Synthesis and antitumor activities of some new 4-(1-naphthylmethylamino)-and 4-(1-naphtylmethylamino)-1,2,4-triazol-5-one derivatives

A series of 4-(1-naphthylidenamino)-1,2,4-triazol-5-one derivatives (3a-e) were synthesized by condensation of corresponding 3-alkyl-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones with 1-naphthaldehyde. Acetylation and alkylation of these compounds gave 4a-e and 5a-e, respectively. Sodium borohydride reduction of 1-naphthylidenamino derivatives afforded naphthylmethylamino derivatives, which were sub-sequently acetylated. Depending on the duration of the acetylation, mono or bis acetamide derivatives were obtained. The in vitro antitumor activities of some selected compounds were screened and compounds 3e, 5c, 6e and 9c were found to be active.