Various novel 5-( monosubstituted amino)-2-deoxo-2-phenyl-5-deazaflavins derivatives have been synthesized by direct coupling of 5-deazaflavins and N-alkyl or aryl amines. The antitumor activities against human tumor cell lines CCRF-HSB-2 and KB cells have been investigated in vitro and many compounds showed promising potential antitumor activities with less cytotoxicities. AutoDock molecular docking into PTK ( PDB code: 1t46) has been done for lead optimization of these compounds as potential PTK inhibitors. Some of the synthesized 5-( monosubstituted amino)-2-deoxo-2-phenyl-5-deazaflavins at the 5- position exhibited reasonable binding affinities into PTK with the hydrogen bond through their C5-NH moiety. (C) 2008 Elsevier Ltd. All rights reserved.