyl)-3-(1,1,3-trioxo-1,3-dihydro-1$^{6}$ -benzo[d]isothiazol-2-ylmethyl)-imidazolidine-2,4,5-trione 5 and 1-alkyl(or phenyl)-2-thioxo- 3-(1,1,3-trioxo-1,3-dihydro-1$^{6}$ -benzo-[d]isothiazol-2-ylmethyl)-imidazolidine-4,5-dione 12 were obtained by means of 4 reaction steps involved the reaction of 1-methyl-urea(or 1-methylthiourea) and oxalyl chloride.

• Proceedings of the PSK Conference
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• 2002.10a
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• pp.342.1-342.1
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• 2002

6.7-Dicholroquinoline-5.8-dione reacted with 2-aminopyridine derivatives, Out of the four possible products which could be achieved in this reaction. condensation and rearrangement product. 4a.10.11-triazabenzo［3.2-a］ fluorine-5.6-dione was obtained as major product. The definite structure was identified with X-ray crystallographic study. (omitted)