• Archives of Pharmacal Research
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• v.28 no.7
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• pp.750-755
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• 2005

A series of 2-arylamino-5-hydroxy-naphthalene-1,4-diones, 3-arylamino-5-methoxy-naphthalene-1,4-diones, and 2-arylamino-3chloro-5-hydroxy-naphthalene-1,4-diones were synthesized and tested for in vitro antifungal activity against the species Candida and Aspergillus niger. Among those tested, 3-arylamino-5-methoxy-naphthalene-1,4-diones exhibited potent antifungal activity. In general, the 3-arylamino-5-methoxy-naphthalene-1,4-diones showed more potent antifungal activity than the 2-arylamino-5-hydroxy-naphthalene-1,4-diones and the 2-arylamino-3-chloro-5-hydroxy-naphthalene-1,4-diones.

• Bulletin of the Korean Chemical Society
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• v.32 no.7
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• pp.2428-2432
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• 2011

A series of new 4-aryl-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-diones have been synthesized via three component reaction of 1,3-dimethylbarbituric acid with arylglyoxals in the presence of hydrazinium dihydrochloride in ethanol. All of these derivatives may act as potential monoamine oxidase inhibitors.

• Archives of Pharmacal Research
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• v.21 no.5
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• pp.599-609
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• 1998

In search for new antitumor agents, twelve 6-aziridinylbenzimidazole derivatives were synthesized and their cytotoxicities were tested against three cancer cell lines (mouse lymphocytic leukemia P388 and B16, and human gastric carcinoma SNU-16). From 4-amino-3-nitrotoluene as the starting material, 2-(acetoxymethyl)benzimidazoles (5a-d) were obtained by Phillips reaction. These benzimidazoles were then reacted with Fremy's salt to give a mixture of three 2-(acetoxymethyl) (8a-c) and four 2-(hydroxymethyl)benzimidazole-4,7-diones (9a-d). Addition of these quinones with aziridine afforded 6-aziridinyl-2-(acetoxymethyl) (10a-c) and 6-aziridinyl-2-(hydroxymethyl)benzimidazole-4,7-diones (11a-d). Utilizing 2-(hydroxymethyl)benzimidazole-4,7-diones (9b,d), esters 10d and 13e-h were prepared by the sequential reactions of esterification and addition. The synthesized compounds show potent cytotoxicity against all of three cell lines tested. The cytotoxicities of 10a-d or 11a-d against SNU-16 were wuperior to those of 13e-h, and were equal to or slightly higher than that of mitomycin C. compounds 11a-d were slightly more cytotoxic than 10a-d in all cell lines tested.

• Archives of Pharmacal Research
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• v.29 no.4
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• pp.276-281
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• 2006

A series of 8-alkyl-and 8-aryl-8,9-dihydro-7H-isoindolo[5,6-g]quinoxaline-7,9-diones were synthesized using sultine chemistry as a key step in good yield. These compounds were evaluated for their in vitro cytotoxicity against six human cancer cell lines (HCT15, SK-OV-3, A549, SNB19, MCF7 and MCF7/ADR).

• Journal of the Korean Chemical Society
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• v.47 no.2
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• pp.137-146
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• 2003

3-Hydroxybenzopyran[3,2-c]-[1]-benzopyran-6,7-diones (3) and 3-methoxycarbonylcoumarin (4) were prepared via condensation of 1 with resorcinol in the presence of sodium methoxide. The chemical behavior of 3 towards acetic anhydride, alkyl halides and diazonium chloride is described. The electron impact ionization mass spectra of compounds 4,5 and 6a,b show a weak molecular ion peak and a base peak of m/z 89, m/z 280. m/z 91 and m/z 120 resulting from a cleavage fragmentation respectively. The molecular ion of compounds 3, 6b, and 7a is a base peak of m/z 280, m/z 366 and m/z 488 respectively. Compound 7a give a characteristic fragmentation pattern with a two very stable fragmentation of m/z 383 and m/z 77.

• 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.

• Bulletin of the Korean Chemical Society
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• v.32 no.7
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• pp.2171-2177
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• 2011

Synthetic route has been developed for the synthesis of new (Z)-5-[4-(2-chloroquinolin-3-yl) methoxy]benzyl-idinethiazolidine-2,4-diones (6a-h) starting from 2-chloro-3-hydroxymethyl quinolines (2a-h). The hydroxy methyl quinolines on tosylation yielded (3a-h). Condensation of the tosyl intermediates with 4-hydroxy benzaldehydes has been carried in DMF in presence of $K_2CO_3$ and obtained 4-quinolinyl methoxy benzaldehydes (4a-h). Conveniently Knoevenagel condensation of quinolinyl methoxy benzaldehydes (4a-h) and 2, 4-thiazolidinedione (5) has been carried in PEG-400 in presence of L-proline and obtained better yields of the titled compounds (6a-h).

• Bulletin of the Korean Chemical Society
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• v.27 no.4
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• pp.484-488
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• 2006

The solid-phase synthesis of new series of 1,6,8-trisubstituted tetrahydro-2H-pyrazino[1,2-a]pyrimidine-4,7-diones as bicyclic $\beta$-turn mimetics is described. Their NF-kB inhibition activities were tested and the effect of substituents on bicyclic ring was investigated. Among the prepared compounds, the fluorobenzyl and methoxybenzyl group substituted compounds 26 and 27 at C-1 and C-8 position showed more inhibitory activities than the others. Tested at a concentration of 10 uM, these two compounds showed a 60% inhibition against the target NF kB 549.

• Bulletin of the Korean Chemical Society
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• v.27 no.7
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• pp.1063-1066
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• 2006

• Journal of the Korean Chemical Society
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• v.40 no.7
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• pp.519-525
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• 1996

3-Carbomethoxy-1(3H)-isobenzofuranone(9) underwent condensation with ${\alpha}{\beta}-unsaturated$, esters 3a-b to produce the corresponding naphthacene-6,7-diones 11a-b with high yields in one pot procedure. Among the naphthacene-6,7-diones formed, compound 11a without an ethyl group at C-9 position was oxidized to give the naphthacene-5,12-dione 13a, while compound 11b containing the ethyl group was oxidized to give a 3:2 mixture of the naphthacene-5,7,12-trione 12b and naphthacene-5,12-dione 13b under the same experimental conditions.