Synthesis and biological evaluation of novel cytotoxic azanaphthoquinone annelated pyrrolo oximes

Two novel series of azanaphthoquinone annelated pyrrolo oximes were synthesized by aza-condensation. The cytotoxic evaluation on different cancer cell lines is reported and discussed comparing these two isomers. Two series of azanaphthoquinone annelated pyrrolo oximes have been synthesized. The anti...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2007-11, Vol.17 (22), p.6091-6095
Main Authors: Shanab, Karem, Pongprom, Nipawan, Wulz, Eva, Holzer, Wolfgang, Spreitzer, Helmut, Schmidt, Peter, Aicher, Babette, Müller, Gilbert, Günther, Eckhard
Format: Article
Language:English
Subjects:
Anticancer compounds
Antineoplastic agents
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Apoptosis - drug effects
Biological and medical sciences
Caspases - drug effects
Cell Cycle - drug effects
Cell Line, Tumor
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
General aspects
HeLa Cells
Humans
Medical sciences
Mitoxantrone - analogs & derivatives
Mitoxantrone - chemical synthesis
Mitoxantrone - pharmacology
Molecular Structure
Naphthoquinones - chemical synthesis
Naphthoquinones - chemistry
Naphthoquinones - pharmacology
Oximes - chemical synthesis
Oximes - chemistry
Oximes - pharmacology
Pharmacology. Drug treatments
Pyrroles - chemical synthesis
Pyrroles - chemistry
Pyrroles - pharmacology
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Summary:Two novel series of azanaphthoquinone annelated pyrrolo oximes were synthesized by aza-condensation. The cytotoxic evaluation on different cancer cell lines is reported and discussed comparing these two isomers. Two series of azanaphthoquinone annelated pyrrolo oximes have been synthesized. The antiproliferative activities of 10 compounds were evaluated on at least four different cell lines. One series of pyrrolo derivatives showed high cytotoxic activity. The effects on cell cycle and caspase activity were investigated. Compounds 9a and 9b showed an accumulation of cells in G2/M phase. Substantial and dose-dependent caspase activity was found after treatment of cells with 9a and 9b. This indicates an apoptosis inducing property of these compounds.
ISSN:0960-894X
0968-0896
1464-3405
1464-3391
DOI:10.1016/j.bmcl.2007.09.054