Synthesis, characterization and anticancer evaluation of novel tri-arm star shaped 1,3,5-triazine hydrazones

Abstract

A series of novel trisubstituted triazine hydrazones [N₃C₃(-OC₆H₄-p-CH=N-NH-C(O)-C₆H₄-p-X)₃] (X = H, Br, Cl, F, OH, OCH₃, CH₃, NO₂, NH₂) were prepared by a three-fold condensation reaction of 2,4,6-tris(4-formylphenoxy)-1,3,5-triazine with p-substituted benzoic acid hydrazides [NH₂-NH-C(O)-C₆H₄-p-X] with excellent yields. The structures were confirmed by elemental analysis, FT-IR, ¹H, ¹³C, 2D-HSQC NMR and mass spectrometry (MALDI-TOF). These derivatives bearing hydrolysable hydrazone linkages were evaluated for their in vitro antiproliferative activity against the human liver carcinoma cell line (HepG2) and human cervix carcinoma cell line (HeLa).