Synthesis and cytotoxic activities of 2-alkyl-2,3-dihydro-1H-2,6,9-triazacyclopenta[b]anthracene-5,10-diones

Kwak, Jae‐Hwan; Namgoong, Kwon; Jung, Jae‐Kyung; Cho, Jungsook; Kim, Hwan‐Mook; Park, Sung‐Gyu; Yoo, Yeong-Ah; Kwon, Joo-Hee; Lee, Heesoon

doi:10.1007/s12272-001-1258-6

Cited by 4 publications

(2 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Starting material 76a was treated with 2,3-dimethylbutadiene to give the cycloaddition adduct, which was directly aromatized by aerial oxidation in ethanolic KOH under reflux to give 6,7-dimethylbenzo[ g ]quinoxaline-5,10-dione 82 [ 66 , 67 ]. The required intermediate 82 was treated with N -bromosuccinimide (NBS) and a catalytic amount of benzoylperoxide under irradiation to give the corresponding bisbromomethyl product in 42% yield.…”

Section: Discussionmentioning

confidence: 99%

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

et al. 2020

View full text Add to dashboard Cite

Anthracycline antibiotics play an important role in cancer chemotherapy. The need to improve their therapeutic index has stimulated an ongoing search for anthracycline analogs with enhanced properties. This review aims to summarize the common synthetic approaches to benzo[g]quinoxaline-5,10-diones and their uses in heterocyclic chemistry. Because of the valuable biological activities of the 1,4-diazaanthraquinone compounds, a summary of the most promising heterocyclic quinones is provided together with their antitumor properties.

show abstract

Section: Discussionmentioning

confidence: 99%

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

et al. 2020

View full text Add to dashboard Cite

show abstract

“…The cytotoxic activity of six human cancer cells (HCT-15, SK-OV-3, A549, SNB19, MCF-7, and MCF-7/ADR) was evaluated in vitro. Compounds 156-160 showed significant inhibitory effects on all human cancer cell lines, with IC50 values ranging from 0.035 to 0.381 µM [142]. [4,5-b]phenazine-5,12-diones.…”

Section: Anthraquinone-and 14-naphtoquinone-pyrazine Hybridizationmentioning

confidence: 99%

Natural Products–Pyrazine Hybrids: A Review of Developments in Medicinal Chemistry

Chen,

Guo,

Quan

et al. 2023

Molecules

View full text Add to dashboard Cite

Pyrazine is a six-membered heterocyclic ring containing nitrogen, and many of its derivatives are biologically active compounds. References have been downloaded through Web of Science, PubMed, Science Direct, and SciFinder Scholar. The structure, biological activity, and mechanism of natural product derivatives containing pyrazine fragments reported from 2000 to September 2023 were reviewed. Publications reporting only the chemistry of pyrazine derivatives are beyond the scope of this review and have not been included. The results of research work show that pyrazine-modified natural product derivatives have a wide range of biological activities, including anti-inflammatory, anticancer, antibacterial, antiparasitic, and antioxidant activities. Many of these derivatives exhibit stronger pharmacodynamic activity and less toxicity than their parent compounds. This review has a certain reference value for the development of heterocyclic compounds, especially pyrazine natural product derivatives.

show abstract

Synthesis and in Vitro cytotoxic activities of 2-alkyl-2,3-dihydro-1H-2,6-diazacyclopenta[b]anthracene-5,10-diones

et al. 2010

Self Cite

View full text Add to dashboard Cite

A series of 2-alkyl-2,3-dihydro-1H-2,6-diazacyclopenta[b]anthracene-5,10-diones (4a-f) was synthesized and their in vitro cytotoxic activities were evaluated against six human cancer cell lines (HCT15, SK-OV-3, SNB19, A549, MCF7 and MCF7/ADR). They all appeared to be less potent than doxorubicin against all doxorubicin sensitive human cancer cell lines tested. However, these compounds retained considerable cytotoxic activity against the doxorubicin-resistant cell line MCF7/ADR, implying their therapeutic potential to treat doxorubicin-resistant tumors. The most active compound 4c was equipotent with doxorubicin against HCT15 cell line.

show abstract

Synthesis and cytotoxic activities of 2-alkyl-2,3-dihydro-1H-2,6,9-triazacyclopenta[b]anthracene-5,10-diones

Cited by 4 publications

References 10 publications

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

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

Natural Products–Pyrazine Hybrids: A Review of Developments in Medicinal Chemistry

Synthesis and in Vitro cytotoxic activities of 2-alkyl-2,3-dihydro-1H-2,6-diazacyclopenta[b]anthracene-5,10-diones

Contact Info

Product

Resources

About