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F. Jin et al. / Bioorg. Med. Chem. 21 (2013) 5694–5706
(br, 1H), 3.92 (s, 2H), 3.80 (s, 6H), 3.51 (s, 2H), 3.25 (t, J = 4.6 Hz,
4H), 2.71 (d, J = 11.7 Hz, 2H), 2.20 (m, 2H), 1.99 (m, 4H). 13C NMR
J = 7.6 Hz, 5H), 7.24 (d, J = 5.3 Hz, 1H), 7.16 (dd, J = 8.4, 5.4 Hz,
2H), 6.94 (m, 3H), 6.44 (br, 1H), 3.51 (s, 2H), 3.41 (s, 2H), 3.28
(m, 4H), 2.76 (d, J = 11.4 Hz, 2H), 2.33–2.06 (m, 6H). 13C NMR
(101 MHz, CDCl3) d 173.78, 172.27, 164.49, 162.07 (J = 246.4 Hz),
150.53 (J = 34.3 Hz), 148.54, 137.75, 136.93, 132.60, 130.92
(J = 8.1 Hz), 130.56 (J = 3.0 Hz), 129.05, 128.38, 127.33, 121.12
(J = 275.7 Hz), 120.33, 115.70 (J = 21.2 Hz), 62.92, 58.71, 48.99,
42.58, 40.48, 39.28, 31.95. HRMS calcd for [M+H]+ 586.2442, found
586.2443.
(101 MHz, CDCl3)
d 173.94, 172.00, 167.27, 161.04, 156.91,
136.35, 133.95, 132.17, 131.26, 129.15, 128.72, 128.38, 128.20,
127.37, 126.63, 125.99, 125.68, 123.87, 105.25, 103.78, 62.83,
58.01, 55.64, 42.23, 41.48, 39.96, 39.36, 31.81. HRMS calcd for
[M+H]+ 609.3078, found 609.3073.
Compound 6d: White solid, yield 60%. 1H NMR (400 MHz,
DMSO-d6) d 8.00 (dd, J = 20.3, 8.1 Hz, 3H), 7.94–7.86 (m, 1H),
7.80 (t, J = 8.4 Hz, 3H), 7.67 (s, 1H), 7.49 (p, J = 6.9 Hz, 2H), 7.45–
7.21 (m, 9H), 3.83 (s, 2H), 3.44 (s, 2H), 3.13 (s, 4H), 2.63 (dt,
J = 16.4, 9.5 Hz, 4H), 2.24 (t, J = 11.0 Hz, 2H), 2.13 (d, J = 13.0 Hz,
2H), 1.95 (t, J = 10.8 Hz, 2H), 1.17 (t, J = 7.6 Hz, 3H). 13C NMR
Compound 6j: White solid, yield 40%. 1H NMR (400 MHz, CDCl3)
d 9.16 (s, 1H), 8.30 (d, J = 8.1 Hz, 1H), 7.75 (d, J = 8.1 Hz, 1H), 7.44–
7.27 (m, 7H), 6.74 (dt, J = 9.8, 5.0 Hz, 3H), 6.24 (br, 1H), 3.84 (s, 3H),
3.82 (s, 3H), 3.58 (s, 2H), 3.38 (s, 2H), 3.31 (m, 4H), 2.83 (m, 2H),
2.35 (m, 2H), 2.23 (m, 4H). 13C NMR (101 MHz, CDCl3) d 173.94,
173.02, 164.67, 150.26 (J = 35.4 Hz), 149.26, 148.86, 148.44,
137.15, 136.90, 132.65, 129.27, 128.45, 127.57, 127.25, 121.65,
121.18 (J = 275.7 Hz), 112.95, 111.61, 62.76, 58.57, 56.06, 55.92,
49.06, 43.01, 40.42, 39.16, 31.66. HRMS calcd for [M+H]+
628.2748, found 628.2742.
(101 MHz, DMSO)
d 173.78, 170.18, 166.51, 147.28, 138.53,
133.22, 132.53, 132.25, 131.87, 128.65, 128.21, 128.03, 127.78,
127.56, 127.32, 126.91, 126.72, 125.85, 125.47, 125.35, 124.12,
62.17, 57.53, 48.79, 39.90, 38.71, 38.33, 31.39, 27.98, 15.42. HRMS
calcd for [M+H]+ 577.3179, found 577.3195.
Compound 6e: White solid, yield 65%. 1H NMR (400 MHz,
DMSO-d6) d 8.62 (s, 1H), 8.55 (s, 2H), 8.32 (s, 1H), 8.01 (t,
J = 6.6 Hz, 2H), 7.95–7.82 (m, 2H), 7.79 (d, J = 8.1 Hz, 1H), 7.55–
7.45 (m, 2H), 7.44–7.37 (m, 1H), 7.37–7.28 (m, 5H), 7.26 (d,
J = 4.6 Hz, 1H), 3.82 (s, 2H), 3.46 (s, 2H), 3.12 (t, J = 8.6 Hz, 4H),
2.65 (m, 2H), 2.30 (m, 2H), 2.14 (m, 2H), 2.05 (m, 2H). 13C NMR
Compound 6k: White solid, yield 67%. 1H NMR (400 MHz, DMSO)
d 8.06 (br, 1H), 7.97 (d, J = 3.60 Hz, 1H), 7.87 (br, 1H), 7.77 (d,
J = 1.20 Hz, 1H), 7.74 (br, 1H), 7.31 (m, 4H), 7.24 (dd, J = 8.40,
5.7 Hz, 3H), 7.20–7.15 (m, 1H), 7.08 (t, J = 8.90 Hz, 2H), 3.43 (s,
2H), 3.10 (m, 4H), 2.59 (m, 2H), 2.23 (m, 2H), 2.11 (m, 2H), 1.95
(m, 2H). 13C NMR (101 MHz, DMSO) d 174.05, 170.73, 161.81,
161.47 (J = 242.40 Hz), 140.47, 139.10, 132.91 (J = 3.03 Hz),
131.46, 131.30 (J = 7.07 Hz), 129.76, 129.25, 128.65, 128.21,
127.37, 115.30 (J = 21.21 Hz), 62.69, 58.33, 49.33, 41.86, 39.33,
38.74, 31.96. HRMS calcd for [M+H]+ 523.2180, found 523.2169.
Compound 6l: White solid, yield 60%. 1H NMR (400 MHz, DMSO-
d6) d 9.20 (s, 1H), 8.83 (s, 1H), 8.49 (d, J = 7.7 Hz, 1H), 8.01 (d,
J = 7.8 Hz, 3H), 7.94–7.76 (m, 3H), 7.57–7.46 (m, 2H), 7.46–7.28
(m, 2H), 3.82 (s, 2H), 3.11 (m, 4H), 2.13 (d, J = 12.3 Hz, 2H), 1.99
(d, J = 12.5 Hz, 2H), 1.66 (m, 4H). 13C NMR (101 MHz, DMSO) d
173.24, 170.34, 163.98, 149.42, 147.78 (J = 34.34 Hz), 137.75,
133.33, 133.24, 132.49, 131.86, 128.25, 127.56, 126.96, 125.86,
125.50, 125.36, 124.06, 121.36 (J = 275.73 Hz), 120.14
(J = 2.02 Hz), 66.99, 39.76, 38.97, 38.38, 36.28, 24.15. HRMS calcd
for [M+H]+ 513.2114, found 513.2115.
(101 MHz, DMSO)
133.23, 132.46,
d
173.16, 170.26, 163.75, 138.52, 136.96,
131.85, 130.10 (J = 33.33 Hz), 128.66
(J = 14.14 Hz), 128.24, 128.07, 127.52, 126.95, 125.83, 125.48,
125.33, 125.10, 124.61, 124.03, 123.11 (J = 274.72 Hz), 120.07,
62.06, 58.32, 54.80, 48.78, 48.52, 38.35, 31.34. HRMS calcd for
[M+H]+ 685.2614, found 685.2616.
Compound 6f: White solid, yield 75%. 1H NMR (400 MHz, CDCl3)
d 7.95 (d, J = 8.3 Hz, 1H), 7.78 (d, J = 7.9 Hz, 1H), 7.75–7.69 (m, 1H),
7.54 (d, J = 3.0 Hz, 1H), 7.46 (tt, J = 14.7, 7.2 Hz, 4H), 7.38 (t,
J = 5.4 Hz, 2H), 7.36–7.27 (m, 5H), 7.11–6.98 (m, 2H), 6.43 (s, 1H),
3.92 (s, 2H), 3.51 (s, 2H), 3.31–3.16 (m, 4H), 2.72 (d, J = 11.6 Hz,
2H), 2.24 (m, 2H), 2.02 (m, 4H). 13C NMR (101 MHz, CDCl3) d
173.83, 172.06, 161.95, 138.55, 133.94, 132.19, 131.33, 130.74,
129.23, 129.16, 128.94, 128.72, 128.42, 128.15, 127.85, 127.53,
127.48, 126.61, 125.97, 125.72, 123.95, 62.74, 58.09, 49.02, 41.38,
39.97, 39.17, 31.79. HRMS calcd for [M+H]+ 555.2431, found
555.2430.
Compound 6m: White solid, yield 75%. 1H NMR (400 MHz,
CDCl3) d 9.06 (d, J = 1.3 Hz, 1H), 8.16 (dd, J = 8.1, 1.7 Hz, 1H),
7.96–7.88 (m, 1H), 7.88–7.81 (m, 1H), 7.80–7.71 (m, 1H), 7.65 (d,
J = 8.1 Hz, 1H), 7.55–7.45 (m, 2H), 7.45–7.34 (m, 2H), 6.99 (d,
J = 4.6 Hz, 1H), 6.45 (br, 1H), 6.28 (d, J = 5.5 Hz, 1H), 3.94 (s, 2H),
3.25 (dd, J = 11.7, 5.7 Hz, 4H), 2.00 (d, J = 13.5 Hz, 2H), 1.65 (t,
J = 11.8 Hz, 5H), 1.43–1.23 (m, 3H). 13C NMR (101 MHz, CDCl3) d
174.14, 172.48, 164.20, 150.35 (J = 35.35 Hz), 148.42, 136.79,
133.99, 132.73, 131.12, 131.02, 128.85, 128.48, 128.36, 126.73,
126.11, 125.70, 123.71, 121.14 (J = 275.75 Hz), 120.25
(J = 3.03 Hz), 60.45, 41.49, 40.78, 39.10, 31.93, 25.07, 21.65. HRMS
calcd for [M+H]+ 527.2271, found 527.2285.
Compound 6g: White solid, yield 75%. 1H NMR (400 MHz,
DMSO-d6) d 9.31 (s, 1H), 8.05 (d, J = 7.7 Hz, 1H), 7.98–7.83 (m,
3H), 7.84–7.76 (m, 1H), 7.59 (s, 1H), 7.56–7.47 (m, 2H), 7.46–
7.37 (m, 2H), 7.28 (tt, J = 14.1, 7.1 Hz, 5H), 7.07 (t, J = 7.7 Hz, 1H),
6.71 (d, J = 8.1 Hz, 2H), 6.67–6.58 (m, 1H), 3.85 (s, 2H), 3.42 (m,
4H), 3.10 (m, 4H), 2.47 (s, 2H), 2.05 (t, J = 10.6 Hz, 2H), 1.94–1.77
(m, 4H). 13C NMR (101 MHz, DMSO) d 174.23, 170.98, 170.88,
157.68, 139.10, 138.20, 133.78, 133.12, 132.46, 129.50, 129.16,
128.77, 128.61, 128.20, 127.48, 127.29, 126.43, 126.04, 125.94,
124.72, 120.24, 116.66, 113.79, 62.70, 57.65, 55.33, 48.90, 43.31,
40.32, 38.83, 31.73. HRMS calcd for [M+H]+ 579.2972, found
555.2964.
Compound 6n: White solid, yield 70%. 1H NMR (400 MHz,
DMSO-d6) d 8.92 (s, 1H), 8.57 (s, 2H), 8.30 (s, 1H), 7.99 (dd,
J = 6.3, 3.5 Hz, 2H), 7.94–7.83 (m, 2H), 7.80 (d, J = 8.1 Hz, 1H),
7.54–7.46 (m, 2H), 7.44–7.37 (m, 1H), 7.33 (d, J = 6.4 Hz,
1H), 3.80 (s, 2H), 3.10 (t, J = 6.7 Hz, 4H), 2.15 (dd, J = 12.6, 7.0 Hz,
2H), 1.99 (dd, J = 12.9, 4.8 Hz, 2H), 1.66 (d, J = 5.2 Hz, 4H). 13C
NMR (101 MHz, DMSO) d 173.33, 170.22, 163.64, 136.81, 133.23,
132.46, 131.84, 130.06 (J = 33.33 Hz), 128.60 (J = 4.04 Hz), 128.24,
127.51, 126.95, 125.82, 125.48, 125.33, 124.48, 124.02, 121.77,
67.05, 40.15, 39.77, 38.34, 36.35, 24.33. HRMS calcd for [M+H]+
580.2036, found 580.2035.
Compound 6h: White solid, yield 46%. 1H NMR (400 MHz, CDCl3)
d 9.14 (s, 1H), 8.27 (d, J = 7.8 Hz, 1H), 7.70 (d, J = 8.0 Hz, 1H), 7.32
(m, 7H), 7.20 (dd, J = 14.1, 7.4 Hz, 1H), 6.98–6.84 (m, 3H), 6.70
(m, 1H), 3.56 (s, 2H), 3.43 (s, 2H), 3.27 (m, 4H), 2.80 (d,
J = 11.0 Hz, 2H), 2.33 (m, 2H), 2.18 (m, 4H). 13C NMR (101 MHz,
CDCl3) d 173.87, 171.73, 164.66, 162.86 (J = 247.5 Hz), 150.42
(J = 38.4 Hz), 148.70, 137.28 (J = 7.1 Hz), 137.06, 132.47, 130.26
(J = 8.1 Hz), 130.05, 129.27, 128.47, 127.62, 125.06 (J = 3.3 Hz),
121.13 (J = 274.4 Hz), 120.31 (J = 2.2 Hz), 116.29 (J = 22.2 Hz),
114.12 (J = 21.2 Hz), 62.72, 58.47, 49.02, 43.07, 40.17, 39.26,
31.70. HRMS calcd for [M+H]+ 586.2442, found 586.2448.
Compound 6i: White solid, yield 55%. 1H NMR (400 MHz, CDCl3)
d 9.12 (s, 1H), 8.33–8.19 (m, 1H), 7.72 (d, J = 8.1 Hz, 1H), 7.31 (q,
4.1.2. General procedure for synthesis of compound 6o–6p
The synthetic procedure of compound 3i was conducted accord-
ing to the reported procedures.56,57 To a 100 mL round-bottomed