Síntese, caracterização e avaliação biológica de fenilhidrazonas derivadas de análogos da curcumina

Abstract

Several mono-carbonyl curcumin analogues are described in the literature, presenting numerous and pronounced biological activities, namely: antitumor, antioxidant, anti-inflammatory, anti-angiogenesis, among others. From these analogues are derived compounds containing the functionality hydrazone, which also present a variety of biological activities such as: anti-inflammatory, antitumor, analgesic, among others. In order to develop new molecules that can act as antioxidant, anticancer, anti-inflammatory, antitubercular, antimalarial and schistosomicidal agents, this work aimed at the synthesis and characterization of mono-carbonyl curcumin analogues and their phenylhydrazones containing in their structures donor groups, withdrawing electron and alkylated aliphatic chains of 8, 9, 10 and 12 carbons in the para position of the aromatic rings for further biological evaluation of them. We obtained thirteen mono-carbonyl curcumin analogues by aldol condensation reactions in basic and acidic media using acetone as reagents and different aromatic aldehydes, alkyl and heteroaromatic. To obtain of the alkylated curcumin analogues, were used as the starting material p-hydroxybenzaldehyde, which was submitted to the alkylation reaction using alkyl halides 1-chlorooctane, 1-bromononane, 1-chlorodecane and 1-chlorododecane as alkylating agents. We obtained from fifteen phenylhydrazones curcumin derivatives previously prepared by nucleophilic addition reactions in acidic media using reagents such as 2,4- dinitrophenylhydrazine and 4-nitrophenylhydrazine. The structures of the products obtained were elucidated by their infrared, UV-visible, 1H and 13C NMR spectra. Some analogues of curcumin and phenylhydrazones were submitted to antioxidant, anticancer, antibacterial, anti-inflammatory, antimalarial and schistosomicidal assays.