Facile synthesis of N’-(anthracen-9(10H)-ylidene)-4-(4- hydrophenyl)-6-methyl-2-oxo-1,2,3,4-tetra hydropyrimidine- 5-carbohydrazide and other derivatives

Abstract

Pyrimidine as vital constituents of nucleic acid is recognized for its role in the chemotherapy of AIDS. Hydrazide-hydrazones are important moieties with notable biological diversity in drug design. Thus, the aim of this present study is to synthetically couple these two frameworks together in order to achieve small molecular targets for possible development of improved therapeutic candidates. This was achieved in a domino reaction starting with one-pot three-component reaction to afford ethyl-4-(4-hydroxyphenyl)-6-methyl-2-oxo-1,2,3,4- tetrahydropyrimidine-5-carboxylate, 7 which upon treatment with hydrazine hydrate under acid-mediated condition gave 8,as an essential precursor and reactive intermediate. The expeditious condensation of intermediate 8 with various cyclic and straight chain ketones furnished N’-(anthracen-9(10H)-ylidene)-4-(4-hydrophenyl)-6-methyl-2-oxo-1,2,3,4- tetrahydropyrimidine-5 -carbohydrazide 9a and other 9b-i scaffolds as envisaged. The reaction progress was monitored by thin layer chromatography (TLC) and upon reaction completion, the purification process was carried out with recrystallization and/or column chromatography. The authenticity of the prepared products 9a-i was confirmed by spectroscopic means including IR, UV, 1H-NMR, 13C-NMR and DEPT-135 as well as analytical data. These final products are good candidates for further study as regards anti-plasmodial activity which are been developed and examined.