556
D.J. Prasad et al. / European Journal of Medicinal Chemistry 44 (2009) 551e557
(Mþ, 65), 235 (48), 163 (53); 13C NMR (CDCl3, d): 14.58
(CH2), 28.17 (SCH3), 137 (C3), 141 (C6), 145 (C8), 115e
128 (aromatic carbons of 4-methylthiophenyl), 135e142
(aromatic carbons of 4-flurophenyl).
7.62 (d, 2H, J ¼ 8 Hz, 4-methylthiophenyl), 7.55 (d, 2H,
J ¼ 8.1 Hz, 4-chlorophenyl), 8.95 (d, 2H, J ¼ 8.1 Hz, 4-chloro-
phenyl); FAB MS (m/z, %): 438 (Mþ þ 1, 100), 437 (Mþ, 47),
440 (M þ 2, 49), 380 (61), 298 (38); 13C NMR (CDCl3, d):
15.33 (CH2), 29.69 (SCH3), 133 (C3), 136 (C6), 144 (C8), 109e
121 (aromatic carbons of 4-methylthiophenyl), 122e127
(carbons of furan ring), 132e155 (aromatic carbons of 4-
chlorophenyl).
6.4.11. Compound 7a
IR (KBr, cmꢁ1): 3057 (Ar-H), 2912 and 2818 (CeH), 1596
and 1491 (C]N, C]C), 892, 875 and 840 (CeCl); 1H NMR
(CDCl3, d): 2.43 (s, 3H, SCH3), 4.49 (s, 2H, eCH2), 7.57 (d,
1H, J ¼ 3.8 Hz, furan-H), 7.82 (d, 1H, J ¼ 3.8 Hz, furan-H),
8.20 (s, 1H, 2,4,5-trichlorophenyl), 8.07 (s, 1H, 2,4,5-
trichlorophenyl), 7.12 and 7.25 (2d, 4H, J ¼ 8 Hz, 4-methyl-
thiophrenyl); FAB MS (m/z, %): 507 (Mþ þ 1, 100), 506
(Mþ), 508 (M þ 2, 72), 510 (M þ 4, 83), 512 (M þ 6, 75),
307 (73), 289 (48); 13C NMR (CDCl3, d): 16.32 (CH2),
30.43 (SCH3), 139.61 (C3), 147.43 (C6), 152.12 (C8), 121e
129 (aromatic carbons of 4-methylthiophenyl), 126e133
(carbons of furan ring), 132e147 (aromatic carbons of 2,4,5-
trichlorophenyl).
6.4.15. Compound 7e
IR (KBr, cmꢁ1): 3048 (Ar-H), 2896 (CeH), 1602, 1592,
1496 and 1470 (C]N, C]C), 763 (CeCl); 1H NMR
(CDCl3, d): 2.42 (s, 3H, SCH3), 4.44 (s, 2H, eCH2), 7.07
(d, 1H, J ¼ 3.6 Hz, furan-H), 7.30 (d, 1H, J ¼ 3.6 Hz, furan-
H), 7.21 (d, 2H, J ¼ 8 Hz, 4-methylthiophenyl), 7.34 (d, 2H,
J ¼ 8 Hz, 4-methylthiophenyl), 7.91 (d, 2H, J ¼ 8.8 Hz, 4-
nitrophenyl), 8.32 (d, 2H, J ¼ 8.8 Hz, 4-nitrophenyl); FAB
MS (m/z, %): 450 (Mþ þ 1, 100), 449 (Mþ, 57), 391 (47),
307 (36), 289 (21); 13C NMR (CDCl3, d): 15.39 (CH2),
30.08 (SCH3), 136 (C3), 139 (C6), 143 (C8), 116e128 (aro-
matic carbons of 4-methylthiophenyl), 127e132 (carbons of
furan ring), 129e165 (aromatic carbons of 4-nitrophenyl).
6.4.12. Compound 7b
IR (KBr, cmꢁ1): 3068 (Ar-H), 2917 and 2849 (CeH), 1592
and 1493 (C]N, C]C), 1535, 1348 (NO2 asymmetric and
symmetric stretching frequencies), 898, 879 (CeCl); 1H
NMR (CDCl3, d): 2.45 (s, 3H, SCH3), 4.41 (s, 2H, eCH2),
6.85 (d, 1H, J ¼ 4 Hz, furan-H), 7.23 (d, 1H, J ¼ 4 Hz,
furan-H), 7.13 (d, 2H, J ¼ 8 Hz, 4-methylthiophenyl), 7.34
(d, 2H, J ¼ 8 Hz, 4-methylthiophenyl), 7.82 (d, 1H,
J ¼ 2 Hz, 2-nitro-4-chlorophenyl), 7.73 (d, 1H, J ¼ 8.4 Hz,
2-nitro-4-chlorophenyl), 7.67 (d, 1H, J ¼ 2 Hz, 2-nitro-4-
chlorophenyl); FAB MS (m/z, %): 484 (Mþ þ 1, 100), 483
(Mþ), 485 (M þ 2, 47), 487 (29), 307 (15), 279 (21), 250
(18); 13C NMR (CDCl3, d): 14.96 (CH2), 30.83 (SCH3), 132
(C3), 141 (C6), 148 (C8), 117.17e126.32 (aromatic carbons
of 4-methylthiophenyl), 119e131 (carbons of furan ring),
137e159 (aromatic carbons of 2-nitro-4-chlorophenyl).
6.4.16. Compound 7f
IR (KBr, cmꢁ1): 3061 (Ar-H), 2892 (CeH), 1612, 1589 and
1468 (C]N, C]C), 1542 and 1361 (NO2 asym. and sym.);
1H NMR (CDCl3, d): 2.41 (s, 3H, SCH3), 4.39 (s, 2H, e
CH2), 6.65 (d, 2H, J ¼ 3.6 Hz, furan-H), 6.73 (2d, 2H,
J ¼ 3.6 Hz, furan-H), 7.28 (d, 2H, J ¼ 8 Hz, 4-methylthio-
phenyl), 7.31 (d, 2H, J ¼ 8 Hz, 4-methylthiophenyl), 7.51 (d,
2H, J ¼ 8.2 Hz, 4-bromophenyl), 7.55 (d, 2H, J ¼ 8.2 Hz, 4-
bromophenyl); FAB MS (m/z, %): 483 (Mþ, 91), 485
(M þ 2, 49), 350 (22), 248 (38), 157 (13); 13C NMR
(CDCl3, d): 15.33 (CH2), 30.21 (SCH3), 133 (C3), 137 (C6),
149 (C8), 110e126 (aromatic carbons of 4-methylthiophenyl),
127e135 (carbons of furan ring), 132e152 (aromatic carbons
of 4-nitrophenyl).
6.4.13. Compound 7c
IR (KBr, cmꢁ1): 3033 (Ar-H), 2917, 2848 (CeH), 1596,
1577, 1493 and 1478 (C]N, C]C), 1074, 1031 (CeF of
6.4.17. Compound 7g
IR (KBr, cmꢁ1): 3076 (Ar-H), 2845 (CeH), 1615, 1566 and
1
CF3); H NMR (CDCl3, d): 2.45 (s, 3H, SCH3), 4.42 (s, 2H,
1
1481 (C]N, C]C), 873 and 844 (CeCl); H NMR (CDCl3,
eCH2), 6.89 (d, 1H, J ¼ 3.6 Hz, furan-H), 7.26 (d, 1H,
J ¼ 3.6 Hz, furan-H), 7.21 (d, 1H, J ¼ 8.4 Hz, 4-methylthio-
phenyl), 7.35 (d, 1H, J ¼ 8.4 Hz, 4-methylthiophenyl), 7.53e
7.83 (m, 4H, 2-trifluoromethylphenyl); FAB MS (m/z, %):
473 (Mþ þ 1, 100), 472 (Mþ, 48), 431 (47), 391 (53), 307
(47); 13C NMR (CDCl3, d): 14.77 (CH2), 29.75 (SCH3), 143
(C3), 153 (C6), 155 (C8), 113.17e126.54 (aromatic carbons
of 4-methylthiophenyl), 132e138 (aromatic carbons of 2-
trifluromethylphenyl), 127e130 (carbons of furan ring).
d): 2.46 (s, 3H, SCH3), 4.36 (s, 2H, eCH2), 6.91 and 7.18 (2d,
2H, J ¼ 3.6 Hz, furan-H), 7.23 and 7.46 (2d, 4H, J ¼ 8.2 Hz, 4-
methylthiophenyl), 7.57 (dd, 1H, 2,5-dichlorophenyl), 7.62 and
7.88 (2d, 2H, J ¼ 8.2 Hz, 2,5-dichlorophenyl); FAB MS (m/z,
%): 473 (Mþ þ 1, 100), 472 (Mþ, 79), 474 (M þ 2, 64), 476
(M þ 4, 26), 365 (33), 237 (17); 13C NMR (CDCl3, d): 15.18
(CH2), 29.32 (SCH3), 135 (C3), 143 (C6), 155 (C8), 115e128 (ar-
omaticcarbonsof4-methylthiophenyl), 128e136(carbonsoffu-
ran ring), 131e158 (aromatic carbons of 4-nitrophenyl).
6.4.14. Compound 7d
IR (KBr, cmꢁ1): 3041 (Ar-H), 2892 (CeH), 1590, 1570, 1493
and 1478 (C]N, C]C), 1276, 1093 (CeO), 897 and 829 (Ce
References
[1] N.D. Heindel, I.R. Reid, J. Heterocycl. Chem. 17 (1980) 1087.
[2] B.S. Holla, B. Kalluraya, K.R. Sridhar, E. Drake, L.M. Thomas,
K.K. Bhandary, M.S. Levine, Eur. J. Med. Chem. 29 (1994) 301.
[3] The Merk Index, 12th ed. Merk and Co. Inc., Whitehouse Station, 1996.
1
Cl); H NMR (CDCl3, d): 2.43 (s, 3H, SCH3), 4.41 (s, 2H, e
CH2), 7.35 (d, 1H, J ¼ 3.4 Hz, furan-H), 7.50 (d, 1H,
J ¼ 3.4 Hz,furan-H),7.53(d,2H, J ¼ 8 Hz,4-methylthiophenyl),