Synthesis and cytotoxic activities of the amine-exchange products of 2-dimethylaminomethyl-5-(E)-substituted arylidene cyclopentanones with anilines: 2-arylaminomethyl-5-(E)-arylidene cyclopentanones.

A series of 2-arylaminomethyl, and 2-(4-morpholinylmethyl)-5-(E)-arylidene cyclopentanones have been synthesized via an amine-exchange reaction. Most of the compounds showed significant cytotoxic activities, in vitro, on various human cancer cell lines. Generally, compounds with a para-chloroanilino moiety were more active than those of other aniline derivatives. No apparent changes were observed by altering the substituents on the arylidene portion. For the majority of active compounds, leukemia is one of the most sensitive subpanels at both GI50 and TGI levels but the least sensitive one at the LC50 level. Colon cancer is one of the most sensitive subpanels in all three levels. COMPARE results indicated that the characteristics, and possibly the mechanism of the cytotoxic properties of the 2-arylaminomethyl derivatives might be different from that of the 2-dialkylaminomethyl derivatives previously reported.