SYNTHESIS OF MODIFIED PSORALEN ANALOGUES
299
81%; mp 199–200°C; UV, EtOH, λmax, nm (logε ): 203 (logε ): 202 (4.82), 240 (4.66), 250 (4.68), 304 (4.43);
IR (cm–1): 3049, 1741, 1705, 1655, 1614, 1587, 1564,
(4.54), 213 (4.47), 226 (4.39), 250 (4.37), 301 (4.18),
and 331 (3.97); IR (cm–1): 3105, 1756, 1704, 1669, 1512, 1363, 1300, 1255, 1184, 1170, 1136, 1110, 1028,
1627, 1575, 1510, 1387, 1349, 1312, 1298, 1166, 1085, 820. Found, %: C 70.29; H 5.07. C23H20O6. Calculated,
854. Found, %: C 68.66; H 4.19. C21H15FO5. Calcu-
lated, %: C 68.85, H 4.13.
3-{3'-(4'-Fluorophenyl)-5',9'-dimethyl-7'-oxofuro-
[3,2-g]chromen-6'-yl}propanoic acid (XXXVII):
yield 92%; mp 263–265°C; UV, EtOH, λmax, nm
%: C 70.40, H 5.14.
3-{3'-(3'-Methoxyphenyl)-5'-methyl-7'-oxofuro-
[3,2-g]chromen-6'-yl}propanoic acid (XLIV): yield
87%; mp 200–201°C; UV, MeCN, λmax, nm (logε ):
213 (4.61), 251 (4.40), 298 (4.24), and 328 (3.92); IR
(cm–1): 2940, 1719, 1670, 1627, 1613, 1578, 1418,
1397, 1354, 1310, 1211, 1158, 1095, 857. Found, %: C
69.74; H 4.82. C22H18O6. Calculated, %: C 69.83, H
4.79.
(logε ): 204 (4.55), 215 (4.51), 227 (4.41), 250 (4.42),
304 (4.23), and 342 (3.87); IR (cm–1): 3100, 1753,
1705, 1669, 1612, 1588, 1570, 1510, 1388, 1347, 1314,
1298, 1236, 1168, 1134, 1107, 852. Found, %: C 69.32,
H 4.59. C22H17FO5. Calculated, %: C 69.47, H 4.50.
3-{3'-(3'-Methoxyphenyl)-5',9'-dimethyl-7'-oxo-
furo[3,2-g]chromen-6'-yl}propanoic acid (XLV):
yield 79%; mp 234–235°C; UV, EtOH, λmax, nm
3-{3'-(4'-Chlorophenyl)-5'-methyl-7'-oxofuro[3,2-
g]chromen-6'-yl}propanoic acid (XXXVIII): yield
91%; mp 207–208°C; UV, MeCN, λmax, nm (logε ):
204 (4.71), 248 (4.59), 301 (4.34), and 335 (4.02).; IR
(cm–1): 3091, 1739, 1714, 1681, 1629, 1582, 1491,
1394, 1272, 1160, 1115, 1096, 832. Found, %: C 65.68;
H 4.07. C21H15ClO5. Calculated, %: C 65.89, H 3.95.
(logε): 214 (4.49), 251 (4.23), and 304 (4.11); IR (cm–1):
2961, 1701, 1612, 1595, 1570, 1428, 1387, 1356, 1329,
1295, 1279, 1209, 1123, 1104, 1035. Found, %: C
70.24; H 5.21. C23H20O6. Calculated, %: C 70.40, H
5.14.
3-{4'-Methyl-2'-oxo-6',7',8',9'-tetrahydrobenzo-
[4,5]furo[3,2-g]chromen-3'-yl}propanoic acid (XLVI):
yield 85%; mp 247–248°C; UV, EtOH, λmax, nm
3-{3'-(4'-Chlorophenyl)-5',9'-dimethyl-7'-oxofuro-
[3,2-g]chromen-6'-yl}propanoic acid (XXXIX):
yield 88%; mp 269–270°C; UV, EtOH, λmax, nm
(logε ): 211 (4.23), 255 (4.22), 298 (3.94), and 338
(logε ): 207 (4.44), 216 (4.40), 250 (4.39), and 302
(3.80); IR (cm–1): 3240, 2937, 1739, 1672, 1626, 1576,
1468, 1402, 1294, 1269, 1185, 1170, 1154, 1118, 863;
1H NMR: 1.85 (2 H, m, H7'), 1.92 (2 H, m, H8'), 2.40
(2 H, t, J 7.2, H2), 2.50 (3 H, s, 4'-CH3), 2.64 (2 H, m,
H6'), 2.73 (2 H, m, H9'), 2.81 (2 H, t, J 7.2, H3), 7.40
(1 H, s, H11'), 7.73 (1 H, s, H5'), 12.05 (1 H, br. s,
COOH). Found, %: C 70.09; H 5.67. C19H18O5. Calcu-
lated, %: C 69.93, H 5.56.
(4.19); IR (cm–1): 3095, 1743, 1715, 1675, 1589, 1495,
1379, 1367, 1298, 1166, 1134, 1110, 842. Found, %: C
66.48, H 4.27. C22H17ClO5. Calculated, %: C 66.59, H
4.32.
3-{3'-(4'-Bromophenyl)-5'-methyl-7'-oxofuro[3,2-
g]chromen-6'-yl}propanoic acid (XL): yield 92%;
mp 224–225°C; UV, MeCN, λmax, nm (logε ): 202
(4.58), 248 (4.46), 295 (4.24), and 340 (3.81); IR (cm–1):
3091, 1739, 1713, 1679, 1629, 1581, 1394, 1272, 1160,
1115, 1093, 1073, 873, 829. Found, %: C 59.18; H
3.57. C21H15BrO5. Calculated, %: C 59.04, H 3.54.
3-{4',11'-Dimethyl-2'-oxo-6',7',8',9'-tetrahydro-
benzo[4,5]furo[3,2-g]chromen-3'-yl}propanoic acid
(XLVII): yield 81%; mp 245–246°C; UV, EtOH, λmax
,
nm (logε ): 211 (4.47), 256 (4.46), 302 (4.13), 340
3-{3'-(4'-Bromophenyl)-5',9'-dimethyl-7'-oxofuro-
(3.84); IR (cm–1): 3387, 2944, 1730, 1703, 1681, 1639,
1591, 1442, 1412, 1339, 1275, 1188, 1142, 1094, 908,
783; 1H NMR: 1.84 (2 H, m, H7'), 1.91 (2 H, m, H8'),
2.39 (2 H, t, J 7.2, H2), 2.45 (3 H, s, C11'-CH3), 2.50
(3 H, s, C4'-CH3), 2.62 (2 H, m, H6'), 2.74 (2 H, m,
H9'), 2.80 (2 H, t, J 7.2, H3), 7.55 (1 H, s, H5'), 12.00
(1 H, br. s, COOH). Found, %: C 70.49; H 5.97.
C20H20O5. Calculated, %: C 70.57, H 5.92.
[3,2-g]chromen-6'-yl}propanoic acid (XLI): yield
94%; mp 277–278°C; UV, EtOH, λmax, nm (logε ): 206
(4.58), 217 (4.49), 251 (4.50), and 302 (4.28); IR (cm–1):
3093, 1739, 1711, 1675, 1589, 1491, 1378, 1368, 1341,
1297, 1164, 1133, 1112, 1079, 841. Found, %: C 59.68;
H 3.87. C22H17BrO5. Calculated, %: C 59.88, H 3.88.
3-{3'-(4'-Methoxyphenyl)-5'-methyl-7'-oxofuro-
[3,2-g]chromen-6'-yl}propanoic acid (XLII): yield
94%; mp 233–234°C; UV, EtOH, λmax, nm (logε ): 205
(4.57), 231 (4.40), 251 (4.39), 308 (4.16); IR (cm–1):
3044, 1730, 1701, 1679, 1627, 1587, 1577, 1511, 1396,
1303, 1278, 1255, 1183, 1161, 1113, 1085, 1028.
Found, %: C 69.69; H 4.87. C22H18O6. Calculated, %:
C 69.83, H 4.79.
ACKNOWLEDGMENTS
This work was supported by OAO Eksimed (Kyiv,
Ukraine).
REFERENCES
3-{3'-(4'-Methoxyphenyl)-5',9'-dimethyl-7'-oxo-
furo[3,2-g]chromen-6'-yl}propanoic acid (XLIII):
yield 86%; mp 254–255°C; UV, EtOH, λmax, nm
1. Golovkin, B.N., Rudenskaya, R.N., Trofimova, I.A., and
Shreter, A.I., Biologicheski aktivnye veshchestva rasti-
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY Vol. 30 No. 3 2004