Catálogo de Investigaciones | 2011-2012

51 Catálogo de Investigaciones | Pontificia Universidad Católica de Puerto Rico Synthesis of bisnitriles as precursors of aromatic diamidines using ketone, hydroxymethylene and ether as linker between two aromatic rings The aromatic diamidines have pharmacological properties that have been studied for years. These studies have shown that they can become potential therapeutic agents such as antimicrobials. Moreover, these agents are equally effective as anti parasites. This work involves the synthesis of bisnitriles, which is the first step in the synthesis pathway to generate different aromatic diamidines with a liker between two aromatic rings that are believed to have some affinity with the DNA. The problem to solve is to synthesize a varie t y of bisnitriles that will be later used in the synthesis of diamidines. These diamidines will be submitted to DNA affinity and biological activity studies. Reactions were performed refluxing at high and low temperature. Thin Layer Chromatography (TLC) was used to confirm reactions completion. Recrystallization was used for purification. For the synthesis of the bisnitrile with the ketone linker an appropriate dibromoketone, potassium ferrocyanide, sodium carbonate, palladium chloride, dimethylacetamide (DMA) and ethanol were allowed to react. After the distillation of the product, column purification the obtained ketonebisnitrile was submitted to a reduction reaction in methanol and NaBH4 to generating the bisnitrile with hydroxymethylene linker. To characterize the compounds the melting point (mp) and Nuclear Magnetic Resonance (NMR) were performed. 4,4-dicyanobenzophenone was obtained in 66.9% yield, mp 164°C- 165°C. 4,4-(hydroxymethylene)bisbenzonitrile showed purity with a mp of 105°C-108°C and 84% yield. sonivette colón mentor dra. adalgisa batista synthesis diamidines