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Design and synthesis of new hybrids from a 1,2,4-triazole, prepared from piperine, and known nitroimidazolic drugs
Afonso Santine Magalhães Mesquita Velez
Universidade Federal Rural do Rio de Janeiro
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Crie um tópicoChagas disease (American trypanosomiasis) is a parasitosis caused by the protozoan Trypanosoma cruzi. The vectorial transmission route has the insect known as “kissing bug” (Triatoma infestans) as the main agent. According to WHO data, this parasitosis is part of a group of diseases called neglected tropical diseases, which is the most neglected. Currently, the therapeutic arsenal for the treatment of chagasic patients is very limited, with only two drugs, both of which are nitroheterocyclic derivatives, Nifurtimox and Benzonidazole; These two drugs are very limited and inefficient in the chronic phase of the disease, causing severe side effects, Our research group reported the trypanocidal effects of natural piperine and several of its derivatives. Recently, piperine’s heterocyclic derivatives bearing a 1,2,4 triazolic ring were described as having important anti-T. cruzi effects. The molecular planning developed here in was based on the molecular hybridization of 1,2,4-triazole core from piperine and the nitroimidazole portion of the know nitroheterocyclic drugs benzonidazole and metronidazole, present in both with well-described antiparasitic activity; aiming to enhance its activity through the synthesis of two novel hybrids that can act through two distinct mechanisms of action on parasite’s cell. The new hybrids were prepared in good yields from natural piperine and and they were characterized by the methods of analysis; highlighting the main signals signals of the NMR 1H and 13C spectra, which confirm the synthesis of these hybrids, in δ 3,62 ppm (t, 2H); δ 45,22 ppm and δ 3,63 ppm (t, 2H); δ 48,59 ppm which characterize the bond formed between CH2 and Sulfur for hybrids. The assessment of toxic effects of the novel hybrids against T. cruzi amastigotes (Tulahuen C2C4 LacZ strain) is underway in our laboratory.
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