Synthesis of benzo-annulated tryptanthrins and their biological properties

A series of benzo-annulated tryptanthrins were prepared and their physicochemical and biological properties were evaluated. Tryptanthrin and its benzo-annulated derivatives showed selective inhibitory activity on topo I with significant cytotoxicity against selected human cancer cell lines. A series...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2012-08, Vol.20 (16), p.4962-4967
Main Authors: Liang, Jing Lu, Park, So-Eun, Kwon, Youngjoo, Jahng, Yurngdong
Format: Article
Language:English
Subjects:
3-Amino-2-naphthoic acid
alkaloids
Animals
Benzotryptanthrin
Biological and medical sciences
Cattle
Cytotoxicity
DNA - metabolism
DNA topoisomerase
DNA topoisomerase (ATP-hydrolysing)
DNA Topoisomerases, Type I - metabolism
DNA Topoisomerases, Type II - metabolism
Dose-Response Relationship, Drug
enzyme inhibitors
Isatin
Isatoic anhydride
Medical sciences
Molecular Structure
optical properties
Pharmacology. Drug treatments
Quinazolines - chemical synthesis
Quinazolines - chemistry
Quinazolines - pharmacology
redox potential
Redox properties
Structure-Activity Relationship
synthesis
Topoisomerase I
Topoisomerase I Inhibitors - chemical synthesis
Topoisomerase I Inhibitors - chemistry
Topoisomerase I Inhibitors - pharmacology
Topoisomerase II
Topoisomerase II Inhibitors - chemical synthesis
Topoisomerase II Inhibitors - chemistry
Topoisomerase II Inhibitors - pharmacology
Tryptanthrin
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Summary:A series of benzo-annulated tryptanthrins were prepared and their physicochemical and biological properties were evaluated. Tryptanthrin and its benzo-annulated derivatives showed selective inhibitory activity on topo I with significant cytotoxicity against selected human cancer cell lines. A series of benzo-annulated derivatives of tryptanthrin were prepared and their optical and redox properties were studied. Tryptanthrin and its benzo-annulated derivatives showed selective inhibitory activity on topo I with an increase of activity on topo II by benzo-annulation on quinazolin-4(3H)-one moiety. Although the benzo-annulation on quinazolin-4(3H)-one ring did not affect significantly on the inhibitory activities against topo I and II, the benzoannulation on indolin-3-one ring affected the inhibitory activity very much especially by linear annulation. Cytotoxicities were not significantly changed upon benzoannulation, which were not directly related either to the inhibitory activities against topo I and II or to the reduction potentials.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2012.06.034