Regioselective\nOxidation of Tetrahydronaphthalenes\nto α‑Tetralone Derivatives Using DDQ as Oxidizing Agent:\nSynthesis and Evaluation of Antibacterial and Antifungal Activities

An easy and efficient approach for the synthesis of highly\nregioselective\nfunctionalized dihydronaphthalen-1(2<i>H</i>)-one family\nof α-tetralones from functionalized tetralone precursors which\nderived from Morita–Baylis–Hillman (MBH) adducts as\nstarting substrates has been developed. The target dihydronaphthalen-1(2<i>H</i>)-ones are obtained through the oxidation of tetrahydronaphthalenes\n(THN) using DDQ as the oxidizing agent, conducted in aqueous acetic\nacid at reflux conditions. The yields obtained ranged from 90 to 98%.\nThe resulting dihydronaphthalen-1(2<i>H</i>)-ones were evaluated\nfor their <i>in vitro</i> antibacterial activity against\nnine Gram-positive and six Gram-negative strains. Additionally, their\nantifungal properties were assessed against three fungal pathogens\nby using the microdilution method and Biolog Phenotype Microarrays\ntechnology. Remarkably, the synthesized dihydronaphthalen-1(2<i>H</i>)-ones exhibited good antibacterial activity when compared\nto reference drugs such as vancomycin and ampicillin. Similarly, their\nantifungal activity is comparable to the effectiveness of the reference\ndrugs cycloheximide and fluconazole.