2020
DOI: 10.1111/cbdd.13803
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Design, synthesis and activity against Staphylococcus epidermidis of 5‐chloro‐2‐ or 5‐chloro‐4‐methyl‐9H‐xanthen‐9‐one and some of its derivatives

Abstract: Ten new xanthone derivatives have been designed and synthesized for their potential antibacterial activity. All compounds have been screened against Staphylococcus epidermidis strains ATCC 12228 and clinical K/12/8915. The highest antibacterial activity was observed for compound 3: 5-chloro-2-((4-(2-hydroxyethyl)piperazin-1-yl) methyl)-9H-xanthen-9-one dihydrochloride, exhibiting MIC of 0.8 µg/ml against ATCC 12228 strain, compared to linezolid (0.8 µg/ml), ciprofloxacin (0.2 µg/ml) or trimethoprim and sulfame… Show more

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Cited by 4 publications
(9 citation statements)
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“…The first reaction was the Ullmann's condensation of 2,3‐dichlorobenzoic acid with p ‐cresol for compounds 1–6 and o ‐cresol for compounds 7–10 , respectively. In the second step, obtained products of condensation underwent the reaction of cyclization, performed in 98% H 2 SO 4 in 100°C for 3 h, in order to obtain 5‐chloro‐2‐methyl‐9 H ‐xanthen‐9‐one (Mazur et al, 2020) (for 1 – 6 ) or 5‐chloro‐4‐methyl‐9 H ‐xanthen‐9‐one (Mazur et al, 2020) (for 7 – 10 ). In the next step, obtained intermediate products underwent the reaction of free‐radical bromination of the methyl group with N ‐bromosuccinimide (NBS), performed in CCl 4 as a solvent, in the presence of benzoyl peroxide as a catalyst and under light, resulting in 5‐chloro‐2‐bromomethyl‐9 H ‐xanthen‐9‐one (Mazur et al, 2020) or 5‐chloro‐4‐bromomethyl‐9 H ‐xanthen‐9‐one,(Mazur et al, 2020) respectively.…”
Section: Resultsmentioning
confidence: 99%
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“…The first reaction was the Ullmann's condensation of 2,3‐dichlorobenzoic acid with p ‐cresol for compounds 1–6 and o ‐cresol for compounds 7–10 , respectively. In the second step, obtained products of condensation underwent the reaction of cyclization, performed in 98% H 2 SO 4 in 100°C for 3 h, in order to obtain 5‐chloro‐2‐methyl‐9 H ‐xanthen‐9‐one (Mazur et al, 2020) (for 1 – 6 ) or 5‐chloro‐4‐methyl‐9 H ‐xanthen‐9‐one (Mazur et al, 2020) (for 7 – 10 ). In the next step, obtained intermediate products underwent the reaction of free‐radical bromination of the methyl group with N ‐bromosuccinimide (NBS), performed in CCl 4 as a solvent, in the presence of benzoyl peroxide as a catalyst and under light, resulting in 5‐chloro‐2‐bromomethyl‐9 H ‐xanthen‐9‐one (Mazur et al, 2020) or 5‐chloro‐4‐bromomethyl‐9 H ‐xanthen‐9‐one,(Mazur et al, 2020) respectively.…”
Section: Resultsmentioning
confidence: 99%
“…In the second step, obtained products of condensation underwent the reaction of cyclization, performed in 98% H 2 SO 4 in 100°C for 3 h, in order to obtain 5‐chloro‐2‐methyl‐9 H ‐xanthen‐9‐one (Mazur et al, 2020) (for 1 – 6 ) or 5‐chloro‐4‐methyl‐9 H ‐xanthen‐9‐one (Mazur et al, 2020) (for 7 – 10 ). In the next step, obtained intermediate products underwent the reaction of free‐radical bromination of the methyl group with N ‐bromosuccinimide (NBS), performed in CCl 4 as a solvent, in the presence of benzoyl peroxide as a catalyst and under light, resulting in 5‐chloro‐2‐bromomethyl‐9 H ‐xanthen‐9‐one (Mazur et al, 2020) or 5‐chloro‐4‐bromomethyl‐9 H ‐xanthen‐9‐one,(Mazur et al, 2020) respectively. The final step was aminolysis of the appropriate bromo‐substituted derivative by means of commercially available aminoalkanols: 2‐(methylamino)ethan‐1‐ol for 1 and 7 , D,L ‐ trans ‐piperidin‐3‐ol for 2 , piperidin‐4‐ol for 3 and 10 , D,L ‐ trans ‐2‐aminocyclohexan‐1‐ol for 4 , trans ‐4‐aminocyclohexan‐1‐ol for 5 , R,S ‐azepan‐4‐ol for 6 , R,S ‐2‐aminopropan‐1‐ol for 8 and R,S ‐2‐aminobutan‐1‐ol for 9 .…”
Section: Resultsmentioning
confidence: 99%
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