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Recently, we have reported a series of 4-anilino-6,7-dimethoxyquinazolines as tyrosine kinase inhibitors with interesting in vitro IC50 values for the Epidermal Growth Factor Receptor (EGFR) and/or for the Vascular Endothelial Growth Factor Receptor-2 (VEGFR-2). In this paper, we studied the impact of amino group in C-2 position of the quinazoline core on this series. The new synthesized compounds described herein were evaluated for both in vitro EGFR and VEGFR-2 kinase inhibition and antiproliferative activity in different cancer cell lines (PC3, HT29 and MCF7). 2-Aminoquinazolines substituted by a carbamic acid ester group present an interesting antiproliferative activity without tyrosine kinase inhibition. Thus, we drew the present study to explore the potential interaction of these molecules with the double-stranded DNA, the target of many conventional antitumor agents. We evaluated the strength and the way these molecules bind to DNA by UV-visible spectroscopy, circular dichroism, DNA thermal denaturation, and fluorescence measurements.