V. Turukarabettu et al.
130.2, 129, 128.3, 127.8, 126.1, 117.3, 114.1, 111.8, 21.2
(DMSO-d6): δ=8.14 (s, 1H,=C–H), 8.04 (d, 1H, J=4.4 Hz,
NT-4H), 7.54 (d, 1H, J= 4.4 Hz, NT-3H), 7.42–7.84 (m,
9H) ppm; 13C NMR (DMSO-d6): δ = 187.7 (C=O), 166.7
(1JC-F =230 Hz, Ar C-F), 164.8, 160.2, 151.9, 146.8, 139.5,
133.2 (3JC-F, 12.4 Hz, Ar C-F), 133, 132.5 (2JC-F =39 Hz, Ar
C-F), 130.2, 129.7, 128.8, 126.9, 122.8, 116.7, 116.5 ppm;
MS: m/z=454.2 ([M+1]+).
(CH3) ppm; MS: m/z=434 ([M+1]+).
1‑(4‑Methoxyphenyl)‑3‑(5‑nitrofuran‑2‑yl)‑3‑(5‑phenyl‑1,3,4‑
oxadiazol‑2‑ylthio)prop‑2‑en‑1‑one (7c, C22H15N3O6S) Yel-
low crystalline; IR (KBr): v̄ = 1637 (C=O), 1597 (C=C),
1
1516 (C=N), 966 (C-S) cm−1; H NMR (CDCl3): δ=7.93
(s, 1H,=C-H), 7.02 (d, 1H, J=4 Hz, NF-4H), 6.99–8.07 (m,
9H), 6.83 (d, 1H, J=3.6 Hz, NF-3H), 3.90 (s, 3H, OCH3)
ppm; 13C NMR (DMSO-d6): δ=188.7 (C=O), 166.7, 160.7,
151.7, 145.4, 135.6, 134.0, 132.8, 130.1, 129.9, 129.5, 129.4,
127.0, 123.1, 114.6, 52.4 (OCH3) ppm; MS: m/z=449.50
([M+1]+).
3‑[5‑(2‑Hydroxyphenyl)‑1,3,4‑oxadiazol‑2‑ylthio]‑3‑
(5‑nitrothiophen‑2‑yl)‑1‑phenylprop‑2‑en‑1‑one (7h,
C21H13N3O5S2) Yellow crystalline; IR (KBr): v̄ = 1633
1
(C=O), 1589 (C=C), 1543 (C=N), 900 (C-S) cm−1; H
NMR (CDCl3): δ=9.69 (s, 1H, OH), 7.98 (s, 1H, =C-H),
7.95 (d, 2H, J=8 Hz), 7.25 (d, 1H, J=4 Hz, NT-4H), 6.94–
7.60 (m, 9H), 6.86 (d, 1H, J=4 Hz, NT-3H), 2.44 (s, 3H,
CH3) ppm; 13C NMR (CDCl3): δ=186.2 (C=O), 166, 158.7,
157.2, 150.5, 147.1, 135.7, 133.4, 132.3, 131.4, 130.8,
129.8, 129.5, 127.5, 120.1, 117.5, 117.2, 114.2, 110.2 ppm;
MS: m/z=451.45 ([M+1]+).
1‑(4‑Chlorophenyl)‑3‑(5‑nitrofuran‑2‑yl)‑3‑(5‑phenyl‑1,3,4‑
oxadiazol‑2‑ylthio)prop‑2‑en‑1‑one (7d, C21H12ClN3O5S) Yel-
low crystalline; IR (KBr): v̄ = 1627 (C=O), 1585 (C=C),
1
1537, 1523 (C=N), 970 (C–S) cm−1; H NMR (DMSO-
d6): δ=8.27 (s, 1H,=C-H), 7.61 (d, 1H, J=4 Hz, NF-4H),
7.46–8.26 (m, 9H), 7.43 (d, 1H, J=5.6 Hz, NF-3H) ppm;
13C NMR (DMSO-d6): δ=189 (C=O), 170.5, 165.7, 155.8,
155.5, 135.3, 135.2, 132.5, 130.7, 131.9, 130.7, 129.3, 127,
125, 120.5, 115.2 ppm; MS: m/z=453.40 ([M+1]+), 455.40
([M+3]+) (37Cl), with peak intensity ratio of 3:1.
3‑[5‑(2‑Hydroxyphenyl)‑1,3,4‑oxadiazol‑2‑ylthio]‑3‑(5‑nitro‑
furan‑2‑yl)‑1‑(p‑tolyl)prop‑2‑en‑1‑one (7i, C22H15N3O6S) Yel-
low crystalline; IR (KBr): v̄ = 3309 (O–H), 1624 (C=O),
1
1591 (C=C), 1543 (C=N), 894 (C–S) cm−1; H NMR
(CDCl3): δ=9.69 (s, 1H, OH), 7.95 (d, 2H, J=8 Hz, ArH),
7.98 (s, 1H, = C-H), 7.58 (d, 1H, J = 8 Hz, ArH), 7.43 (t,
1H, J=7.2 Hz, 6.8 Hz, salicyl-4H), 7.32 (d, 2H, J=8.4 Hz,
ArH), 7.25 (d, 1H, J=4 Hz, NF-4H), 7.06 (d, 1H, J=8.4 Hz,
ArH), 6.93 (t, 1H, J = 7.6 Hz, 8 Hz, salicyl-5H), 6.86 (d,
1H, J = 4 Hz, NF-3H), 2.44 (s, 3H, CH3), ppm; 13C NMR
(CDCl3): δ=188.5 (C=O), 167, 157.5, 159.9, 151.3, 145.5,
135.2, 134.5, 132.1, 130.2, 129.5, 129, 126.5, 120.1, 118.5,
115.2, 113.2, 107.2, 22 (CH3) ppm; MS: m/z = 449.55
([M+1]+).
3‑(5‑Nitrothiophen‑2‑yl)‑1‑phenyl‑3‑[5‑(p‑tolyl)‑1,3,4‑oxa‑
diazol‑2‑ylthio]prop‑2‑en‑1‑one (7e, C22H15N3O4S2) Yellow
crystalline; IR (KBr): v̄ =1637 (C=O), 1589 (C=C), 1548
(C=N), 950 (C–S) cm−1; 1H NMR (DMSO-d6): δ=8.09 (s,
1H,=C-H), 8.04 (d, 2H, J=8.4 Hz), 7.99 (d, 1H, J=4.4 Hz,
NT-4H), 7.79 (d, 2H, J=7.6 Hz), 7.53–7.60 (m, 3H), 7.50
(d, 1H, J=4.4 Hz, NT-3H), 7.37 (d, 2H, J=8 Hz), 2.38 (s,
3H, CH3) ppm; 13C NMR (DMSO-d6): δ = 188.7 (C=O),
166.7, 160.3, 151.8, 146.9, 145.4, 138.7, 134, 132.9, 130.2,
130, 129.9, 129.5, 129.3, 126.9, 122.8, 21.7 ppm; MS:
m/z=449.50 ([M+1]+).
3‑[5‑(2‑Hydroxyphenyl)‑1,3,4‑oxadiazol‑2‑ylthio]‑1‑(4‑me‑
thoxyphenyl)‑3‑(5‑nitrothiophen‑2‑yl)prop‑2‑en‑1‑one‑
(7j, C22H15N3O6S2) Yellow crystalline; IR (KBr): v̄ = 3327
(O–H), 1624 (C=O), 1589 (C=C), 1544 (C=N), 898 (C–S)
cm−1; 1H NMR (CDCl3): δ=9.66 (s, 1H, OH), 8.01 (d, 2H,
J = 7.2 Hz, ArH), 7.69 (d, 1H, J = 2 Hz, NT-4H), 7.60 (s,
1H, = C–H), 7.17 (d, 1H, J = 2 Hz, NT-3H), 7.06 (d, 1H,
J = 8.8 Hz, salicyl-3H), 6.93–7.52 (m, 8H), 6.93 (t, 1H,
J=7.2 Hz, 6.8 Hz, salicyl-4H), 3.90 (s, 3H, OCH3) ppm; 13C
NMR (CDCl3): δ=186.7 (C=O), 166.4, 164.5, 159.6, 157.5,
146.2, 134.3, 131.1, 129.3, 128.3, 128, 127.8, 126.3, 120.1,
117.8, 114.3, 107.2, 55.6 (OCH3) ppm; MS: m/z = 481.45
(M+).
1‑(4‑Methoxyphenyl)‑3‑(5‑nitrothiophen‑2‑yl)‑3‑
(5‑phenyl‑1,3,4‑oxadiazol‑2‑ylthio)prop‑2‑en‑1‑one (7f,
C22H15N3O5S2) Yellow crystalline; IR (KBr): v̄ = 1637
(C=O), 1595 (C=C), 1546, 1520 (C=N), 900 (C-S) cm−1;
1H NMR (CDCl3): δ = 8.01 (d, 2H, J = 8 Hz), 7.85 (d,
2H, J = 8.4 Hz), 7.65 (d, 1H, J = 4.4 Hz, NT-4H), 7.57
(s, 1H, = C–H), 7.43–7.57 (m, 3H), 7.15 (d, 1H, J= 4 Hz,
NT-3H), 6.99 (d, 2H, J=8.4 Hz, ArH), 3.90 (s, 3H, OCH3)
ppm; 13C NMR (CDCl3): δ = 186.7 (C=O), 164.4, 146.3,
132.3, 131, 129.4, 129.1, 128.3, 127.3, 126.7, 122.8, 114.3,
55.6 (OCH3) ppm; MS: m/z=465.55 ([M+1]+).
1 ‑ ( 4 ‑ Fl u o ro p h e ny l ) ‑ 3 ‑ ( 5 ‑ n i t ro t h i o p h e n ‑ 2 ‑ y l ) ‑ 3 ‑
(5‑phenyl‑1,3,4‑oxadiazol‑2‑ylthio)prop‑2‑en‑1‑one (7g,
In vivo anti‑infammatory activity
C
21H12FN3O4S2) Brown needles; IR (KBr): v̄ =1629 (C=O),
Male Wistar rats were taken, fasted for 12 h, and given free
access to water. Since the synthesized compounds were less
1
1600 (C=C), 1541 (C=N), 902 (C–S) cm−1; H NMR
1 3