The Reaction of Cyanoacetylhydrazine with Chloroacetone: Synthesis of 1,2,4-Triazine, 1,3,4-Oxadiazine and Their Fused Derivatives with Antitumor Activities

Abstract

The reaction of cyanoacetylhydrazine with chloroacetone gave the N-(1-chloropropan-2-ylidene)-2-cyanoacetohy- drazide. This compound reacted with either hydrazine hydrate or phenylhydrazine to give the corresponding 1,2,4-tri- azine derivatives. On the other hand, its reaction with either benzenediazonium chloride or benzaldehyde gave in each case the 1,3,4-oxadiazine derivatives. Moreover, the reaction of the cyanoacetylhydrazine with 2-boromocyclohexa- none gave the corresponding hydrazine-hydrozon derivative. The antitumor evaluation of the newly synthesized prod- ucts against three cancer cell lines, namely breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268) was recorded. Some of the tested compounds showed activities which was higher than the reference doxorubicin.