Synthesis and antitumor activity of some new phthalimide analogues

The reactive intermediate 1-(chloroalkyl)-1-aza-2-azoniaallene salts 3, which were prepared by treatment of the alpha,alpha'-dichloroazo derivatives 2 with SbCl5, underwent cycloaddition with the N-cyanoalkyl phthalimide compounds 4 and afforded the 1,2,4-triazolium salts 5. These salts rearranged spontaneously to the protonated 1,2,4-triazoles 6, followed by hydrolysis in situ to the 1,2,4-triazolo-alkyl-phthalimide compounds 7. The newly synthesized compounds were then evaluated for their antitumor activity in three cell lines.