Optimization of biaryloxazolidinone as promising antibacterial agents against antibiotic-susceptible and antibiotic-resistant gram-positive bacteria

Emergent antibacterial activity ofN-(thiazol-2-yl)benzenesulfonamides in conjunction with cell-penetrating octaarginine

“…Then organic layer was evaporated under vacuum and the resulting residue was nally puried by column chromatography to afford title compound 1 (80%). 1 30% hydrogen peroxide (H 2 O 2 , 7 mmol) was slowly added to a mixture of compound 1 (2 mmol) in acetic acid (5 mL). The reaction mixture was then heated at 50 C for 5-6 h. Aer completion of reaction, reaction mixture was cooled at room temperature and poured over crushed ice and extracted with DCM.…”

“…Organic layer was then washed with saturated NaHCO 3 solution, brine solution, dried over anhydrous Na 2 SO 4 and evaporated under vacuum to obtain crude solid residue which was nally puried using column chromatography to get desire compound 2 (75%). 1 Thiourea (0.39 mmol) and the crude residue obtained from the previous step was dissolved in ethanol (10 mL) and reuxed for 6 h. Aer completion of reaction, the reaction mixture was cooled at room temperature, poured in ice-cold water, and basied with saturated NaHCO 3 solution (pH 8-9) followed by extraction with diethyl ether. The organic layer was washed with saturated NaHCO 3 solution, brine solution and dried over anhydrous Na 2 SO 4 .…”

“…The organic layer was removed under reduced pressure and the resulting crude residue was further puried using the column chromatography to obtain title compound 4 as a yellow colored solid (80%). 1 We have recently reported the synthesis and SphK1 kinase inhibitory activity of phenylthiazolyl benzenesulfonamide derivatives. 39 Suitable sulfonyl chloride (1.1 mmol) was added to a solution of compound 4 (0.6 mmol) in dry pyridine (7-8 mL) and the resultant mixture was stirred for 5 hours at room temperature.…”

“…The title compound was synthesized as described above; yield 52%, 1 The title compound was synthesized as described above; yield 55%, 1 The title compound was synthesized as described above; yield 55%, 1…”

“…H NMR (CDCl 3 , 500 MHz): d 7.92 (d, 2H, J ¼ 7.5 Hz), 7.84 (d, 2H, J ¼ 8.0 Hz), 7.53 (d, 2H, J ¼ 8.0 Hz), 7.45 (d, 2H, J ¼ 8.0 Hz), 7.35-7.33 (m, 4H), 7.22 (d, 2H, J ¼ 6.5 Hz), 3.06 (s, 3H); 13 C NMR (CDCl 3 , 125 MHz): 167.2, 140.8, 140.6, 138.3, 134.4, 130.1, 129.9, 129.4, 129.2, 129.1, 129.1, 128.9, 127.9, 127.6, 122.4, 44.The title compound was synthesized as described above; yield 58%,1 H NMR (CDCl 3 , 500 MHz): d 7.95 (d, 2H, J ¼ 7.5 Hz), 7.86 (d, 2H, J ¼ 8.5 Hz), 7.56-7.50 (m, 3H), 7.46 (t, 2H, J ¼ 8.0 Hz), 7.38-7.31 (m, 3H), 7.22 (d, 2H, J ¼ 7.0 Hz), 3.04 (s, 3H); 13 C NMR (CDCl 3 , 125 MHz): 166.4, 141.5, 141.1, 134.6, 132.5, 130.2, 129.5, 129.4, 129.4, 129.1, 128.9, 128.1, 126.6, 122.9, 44.3; MS (ESI): m/ z: calculated [M + H] + : 471.0501; found [M + H] + : 471.0519.…”