Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 19, Issue 18, Pages 5291-5299Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2011.08.016
Keywords
DNA intercalator; Microwave chemistry; NMR spectroscopy; Molecular dynamics; Biological activity
Funding
- MIUR
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Bis-2,3-heteroarylmaleimides and polyheterocondensed imides joined through nitrogen atoms of the N, N'-bis(ethyl)-1,3-propanediamine linker were prepared from substituted maleic anhydrides and symmetrical diamines in good to satisfactory yields and short reaction times using microwave heating. The novel molecules were shown to inhibit proliferation of human tumor cells (NCI-H460 lung carcinoma) and rat aortic smooth muscle cells (SMCs) with variable potencies. Compound 11a, the most potent one of the series, showed IC50 values comparable to those observed for the leading molecule elinafide in both cell lines, but with a higher selectivity toward human tumor cells. Compound 11a affected G1/S phase transition of the cell cycle, showed in vitro DNA intercalating activity and in vivo antitumor activity. A thorough structural analysis of the 11a-DNA complex was also made by mean of NMR and computational techniques. (C) 2011 Elsevier Ltd. All rights reserved.
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