Molecules 2018, 23, 1396
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N-(1-Hydroxy-9-oxo-9H-xanthen-3-yl)-[1,10-biphenyl]-4-sulfonamide (15a). Yield: 60%. Yellow solid.
◦
M.p = 234–235 C. Rf = 0.56 (Petroleum ether: Acetone = 4:1). 1H NMR (400 MHz, DMSO-d6)
δ 12.67 (s, 1H),
11.40 (s, 1H), 8.10 (d, J = 7.6 Hz, 1H), 8.00 (d, J = 8.2 Hz, 2H), 7.93 (d, J = 8.1 Hz, 2H), 7.87 (t, J = 7.8 Hz, 1H),
7.71 (d, J = 7.8 Hz, 2H), 7.63 (d, J = 8.5 Hz, 1H), 7.54 – 7.36 (m, 4H), 6.81 (d, J = 1.8 Hz, 1H),
6.58 (d, J = 1.9 Hz, 1H). 13C NMR (151 MHz, DMSO)
δ 180.18, 161.88, 156.55, 155.41, 145.99, 144.88,
138.02, 137.76, 136.02, 129.03, 128.62, 127.75, 127.28, 127.02, 125.16, 124.57, 119.80, 117.81, 104.30, 99.02,
95.35. MS (ESI−) m/z 442.1 (M
found: 442.0716.
−
H)−. HRMS (ESI−): Calcd. for C25H16NO5S− [M
−
H]− m/z: 442.0705,
N-(1-Hydroxy-5-methoxy-9-oxo-9H-xanthen-3-yl)-[1,10-biphenyl]-4-sulfonamide (15b). Yield: 47%.
◦
Yellow solid. M.p = 220–221 C. Rf = 0.36 (Petroleum ether: Acetone = 4:1). 1H NMR (400 MHz, DMSO-d6)
12.66 (s, 1H), 11.42 (s, 1H), 8.01–7.89 (m, 5H), 7.72 (d, J = 7.7 Hz, 2H), 7.50 (q, J = 8.1, 7.5 Hz, 4H),
7.45–7.34 (m, 1H), 6.80 (s, 1H), 6.58 (s, 1H), 3.97 (s, 3H). 13C NMR (151 MHz, DMSO)
180.21, 161.79,
δ
δ
156.30, 147.88, 145.89, 145.44, 144.87, 138.00, 137.74, 129.02, 128.62, 127.77, 127.21, 127.02, 124.27, 120.56,
116.96, 115.58, 104.28, 99.13, 95.46, 56.21. MS (ESI−) m/z 471.8 (M
C26H18NO6S− [M − H]− m/z: 472.0860, found: 472.0878.
−
H)−. HRMS (ESI−): Calcd. for
N-(1-Hydroxy-5-methyl-9-oxo-9H-xanthen-3-yl)-[1,10-biphenyl]-4-sulfonamide (15c).
Yield: 48%.
Yellow solid. M.p = 235–237 C. Rf = 0.50 (Petroleum ether: Acetone = 4:1). 1H NMR (400 MHz,
DMSO-d6) 12.72 (s, 1H), 11.38 (s, 1H), 8.00 (d, J = 8.4 Hz, 2H), 7.96–7.88 (m, 3H), 7.72 (t, J = 7.9 Hz, 3H),
7.49 (t, J = 7.1 Hz, 2H), 7.43 (d, J = 6.6 Hz, 1H), 7.36 (t, J = 7.7 Hz, 1H), 6.83 (s, 1H), 6.59 (s, 1H), 2.48 (s, 3H).
◦
δ
13C NMR (151 MHz, DMSO)
δ 180.38, 161.75, 156.36, 153.68, 145.88, 144.79, 137.95, 137.74, 136.61, 128.97,
128.56, 127.67, 127.19, 126.95, 126.74, 123.93, 122.68, 119.55, 104.05, 99.03, 95.57, 15.06. MS (ESI−) m/z 456.1
(M − H)−. HRMS (ESI−): Calcd. for C26H18NO5S− [M − H]− m/z: 456.0911, found: 456.0926.
N-(1-Hydroxy-7-methoxy-9-oxo-9H-xanthen-3-yl)-[1,10-biphenyl]-4-sulfonamide (15d).
Yield: 58%.
Yellow solid. M.p = 220–222 ◦C. Rf = 0.33 (Petroleum ether: Acetone = 4:1). 1H NMR (400 MHz, DMSO-d6)
12.62 (s, 1H), 11.28 (s, 1H), 7.95–7.77 (m, 4H), 7.70–7.55 (m, 2H), 7.45–7.26 (m, 6H), 6.71 (s, 1H), 6.48 (s, 1H),
δ
3.77 (s, 3H). 13C NMR (151 MHz, DMSO)
δ 179.82, 161.68, 156.45, 155.70, 150.07, 145.72, 144.81, 137.95, 137.70,
128.96, 128.56, 127.68, 127.20, 126.95, 124.93, 120.11, 119.34, 105.03, 103.91, 98.80, 95.13, 55.63. MS (ESI−) m/z
471.9 (M − H)−. HRMS (ESI−): Calcd. for C26H18NO6S− [M − H]− m/z: 472.0860, found: 472.0873.
N-(1-Hydroxy-7-methyl-9-oxo-9H-xanthen-3-yl)-[1,10-biphenyl]-4-sulfonamide (15e).
Yield: 60%.
Yellow solid. M.p = 239–240. Rf = 0.48 (Petroleum ether: Acetone = 4:1). 1H NMR (400 MHz,
DMSO-d6) 12.72 (s, 1H), 11.39 (s, 1H), 7.99 (d, J = 8.4 Hz, 2H), 7.93 (d, J = 8.5 Hz, 2H), 7.87 (s, 1H),
7.71 (d, J = 7.2 Hz, 2H), 7.66 (d, J = 8.7 Hz, 1H), 7.56–7.33 (m, 4H), 6.79 (d, J = 1.8 Hz, 1H),
6.56 (d, J = 1.7 Hz, 1H), 2.40 (s, 3H). 13C NMR (151 MHz, DMSO)
180.10, 161.81, 156.47, 153.59, 145.80,
δ
δ
144.80, 137.95, 137.71, 137.−01, 134.02, 128.96, 12−8.55, 127.68, 1−27.21, 126.95, 124.29, 119.36, 117.55, 1−04.20,
−
98.84, 95.22, 20.12. MS (ESI ) m/z 456.1 (M
456.0911, found: 456.0928.
−
H) . HRMS (ESI ): Calcd. for C26H18NO5S [M
−
H] m/z:
N-(7-Chloro-1-hydroxy-9-oxo-9H-xanthen-3-yl)-[1,10-biphenyl]-4-sulfonamide (15f).
Yield: 58%.
Yellow solid. M.p = 259–260 C. Rf = 0.38 (Petroleum ether: Acetone = 4:1). 1H NMR (400 MHz, DMSO-d6)
◦
δ
12.42 (s, 1H), 11.45 (s, 1H), 8.05–7.95 (m, 3H), 7.96–7.86 (m, 3H), 7.75–7.66 (m, 3H), 7.49 (t, J = 7.3 Hz, 2H),
7.43 (d, J = 7.4 Hz, 1H), 6.81 (d, J = 2.0 Hz, 1H), 6.59 (d, J = 2.0 Hz, 1H). MS (ESI−) m/z 476.0 (M
−
H)−.
HRMS (ESI−): Calcd. for C25H15ClNO5S− [M − H]− m/z: 476.0365, found: 476.0379.
N-(7-Fluoro-1-hydroxy-9-oxo-9H-xanthen-3-yl)-[1,10-biphenyl]-4-sulfonamide (15g).
Yield: 51%.
Yellow solid. M.p = 250–252 C. Rf = 0.45 (Petroleum ether: Acetone = 4:1). 1H NMR (400 MHz,
DMSO-d6) 12.46 (s, 1H), 11.45 (s, 1H), 7.99 (d, J = 8.4 Hz, 2H), 7.93 (d, J = 8.8 Hz, 2H),
7.82–7.68 (m, 5H), 7.56–7.36 (m, 3H), 6.81 (s, 1H), 6.58 (s, 1H). 13C NMR (151 MHz, DMSO)
179.36,
◦
δ
δ
161.61, 158.10 (d, J = 243.9 Hz), 156.53, 151.81, 146.17, 144.83, 137.93, 137.67, 128.97, 128.57, 127.69, 127.21,
126.96, 123.81 (d, J = 24.7 Hz), 120.76 (d, J = 7.4 Hz), 120.40 (d, J = 7.9 Hz), 109.78 (d, J = 24.3 Hz), 103.86,