RESUMO
The emergence of antibiotics-resistant bacteria has been a serious concern for medical professionals over the last decade. Therefore, developing new and effective antimicrobials with modified or different modes of action is a continuing imperative. In this context, our study focuses on evaluating the antimicrobial activity of different chemically synthesized flavonoids (FLAV) to guide the chemical synthesis of effective antimicrobial molecules. A set of 12 synthesized molecules (4 chalcones, 4 flavones and 4 flavanones), bearing substitutions with chlorine and bromine groups at the C6' position and methoxy group at the C4' position of the B-ring were evaluated for antimicrobial activity toward 9 strains of Gram-positive and Gram-negative bacteria and 3 fungal strains. Our findings showed that most tested FLAV exhibited moderate to high antibacterial activity, particularly against Staphylococcus aureus with minimum inhibitory concentrations (MIC) between the range of 31.25 and 125 µg/mL and that chalcones were more efficient than flavones and flavanones. The examined compounds were also active against the tested fungi with a strong structure-activity relationship (SAR). Interestingly, leakage measurements of the absorbent material at 260 nm and scanning electron microscopy (SEM) demonstrated that the brominated chalcone induced a significant membrane permeabilization of S. aureus.
RESUMO
The title compound, C(16)H(17)N(3)O(4), was prepared by the reaction of 5-nitro-2-(pyrrolidin-1-yl)benzaldehyde and ethyl cyano-acetate. The mol-ecular structure adopts an E conformation with respect to the C=C double bond. The five-membered ring has a half-chair conformation, with puckering parameters Q(2)= 0.399â (2)â Å and Ï = 93.1â (3)°. In the crystal, inversion dimers , linked by pairs of C-Hâ¯O inter-actions, are further connected through C-Hâ¯N hydrogen bonds. Weak slipped π-π inter-actions occur between symmetry-related benzene rings [centroid-centroid distance = 3.785â (1)Å].
