Anti-tumor and anti-leishmanial evaluations of 1,3,4-oxadiazine, pyran derivatives derived from cross-coupling reactions of beta-bromo-6H-1,3,4-oxadiazine derivatives

作者：Mohareb Rafat M^*; Schatz Juergen

来源：Bioorganic & Medicinal Chemistry, 2011, 19(8): 2707-2713.

DOI：10.1016/j.bmc.2011.02.051

• Cross-coupling
• Hydrazide-hydrazone
• 1,3,4-Oxadiazine
• Pyran
• Anti-tumor
• Anti-leishmanial

Cyanoacetylhydrazine reacted with the omega-bromoacetophenones 2a,b to give hydrazide-hydrazone derivatives 3a,b. The latter products were cyclized to the 1,3,4-oxadiazine derivatives 4a,b. Bromination of the latter products gave the 6-bromo-6H-1,3,4-oxadiazine derivatives 5a,b which underwent a series of cross-coupling reactions. The antitumor evaluation of the newly synthesized products against the three cancer cells namely breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268) showed that some of them have high inhibitory effect towards three cell lines which is higher than the standard. Moreover, the anti-leishmanial activity of the newly synthesized product was tested on Leishmania donovani amastigotes showed that some compounds have high activity.