A Dimroth rearrangement approach for the synthesis of selenopheno[2,3-e][1,2,4]triazolo[1,5-c]pyrimidines with cytotoxic activity on breast cancer cells.

Abstract

New selenopheno[2,3-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives have been synthesized via Dimroth rearrangement by cyclocondensation of 7-cyano-4-hydrazinyl-6-(pyrrolidin-1-yl)selenopheno[3,2-d]pyrimidine with electrophilic carbons of either orthoesters in acetic acid or carbon disulfide in pyridine followed by S-alkylation. All the newly synthesized products have been structurally elucidated. The in vitro anticancer screening of the tricyclic Se-containing heterocycles was accomplished against human breast carcinoma MCF-7 cancerous cell line and L929 cells. Anticancer results revealed that the S-hexyl-substituted compound with an IC50 value of 158.9µM in 72h was foremost among others in cytotoxic potency. In the following order, S-pentyl and S-ethyl-substituted derivatives with IC50 values of 216.1 and 396.5µM were second and third efficient compounds as in anticancer activity, respectively. The inhibitory effects of the mentioned compounds were less on the growth of L929 cells.