Synthesis and cytotoxicity of 2-methyl-4, 9-dihydro-1-substituted-1H-imidazo[4,5-g]quinoxaline-4,9-diones and 2,3-disubstituted-5,10-pyrazino[2,3-g]quinoxalinediones.

doi:10.1021/JM970695N

Paper

Synthesis and cytotoxicity of 2-methyl-4, 9-dihydro-1-substituted-1H-imidazo[4,5-g]quinoxaline-4,9-diones and 2,3-disubstituted-5,10-pyrazino[2,3-g]quinoxalinediones.

Published Oct 24, 1998 · H. Yoo, M. Suh, Sang Woo Park

Journal of medicinal chemistry

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36

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0

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Abstract

Series of 2-methyl-4,9-dihydro-1H-imidazo[4,5-g]quinoxaline-4, 9-diones and 5,10-pyrazino[2,3-g]quinoxalinediones have been synthesized from 6,7-dichloro-5,8-quinoxalinedione for developing new anticancer drugs. Intercalation complex of 2-methyl-4, 9-dihydro-1-methyl-1H-imidazo[4,5-g]quinoxaline-4,9-dione with GC/GC base pairs by a computer graphics-aided method was parallel to the axis of the helix. The interaction energies of synthetic compounds were low. 2-Methyl-4,9-dihydro-1-(4-bromophenyl)-1H-imidazo[4, 5-g]quinoxaline-4,9-dione, which has the lowest interaction energy of the test compounds, was identified as being more cytotoxic against human gastric adenocarcinoma cells (MKN 45) than adriamycin and cis-platin in vitro using the MTT assay. The IC50 value of this compound was 1.30 microM, whereas those of adriamycin and cis-platin were 3.13 and 86.5 microM, respectively. The cytotoxicity of 2, 3-diethyl-5,10-pyrazino[2,3-g]quinoxalinedione was comparable to that of adriamycin in the in vitro assay. However these compounds showed loss of activity on human lung adenocarcinoma cells (PC 14) and human colon adenocarcinoma cells (colon 205). These results suggest that 2-methyl-4,9-dihydro-1-(4-bromophenyl)-1H-imidazo[4, 5-g]quinoxaline-4,9-dione, with the lowest interaction energy, might be an excellent and selective antitumor agent against MKN 45.

In Vitro Study

Study Snapshot

2-methyl-4,9-dihydro-1-(4-bromophenyl)-1H-imidazo[4, 5-g]quinoxaline-4,9-dione shows potential as an excellent and selective antitumor agent against human gastric adenocarcinoma cells,

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Synthesis and cytotoxicity of 2-methyl-4, 9-dihydro-1-substituted-1H-imidazo[4,5-g]quinoxaline-4,9-diones and 2,3-disubstituted-5,10-pyrazino[2,3-g]quinoxalinediones.

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References

Citations

A Survey of Synthetic Routes and Antitumor Activities for Benzo[g]quinoxaline-5,10-diones

Benzo[g]quinoxaline-5,10-diones show promising antitumor properties and potential for improved anthracycline antibiotics in cancer chemotherapy.

Synthesis and anti‐proliferative activity studies of 2‐(2‐(trifluoromethyl)‐6‐(substituted)imidazo[1,2‐ b ]pyridazin‐3‐yl)‐ N ‐(substituted)acetamide derivatives

Novel imidazo[1,2 b ]pyridazin3yl acetamide derivatives show anti-proliferative activity against A-549 and Du-145 cancer cell lines, with compounds 9e, 9g, and 9h showing activity comparable to doxorubicin.

CYTOTOXIC EFFECTS OF DULOXETINE ON MKN45 AND NIH3T3 CELL LINES AND GENOTOXIC EFFECTS ON HUMAN PERIPHERAL BLOOD LYMPHOCYTES.

Duloxetine has less genotoxicity than cisplatin at concentrations under 200 M, but shows cytotoxic effects and is not a better choice for gastric cancer therapies compared to cisplatin.

CYTOTOXIC EFFECTS OF ARIPIPRAZOLE ON MKN45 AND NIH3T3 CELL LINES AND GENOTOXIC EFFECTS ON HUMAN PERIPHERAL BLOOD LYMPHOCYTES.

Aripiprazole shows potential as a cytotoxic compound for gastric cancer therapy, with lower cytotoxicity than cisplatin and less genotoxicity than cisplatin.

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Novel 1,3,4-thiadiazole derivatives show potent anti-proliferative activities against human leukemia and breast cancer cell lines, with compound 5b showing better activity than gossypol.

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Micelles catalyze an efficient, novel, and concise one-pot regio- and chemoselective synthesis of benzo[a]phenazines and naphtho[2,3-d]imidazoles in H2O, with excellent yields.

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New ruthenium(II) complexes show DNA binding, antioxidative activity, and cytotoxic activity against selected cancer cells.