S. Mukherjee et al. / Bioorg. Med. Chem. 9 (2001) 337±345
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1
(100); H NMR (250 MHz, CDCl3): d 1.67 and 1.78
1-[2-Hydroxy-3-(3-methyl-2-butenyl)-4,5,6-trimethoxy-
phenyl]-3-(3,4,5-trimethoxyphenyl)propenone (17). The
compound 17 was puri®ed by ¯ash column chromato-
graphy using ethylacetate: n-hexane (3:17) as eluent as
an oil(895 mg) in 55.7% yiedl. Rf: 0.15 (ethylacetate:
n-hexane, 1:9); EIMS, m/z (% rel. int.): 472 [M]+(33),
263 (41), 223 (43), 197 (28), 181 (43), 149 (33), 97 (31),
83 (38), 69 (83), 57 (74), and 43 (100); 1H NMR
(250 MHz, CDCl3): d 1.67 and 1.77 (6H, 2s, 3H each, C-
400H, and C-500H), 3.33 (2H, d, J=7.0 Hz, C-100H), 3.83,
3.88, 3.91, 3.92, 3.93, and 3.96 (18H, 6s, 3H each,
6ÂOCH3), 5.19 (1H, t, J=7.0 Hz, C-200H), 6.84 (2H, s, C-
2H, and C-6H), 7.75 (1H, d, J=13.1 Hz, Ha), 7.76 (1H,
d, J=13.1 Hz, Hb), and 13.25 (1H, s, chelated OH); 13C
NMR (62.9 MHz, CDCl3): d 17.65 (C-500), 22.31 (C-100),
25.63 (C-400), 56.04, 56.13, 60.84, 61.01, and 62.02
(6ÂOCH3), 105.52 (C-2, and C-6), 106.58 (C-1), 111.20
(C-30), and 119.08 (C-10), 122.28 (C-200), 125.88 (C-a),
131.60 (C-300), 138.66 (C-50), 140.17 (C-4), 143.21 (C-b),
153.33 (C-20, C-3, and C-5), 158.32 and 158.88 (C-40 and
C-60), and 193.24 (CO); IR (KBr) nmax: 2937, 1692,
1583, 1504, 1463, 1418, 1325, 1128, 1045, and
(6H, 2s, C-400H and C-500H), 3.33 (2H, d, J=7.0 Hz, C-
100H), 3.84, 3.88, and 3.95 (9H, 3s, 3H each, 3ÂOCH3),
5.18 (1H, t, J=7.0 Hz, C-200H), 7.43±7.45 (3H, m, C-2H,
C-5H and C-6H), 7.67 (1H, d, J=15.8 Hz, Ha), 7.87
(1H, d, J=15.5 Hz, Hb), and 13.11 (1H, s, chelated
OH); 13C NMR (62.9 MHz, CDCl3): d 17.66 (C-500),
22.30 (C-100), 25.64 (C-400), 60.88, 61.02, and 61.96
(3ÂOCH3), 111.05 (C-30), 119.06 (C-10), 122.20 (C-200),
127.23 (C-a), 128.45, 129.59 and 130.79 (C-2, C-5, and C-
6), 131.69 (C-300), 133.13, 133.91, and 135.31 (C-1, C-3,
and C-4), 138.69 (C-50), 139.82 (C-b), 153.41 (C-20),
158.72 (C-60), 158.95 (C-40), and 192.99 (CO); IR (KBr)
n
max: 2927, 1633, 1603, 1565, 1469, 1405, 1335, 1276,
1200, 1143, 1112, 1096, 1049, and 979 cmÀ1
.
1-[2-Hydroxy-3-(3-methyl-2-butenyl)-4,5,6-trimethoxy-
phenyl]-3-(3,4-dimethoxyphenyl)propenone (15). The com-
pound was puri®ed by ¯ash column chromatography
using ethylacetate: n-hexane (1:4) as eluent to aord 15 as
a semi-solid (877mg) in 58.3% yield. Rf: 0.28 (ethylace-
tate: n-hexane, 1:4); EIMS, m/z (% rel. int.): 442 [M]+
(26), 441 (100), 426 (17), 398 (13), 277 (15), 262 (64), 235
1005 cmÀ1
.
1
(16), 223 (48), 149 (20), 131 (14), and 69 (49); H NMR
(300 MHz, CDCl3): d 1.70, and 1.80 (6H, 2s, 3H each,
C-400H, and C-500H), 3.36 (2H, d, J=6.3 Hz, C-100H),
3.86, 3.91, and 3.95 (15H, 3s, 5ÂOCH3), 5.22 (1H, t,
J=6.3 Hz, C-200H), 6.92 (1H, d, J=8.1 Hz, C-5H),
7.05±7.24 (2H, m, C-2H, and C-6H), 7.81 (2H, s, Ha, and
Hb) and 13.32 (1H, s, chelated OH); 13C NMR (75.5MHz,
CDCl3): d 17.81 (C-500), 22.51 (C-100), 25.78 (C-400), 55.97,
60.96, 61.14, 61.58, and 62.09 (5ÂOCH3), 109.41 (C-10),
110.51, and 111.32 (C-2, and C-5), 118.54 and 119.32 (C-1
and C-30), 122.60 (C-a), 123.00 (C-200), 124.67 (C-6), 129.17
(C-300), 141.65 (C-50), 143.58 (C-b), 149.34 (C-3), 151.42
(C-4), 153.48 (C-20), 156.55 (C-60), 158.31 (C-40), and
193.45 (CO); IR (KBr) nmax: 2931, 2852, 1626, 1556,
1-[2-Hydroxy-3-(3-methyl-2-butenyl)-4,5,6-trimethoxy-
phenyl] - 3 - (3,4 - methylenedioxyphenyl)propenone (18).
The crude product was ¯ash column chromatographed
using chloroform:n-hexane (9:11) as eluent to aord the
desired compound as a yellowish-orange solid (997 mg)
in 68.8% yield; mp 64±65 ꢀC. Rf: 0.15 (chloroform:
n-hexane, 2:3); EIMS, m/z (% rel. int.): 426 [M]+(54),
411 (27), 383 (21), 371 (14), 278 (8), 263 (100), 235 (35),
223 (53), 205 (21), 195 (8), 175 (24), 148 (38), 135 (29)
117 (26), 89 (47), and 77 (18); 1H NMR (300 MHz,
CDCl3): d 1.68 and 1.79 (6H, 2s, 3H each, C-400H and
C-500H), 3.35 (2H, d, J=6.9 Hz, C-100H), 3.85, 3.89, and
3.95 (9H, 3s, 3H each, 3ÂOCH3), 5.23 (1H, t, J=6.9 Hz,
C-200H), 6.02 (2H, s, OCH2O), 6.85 (1H, d, J=7.9 Hz,
C-5H), 7.13 (1H, dd, J=1.4 and 8.0 Hz, C-6H), 7.15
(1H, d, J=1.0 Hz, C-2H), 7.76 (2H, s, Ha and Hb) and
13.28 (1H, s, chelated OH); 13C NMR (75.5 MHz,
CDCl3): d 17.81(C-500), 22.50 (C-100), 25.78 (C-400), 60.99,
61.14, and 62.05 (3ÂOCH3), 101.61 (OCH2O), 106.68
(C-2), 108.69 (C-5), 111.44 (C-30), 122.58 (C-10), 123.23
(C-200), 124.90, and 125.19 (C-a and C-6), 129.43 (C-1),
131.63 (C-300), 138.84 (C-50), 143.23 (C-b), 148.45 and
149.80 (C-3 and C-4), 153.55 (C-20), 158.35 (C-60),
159.01 (C-40), 193.45 (CO); IR (KBr) nmax: 2933, 2361,
1512, 1463, 1343, 1265, 1139, and 1046 cmÀ1
.
1-[2-Hydroxy-3-(3-methyl-2-butenyl)-4,5,6-trimethoxy-
phenyl]-3-(2,5-dimethoxyphenyl)propenone (16). The
crude product was ¯ash column chromatographed using
ethylacetate: n-hexane (1:9) as eluent to yield the desired
compound as an oil(912 mg) in 60.6% yiedl. Rf: 0.15
(ethylacetate: n-hexane, 1:9); EIMS, m/z (% rel. int.):
442 [M]+ (64), 428 (29), 412 (30), 400 (25), 388 (32), 279
(35), 263 (79), 235 (38), 223 (100), 200 (30), 191 (30), 149
1
(55), and 95 (27); H NMR (300 MHz, CDCl3): d 1.69,
and 1.79 (6H, 2s, 3H each, C-400H, and C-500H), 3.35
(2H, d, J=7.1 Hz, C-100H), 3.81, 3.83, 3.84 and 3.95
(15H, 4s, 5ÂOCH3), 5.22 (1H, t, J=7.1 Hz, C-200H),
6.86±6.95 (2H, m, C-3H, and C-4H), 7.19 (1H, d,
J=2.8 Hz, C-6H), 7.95 (1H, d, J=15.8 Hz, Ha), 8.11
(1H, d, J=15.7 Hz, Hb), and 13.30 (1H, s, chelated
OH); 13C NMR (75.5 MHz, CDCl3): d 17.77 (C-500),
22.47 (C-100), 25.74 (C-400), 55.84, 56.16, 60.98, 61.11,
and 62.04 (5ÂOCH3), 111.00, 112.59, and 113.70 (C-3,
C-30 and C-4), 117.00 (C-6), 119.10 (C-10), 122.66 (C-1),
124.50 (C-a), 127.56 (C-200), 131.65 (C-300), 138.41 (C-û),
139.00 (C-50), 153.00, and 153.68 (C-2, C-20 and C-5),
158.00 (C-60), 159.08 (C-40), and 194.09 (CO); IR
(KBr) nmax: 3421, 2937, 2361, 1692, 1627, 1583, 1503,
1627, 1557, 1447, 1255, 1146, 1043, and 982 cmÀ1
.
1-[2-Hydroxy-3-(3-methyl-2-butenyl)-4,5,6-trimethoxy-
phenyl]-3-(2-furanyl)propenone (19). The crude product
was ¯ash column chromatographed using chloroform:n-
hexane (3:7) as eluent to aord the compound 19 as an
oil(716 mg) in 56.6% yiedl.
Rf: 0.26 (chloroform:n-
hexane, 3:7); EIMS, m/z (% rel. int.): 372 [M]+ (22),
371 (100), 356 (29), 328 (21), 316 (33), 263 (77), 235 (25),
1
223 (73), 205 (12), 177 (12), 121 (22), and 65 (16); H
NMR (300 MHz, CDCl3): d 1.68 and 1.79 (6H, 2s, 3H
each, C-400H and C-500H), 3.34 (2H, d, J=6.9 Hz, C-
100H), 3.83, 3.92, and 3.95 (9H, 3s, 3ÂOCH3), 5.21 (1H, t,
J=6.9Hz, C-200H), 6.51 (1H, dd, J=1.6 and 3.1 Hz, C-
4H), 6.70 (1H, d, J=3.1 Hz, C-3H), 7.52 (1H, s, C-5H),
1463, 1418, 1325, 1128, and 1046 cmÀ1
.