Cao et al.
HRMS (ESI) m/z calcd for C23H34N2O2S [M + H]+
403.2420, found 403.2412.
145.11, 142.30, 141.05, 137.14, 135.18, 134.89, 132.60,
123.13, 52.00, 42.33, 38.08, 37.35, 31.41, 29.71, 29.14,
28.84, 27.48, 23.97, 22.18, 13.61, 12.40. HRMS (ESI) m/z
calcd for
417.2178.
1-((5-isopropyl-3,8-dimethylazulen-1-yl)sulfonyl)-4-(4-
methylbenzyl)piperazine (A12). 57.7% yield; purple
solid; m.p. 47–48 °C; IR (KBr): 2959, 2921, 2855, 1516,
1453, 1369, 1292, 1205, 1146, 1059, 923, 819, 725; 1H
NMR(400 MHz, CDCl3) d(ppm): 8.26 (d, J = 2.0 Hz, 1H),
8.12 (s, 1H), 7.58 (d, J = 10.8 Hz, 1H), 7.38 (d,
J = 11.2 Hz, 1H), 7.17 (d, J = 8.0 Hz, 2H), 7.10 (d,
J = 8.0 Hz, 2H), 3.46 (s, 2H), 3.41–3.35 (m, 4H), 3.34 (s,
3H), 3.14 (dd, J = 13.6, 6.8 Hz, 1H), 2.57 (s, 3H), 2.32 (s,
3H), 1.37 (d, J = 6.8 Hz, 6H); HRMS (ESI) m/z calcd for
C27H34N2O2S [M + H]+ 451.2420, found m/z 450.2413.
C
23H32N2O3S [M + H]+ 417.2213, found
3-(4-((5-isopropyl-3,8-dimethylazulen-1-yl)sulfonyl)pi-
perazin-1-yl)-1-(p-tolyl)ethan-1-one(B2). 36.4% yield;
purple solid; m.p. 65–66 °C; IR (KBr): 2957, 2924, 2861,
1679, 1606, 1457, 1374, 1288, 1204, 1145, 982, 923,
642, 600;1H NMR (400 MHz, CDCl3)
d
8.27 (d,
J = 2.0 Hz, 1H), 8.12 (s, 1H), 7.93 (d, J = 8.8 Hz, 2H),
7.59 (d, J = 9.6 Hz, 1H), 7.39 (d, J = 11.2 Hz, 1H), 6.94
(s, 1H), 6.92 (s, 1H), 3.64 (m, 4H), 3.38–3.33 (m, 8H),
3.30 (s, 3H), 3.11 (dd, J = 13.6, 6.8 Hz, 1H), 2.58 (m,
3H), 2.34 (s, 3H), 1.39 (d, J = 6.8 Hz, 6H); 13C NMR
(101 MHz, CDCl3) d 149.23, 144.95, 142.86, 141.10,
139.71, 137.30, 135.44, 135.13, 132.64, 130.91, 129.46,
128.93, 128.52, 127.30, 125.94, 123.35, 78.47, 52.66,
44.87, 44.55, 37.85, 36.09, 28.13, 24.62, 12.95. HRMS
(ESI) m/z calcd for C29H36N2O3S [M + H]+ 493.2526,
found 493.2552.
1-(2-chlorobenzyl)-4-((5-isopropyl-3,8-dimethylazulen-
1-yl)sulfonyl)piperazine (A13). 51.5% yield; purple oil;
IR (KBr): 2959, 2330, 1521, 1444, 1394, 1295, 1147, 923,
754; 1H NMR(400 MHz, CDCl3) d(ppm): 8.27 (d,
J = 2.0 Hz, 1H), 8.13 (s, 1H), 7.58 (d, J = 10.8 Hz, 1H),
7.45 (m, 1H), 7.33 (d, J = 8.0 Hz, 2H), 7.25–7.16 (m, 2H),
3.62 (s, 2H), 3.41–3.34 (m, 8H), 3.31 (s, 3H), 3.14 (dd,
J = 13.6, 6.8 Hz, 1H), 2.58 (s, 3H), 1.38 (d, J = 7.2 Hz,
6H); HRMS (ESI) m/z calcd for C26H31ClN2O2S [M + H]+
471.1874, found 471.1864.
1-(4-chlorophenyl)-3-(4-((5-isopropyl-3,8-dimethylazu-
len-1-yl)sulfonyl)piperazin-1-yl)ethan-1-one (B3). 32.6%
yield; purple solid; m.p. 69–70 °C; IR (KBr): 2960, 2925,
16821589, 1459, 1371, 1295, 1147, 1091, 1062, 928,
639; 1H NMR (400 MHz, CDCl3) d(ppm): 8.29 (d,
J = 2.0 Hz, 1H), 8.12 (s, 1H), 7.98–7.95 (m, 2H), 7.60 (d,
J = 11.2 Hz, 1H), 7,40 (d, J = 11.2 Hz, 1H), 7.14 (s, 1H),
7.11 (s, 1H), 3.65 (m, 4H), 3.39–3.34 (m, 8H), 3.29 (s,
3H), 3.14 (dd, J = 8.2, 4.8 Hz, 1H), 2.57 (s, 3H), 1.39 (d,
1-((5-isopropyl-3,8-dimethylazulen-1-yl)sulfonyl)-4-
propylpiperazine (A14). 44.6% yield; purple solid; m.p.
72–73 °C; IR (KBr): 2961, 2867, 2807, 1541, 1463, 1370,
1
1292, 1149, 1059, 985, 934, 828, 722; HNMR(400 MHz,
CDCl3) d(ppm): 8.27 (d, J = 2.0 Hz, 1H), 8.12 (s, 1H), 7.58
(d, J = 11.2 Hz, 1H), 7.38 (d, J = 11.2 Hz, 1H), 3.48
(t, J = 3.6 Hz, 2H), 3.40–3.35 (m, 8H), 3.34 (s, 3H), 3.14
(dd, J = 13.6, 6.8 Hz, 1H), 2.57 (s, 3H), 1.48 (m, 2H),
1.38 (d, J = 6.8 Hz, 6H), 0.90 (t, J = 3.2 Hz, 3H); HRMS
(ESI) m/z calcd for C22H32N2O2S[M + H]+ 389.2263, found
389.2263.
J = 6.8 Hz,
6H);
HRMS
(ESI)
m/z
calcd
for
C28H33ClN2O3S [M+H]+ 513.1979, found 513.2012.
3-(4-((5-isopropyl-3,8-dimethylazulen-1-yl)sulfonyl)pipe-
razin-1-yl)-1-(4-methoxyphenyl)ethan-1-one (B4). 35.7%
yield; purple solid; m.p. 61–62 °C; IR (KBr): 2958, 2926,
2859, 1674, 1599, 1460, 1373, 1293, 1260, 1146, 1028,
926, 642, 598; 1H NMR (400 MHz, CDCl3) d(ppm): 8.28
(d, J = 2.0 Hz, 1H), 8.13 (s, 1H), 7.84 (d, J = 11.2 Hz,
2H), 7.60 (d, J = 11.2 Hz, 1H), 7.40 (d, J = 11.2 Hz, 1H),
7.27 (s, 1H), 7.24 (s, 1H), 3.65 (m, 4H), 3.48 (s, 3H), 3.47-
3.43 (m, 8H), 3.31 (s, 3H), 3.12 (dd, J = 13.6, 6.8 Hz,
1H), 2.57 (s, 3H), 1.38 (d, J = 6.8 Hz, 6H); HRMS (ESI) m/
1-ethyl-4-((5-isopropyl-3,8-dimethylazulen-1-yl)sulfonyl)
piperazine (A15). 46.2% yield; purple solid; m.p. 62–
64 °C; IR (KBr): 2963, 1457, 1380, 1292, 1144, 911, 725,
635; 1HNMR(400 MHz, CDCl3) d(ppm): 8.19 (d,
J = 2.0 Hz, 1H), 8.05 (s, 1H), 7.50 (d, J = 10.8 Hz, 1H),
7.30 (d, J = 10.8 Hz, 1H), 3.48 (q, J = 3.6 Hz, 2H), 3.37–
3.23 (m, 11H), 3.05 (dd, J = 13.6, 6.8 Hz, 1H), 2.50 (s,
3H), 1.29 (d, J = 6.8 Hz, 6H), 0.98 (t, J = 3.2 Hz, 3H);
HRMS (ESI) m/z calcd for C21H30N2O2S [M + H]+
375.2107, found 375.2114.
z
calcd for C29H36N2O4S [M + H]+ 509.2475, found
509.2491.
(3-(4-((5-isopropyl-3,8-dimethylazulen-1-yl)sulfonyl)
piperazin-1-yl)-1-phenylethan-1-one (B5). 58.3% yield;
purple solid; m.p. 65–66 °C; IR (KBr): 2958, 16781452,
4-(4-((5-isopropyl-3,8-dimethylazulen-1-yl)sulfonyl)
piperazin-1-yl)propan-2-one (B1). 39.0% yield; purple
solid; m.p. 57–58 °C; IR (KBr): 2960, 2927, 1716, 1459,
1371, 1297, 1148, 924, 642,598; 1H NMR (400 MHz,
CDCl3) d(ppm): 8.29 (d, J = 2.0 Hz, 1H), 8.10 (s, 1H), 7.63
(d, J = 11.2 Hz, 1H), 7.40 (d, J = 11.2 Hz, 1H), 3.65 (m,
4H), 3.38–3.32 (m, 8H), 3.24 (s, 3H), 3.14 (dd, J = 10.8,
6.0 Hz, 1H), 2.56 (s, 3H), 2.23 (s, 3H), 1.40 (d,
J = 6.8 Hz, 6H); 13C NMR (101 MHz, DCCl3) d 148.76,
1
1374, 1287, 1146, 924, 638; H NMR (400 MHz, CDCl3) d
(ppm): 8.28 (d, J = 2.0 Hz, 1H), 8.13 (s, 1H), 7.93 (d,
J = 11.2 Hz, 2H), 7.57 (m, 2H), 7.56 (d, J = 11.2 Hz, 1H),
7.45 (d, J = 11.2 Hz, 1H), 7.26 (d, J = 11.2 Hz, 1H), 3.64
(m, 4H), 3.39–3.34 (m, 8H), 3.31 (s, 3H), 3.12 (dd,
J = 13.6, 6.8 Hz, 1H), 2.57 (s, 3H), 1.38 (d, J = 6.8 Hz,
6H); 13C NMR (101 MHz, CDCl3) d 149.25, 144.87,
4
Chem Biol Drug Des 2016