Investigating a series of anilinoquinazoline derivatives substituted by carbamic acid esters, we have established the importance of the carbamate functional group and the substitution on the arylamino ring by a donor/acceptor group such as halide or methyl. All the newly-synthesized compounds described were evaluated for both their in vitro EGFR and VEGFR-2 kinase inhibition and antiproliferative activities against various cancer cells. These novel compounds were effective tyrosine kinase inhibitors (TKIs) for these two enzymes with in vitro IC50 values in the submicromolar range, but showed a moderated inhibitory activity on cancer cells. Modification of the ether linkage at the 6 or 7- position of the quinazoline core with a basic or aliphatic side chain (70–80) was investigated and it was demonstrated that introduction of aminoalkyl substituents such as morpholinoethoxy is a key modification that increases antiproliferative activity.