Synthesis and cytotoxic evaluation of 7-chloro-4-phenoxyquinolines with formyl, oxime and thiosemicarbazone scaffolds

New 7-chloro-4-phenoxyquinoline derivatives bearing formyl, oxime and thiosemicarbazone functional groups were easily prepared using 4,7-dichloroquinoline and functionalized phenols as inexpensive and commercially available starting materials. Their chemical structures were confirmed by use of infra...

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Bibliographic Details
Published in:Medicinal chemistry research 2016-11, Vol.25 (11), p.2718-2727
Main Authors: Kouznetsov, Vladimir V., Sojo, Felipe, Rojas-Ruiz, Fernando A., Merchan-Arenas, Diego R., Arvelo, Francisco
Format: Article
Language:English
Subjects:
Biochemistry
Biomedical and Life Sciences
Biomedicine
Cell Biology
Chemical synthesis
Cytotoxicity
Dermis
Functional groups
NMR
Nuclear magnetic resonance
Original Research
Pharmacology/Toxicology
Phenols
Quinoline
Toxicity
Tumor cell lines
Tumor cells
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Summary:New 7-chloro-4-phenoxyquinoline derivatives bearing formyl, oxime and thiosemicarbazone functional groups were easily prepared using 4,7-dichloroquinoline and functionalized phenols as inexpensive and commercially available starting materials. Their chemical structures were confirmed by use of infrared and 1 H, 13 C nuclear magnetic resonance experiments. All the synthesized compounds were evaluated for their cytotoxicity against the cell lines MCF-7, SKBR-3, PC3, HeLa and human dermis fibroblast as non-tumor cells, in vitro using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) for assay. The quinoline derivatives 3a and 3d resulted as promising models for antitumor drugs, displaying good cytotoxic activity against four human cancer cell lines (9.18 µM 
ISSN:1054-2523
1554-8120
DOI:10.1007/s00044-016-1688-6