Details

Autor(en) / Beteiligte

• Jorge, Salomão Dória
• Masunari, Andrea
• Rangel-Yagui, Carlota Oliveira
• Pasqualoto, Kerly Fernanda Mesquita
• Tavares, Leoberto Costa

Titel

Design, synthesis, antimicrobial activity and molecular modeling studies of novel benzofuroxan derivatives against Staphylococcus aureus

Ist Teil von

• Bioorganic & medicinal chemistry, 2009-04, Vol.17 (8), p.3028-3036

Ort / Verlag

Amsterdam: Elsevier Ltd

Erscheinungsjahr

2009

Quelle

MEDLINE

Beschreibungen/Notizen

• A new series of 14 4-substituted [ N′-(benzofuroxan-5-yl)methylene] benzohydrazides with structure analogous of nifuroxazide were synthesized and tested against standard and multidrug-resistant Staphylococcus aureus strains. 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-CF 3 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.