19731-20-5Relevant academic research and scientific papers
Designing and exploring active N′-[(5-nitrofuran-2-yl) methylene] substituted hydrazides against three Trypanosoma cruzi strains more prevalent in Chagas disease patients
De Azevedo, Ricardo Alexandre,Ferreira, Adilson Kleber,Jorge, Salomo Dria,Palace-Berl, Fanny,Pasqualoto, Kerly Fernanda Mesquita,Silva, Marcelo Nunes,Tavares, Leoberto Costa,Teixeira, Sarah Fernandes,Zingales, Bianca,Zorzi, Rodrigo Rocha
supporting information, p. 330 - 339 (2015/04/27)
Chagas disease affects around 8 million people worldwide and its treatment depends on only two nitroheterocyclic drugs, benznidazole (BZD) and nifurtimox (NFX). Both drugs have limited curative power in chronic phase of disease. Nifuroxazide (NF), a nitroheterocyclic drug, was used as lead to design a set of twenty one compounds in order to improve the anti-Trypanosoma cruzi activity. Lipinski's rules were considered in order to support drug-likeness designing. The set of N′-[(5-nitrofuran-2-yl) methylene] substituted hydrazides was assayed against three T. cruzi strains, which represent the discrete typing units more prevalent in human patients: Y (TcII), Silvio X10 cl1 (TcI), and Bug 2149 cl10 (TcV). All the derivatives, except one, showed enhanced trypanocidal activity against the three strains as compared to BZD. In the Y strain 62% of the compounds were more active than NFX. The most active compound was Ng€2-((5-nitrofuran-2-yl) methylene)biphenyl-4-carbohydrazide (C20), which showed IC50 values of 1.17 ± 0.12 μM; 3.17 ± 0.32 μM; and 1.81 ± 0.18 μ4M for Y, Silvio X10 cl1, and Bug 2149 cl10 strains, respectively. Cytotoxicity assays with human fibroblast cells have demonstrated high selectivity indices for several compounds. Exploratory data analysis indicated that primarily topological, steric/geometric, and electronic properties have contributed to the discrimination of the set of investigated compounds. The findings can be helpful to drive the designing, and subsequently, the synthesis of additional promising drugs against Chagas disease.
Exploring 5-nitrofuran derivatives against nosocomial pathogens: Synthesis, antimicrobial activity and chemometric analysis
Zorzi, Rodrigo Rocha,Jorge, Salomao Doria,Palace-Berl, Fanny,Pasqualoto, Kerly Fernanda Mesquita,Bortolozzo, Leandro De Sa,De Castro Siqueira, Andre Murillo,Tavares, Leoberto Costa
supporting information, p. 2844 - 2854 (2014/05/06)
The burden of nosocomial or health care-associated infection (HCAI) is increasing worldwide. According to the World Health Organization (WHO), it is several fold higher in low- and middle-income countries. Considering the multidrug-resistant infections, t
5-Nitro-2-furfuriliden derivatives as potential anti-Trypanosoma cruzi agents: Design, synthesis, bioactivity evaluation, cytotoxicity and exploratory data analysis
Palace-Berl, Fanny,Jorge, Salom?o Dória,Pasqualoto, Kerly Fernanda Mesquita,Ferreira, Adilson Kleber,Maria, Durvanei Augusto,Zorzi, Rodrigo Rocha,De Sá Bortolozzo, Leandro,Lindoso, José ?ngelo Lauletta,Tavares, Leoberto Costa
, p. 5395 - 5406 (2013/09/02)
The anti-Trypanosoma cruzi activity of 5-nitro-2-furfuriliden derivatives as well as the cytotoxicity of these compounds on J774 macrophages cell line and FN1 human fibroblast cells were investigated in this study. The most active compounds of series I and II were 4-butyl-[N′-(5-nitrofuran-2-yl) methylene] benzidrazide (3g; IC50 = 1.05 μM ± 0.07) and 3-acetyl-5-(4-butylphenyl)-2-(5-nitrofuran-2-yl)-2,3-dihydro,1,3,4-oxadiazole (4g; IC50 = 8.27 μM ± 0.42), respectively. Also, compound 3g was more active than the standard drugs, benznidazole (IC50 = 22.69 μM ± 1.96) and nifurtimox (IC50 = 3.78 μM ± 0.10). Regarding the cytotoxicity assay, the 3g compound presented IC 50 value of 28.05 μM (SI = 26.71) against J774 cells. For the FN1 fibroblast assay, 3g showed IC50 value of 98 μM (SI = 93.33). On the other hand, compound 4g presented a cytotoxicity value on J774 cells higher than 400 μM (SI >48), and for the FN1 cells its IC50 value was 186 μM (SI = 22.49). Moreover, an exploratory data analysis, which comprises hierarchical cluster (HCA) and principal component analysis (PCA), was carried out and the findings were complementary. The molecular properties that most influenced the compounds' grouping were C log P and total dipole moment, pointing out the need of a lipophilic/hydrophilic balance in the designing of novel potential anti-T. cruzi molecules.
Synthesis and biological activity of nifuroxazide and analogs. II
Tavares,Chiste,Santos,Penna
, p. 432 - 436 (2007/10/03)
Nifuroxazyde and six analogs were synthesized by varying the substitute from the para-position of the benzenic ring and the heteroatom of the heterocyclic ring. The MIC of seven resultant compounds was determined by serial dilutions, testing the ATCC 25923 strain of Staphylococcus aureus. A significant increase in the anti-microbial activity of thyophenic analogs, as compared with furanic and pyrrholic analogs, was observed. In addition, unlike the cyano and hydroxyl groups, the acetyl group promoted anti- microbial activity.
