N-Phenethyl and N-naphthylmethyl isatins and analogues as in vitro cytotoxic agents

A range of N-phenethyl, N-phenacyl, and N-(1- and 2-naphthylmethyl) derivatives of 5,7-dibromoisatin 2 were prepared by N-alkylation reactions. Their activity against human monocyte-like histiocytic lymphoma (U937), leukemia (Jurkat), and breast carcinoma (MDA-MB-231) cell lines was assessed. The re...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2008-03, Vol.16 (6), p.3118-3124
Main Authors: Matesic, Lidia, Locke, Julie M., Bremner, John B., Pyne, Stephen G., Skropeta, Danielle, Ranson, Marie, Vine, Kara L.
Format: Article
Language:English
Subjects:
Alkylation
Antineoplastic agents
Antineoplastic Agents - chemistry
Biological and medical sciences
Breast Neoplasms - drug therapy
Cancer
Cell Line, Tumor
Cytotoxins
Female
General aspects
Humans
Inhibitory Concentration 50
Isatin - analogs & derivatives
Isatin - chemistry
Isatin - pharmacology
Isatins
Leukemia - drug therapy
Lymphoma - drug therapy
Male
Medical sciences
Pharmacology. Drug treatments
Structure-Activity Relationship
Tubulin polymerization inhibitors
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Summary:A range of N-phenethyl, N-phenacyl, and N-(1- and 2-naphthylmethyl) derivatives of 5,7-dibromoisatin 2 were prepared by N-alkylation reactions. Their activity against human monocyte-like histiocytic lymphoma (U937), leukemia (Jurkat), and breast carcinoma (MDA-MB-231) cell lines was assessed. The results allowed further development of structure–activity relationships. The compound 5,7-dibromo- N-(1-naphthylmethyl)-1 H-indole-2,3-dione 5a was the most potent against U937 cells with an IC 50 value of 0.19 μM.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2007.12.026