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.

An easy and efficient approach for the synthesis of highly regioselective functionalized dihydronaphthalen-1(2H)-one family of α-tetralones from functionalized tetralone precursors which derived from Morita-Baylis-Hillman (MBH) adducts as starting substrates has been developed. The target dihydronaphthalen-1(2H)-ones are obtained through the oxidation of tetrahydronaphthalenes (THN) using DDQ as the oxidizing agent, conducted in aqueous acetic acid at reflux conditions. The yields obtained ranged from 90 to 98%. The resulting dihydronaphthalen-1(2H)-ones were evaluated for their in vitro antibacterial activity against nine Gram-positive and six Gram-negative strains. Additionally, their antifungal properties were assessed against three fungal pathogens by using the microdilution method and Biolog Phenotype Microarrays technology. Remarkably, the synthesized dihydronaphthalen-1(2H)-ones exhibited good antibacterial activity when compared to reference drugs such as vancomycin and ampicillin. Similarly, their antifungal activity is comparable to the effectiveness of the reference drugs cycloheximide and fluconazole.

A synthesis and theoretical study of 3-(2-methyl-1 H -indol-3-yl)-6-nitrophthalonitrile ( 1 ) are presented in this study. Structural confirmation of the molecule was achieved using ¹ H, ¹³ C NMR and mass spectroscopy. The determination of the atropisomer rotational barrier for compound 1 revealed its classification as a class 1 atropisomer. Additionally, a comprehensive analysis was conducted, encompassing HOMO–LUMO evaluation of the transition states, examination of their structure, and calculation of the activation energy.