1160163-29-0Relevant academic research and scientific papers
Novel benzofuroxan derivatives against multidrug-resistant Staphylococcus aureus strains: Design using Topliss' decision tree, synthesis and biological assay
Jorge, Salomao Doria,Palace-Berl, Fanny,Masunari, Andrea,Cechinel, Cleber Andre,Ishii, Marina,Pasqualoto, Kerly Fernanda Mesquita,Tavares, Leoberto Costa
supporting information; experimental part, p. 5031 - 5038 (2011/10/05)
The aim of this study was the design of a set of benzofuroxan derivatives as antimicrobial agents exploring the physicochemical properties of the related substituents. Topliss' decision tree approach was applied to select the substituent groups. Hierarchical cluster analysis was also performed to emphasize natural clusters and patterns. The compounds were obtained using two synthetic approaches for reducing the synthetic steps as well as improving the yield. The minimal inhibitory concentration method was employed to evaluate the activity against multidrug-resistant Staphylococcus aureus strains. The most active compound was 4-nitro-3-(trifluoromethyl)[N′-(benzofuroxan-5-yl) methylene]benzhydrazide (MIC range 12.7-11.4 μg/mL), pointing out that the antimicrobial activity was indeed influenced by the hydrophobic and electron-withdrawing property of the substituent groups 3-CF3 and 4-NO2, respectively.
Design, synthesis, antimicrobial activity and molecular modeling studies of novel benzofuroxan derivatives against Staphylococcus aureus
Jorge, Salomao Doria,Masunari, Andrea,Rangel-Yagui, Carlota Oliveira,Pasqualoto, Kerly Fernanda Mesquita,Tavares, Leoberto Costa
experimental part, p. 3028 - 3036 (2009/09/08)
Molecular modification is a quite promising strategy in the design and development of drug analogs with better bioavailability, higher intrinsic activity and less toxicity. In the search of new leads with potential antimicrobial activity, a new series of 14 4-substituted [N′-(benzofuroxan-5-yl)methylene]benzohydrazides, nifuroxazide derivatives, were synthesized and tested against standard and multidrug-resistant Staphylococcus aureus strains. The selection of the substituent groups was based on physicochemical properties, such as hydrophobicity and electronic effect. These properties were also evaluated through the lipophilic and electrostatic potential maps, respectively, considering the compounds with better biological profile. Twelve compounds exhibited similar bacteriostatic activity against standard and multidrug-resistant strains. The most active compound was the 4-CF3 substituted derivative, which presented a minimum inhibitory concentration (MIC) value of 14.6-13.1 μg/mL, and a Clog P value of 1.87. The results highlight the benzofuroxan derivatives as potential leads for designing new future antimicrobial drug candidates.
