Design of new hybrids indole/phthalimide/oxadiazole-1,2,3 triazole agents and their anticancer properties

Abstract

A series of a new hybrid compounds combining 1,2,3-triazole with oxadiazolyl, Phthalimidyl or indolyl moiety has been synthesized. The reaction of our starting compound 5-phenyl-1-(aryl)-1H-1,2,3-triazole-4-carbohydrazides (5) with 5-nitrofuran-2-carboxylic acid (6) in refluxing phosphorous oxychloride afforded 2-nitro-5-(5-phenyl-1-(aryl)-1H-1,2,3-triazol-4-yl)-1,3,4-oxadiazoles 7a-c in good yields. Treatment of 5 with phthalic anhydride (8) in glacial acetic acid afforded N-(1,3-dioxoisoindolin-2-yl)-5-phenyl-1-(aryl)-1H-1,2,3-triazole-4-carboxamide 9a-d, while the reaction of 5 with isatin in slight acidic medium furnished N'-(2-oxoindolin-3-ylidene)-5-phenyl-1-(aryl)-1H-1,2,3-triazole-4-carbohydrazides 11a-d in 88–90% yields. The chemical structures for the novel products were elucidated via NMR spectroscopy and confirmed by single crystal x-ray diffraction studied. Promising antiproliferation activity have been found in some of the synthesized compounds when tested against various human cancer cell lines (HCT-116, HepG2 and MCF-7).