16
C. Borsari et al. / European Journal of Medicinal Chemistry 183 (2019) 111676
þ
calcd. for C23
21
H O
5
S [MþH] 409.1104, found 409.1102. Anal. calcd.
21 18 4
C H O S: C, 68.83; H, 4.95; S, 8.75; Found C, 69.18; H, 5.03; S, 8.53.
for C23 S: C, 67.63; H, 4.94; S, 7.85; Found C, 67.81; H, 5.05; S,
20 5
H O
7.67.
5.3.39. (E)-3-(furan-2-yl)-1-(2-hydroxy-5-methoxyphenyl)prop-2-
en-1-one (39)
5
3
.3.35. 2-(benzo[b]thiophen-3-yl)-6-methoxy-4-oxo-4H-chromen-
-yl pentanoate (35)
Compound 35 was prepared according to the general method
Compound 39 was prepared according to the general method
for the synthesis of (2E)-1-(2-hydroxyphenyl)-3-phenylprop-2-en-
1-ones reported above. Compound 39 was isolated as a red powder
ꢀ
1
for the synthesis of ethers reported above starting from compound
9. Compound 35 was isolated as a pale yellow solid in 53% yield.
in 51% yield. mp: 73e74 C. H NMR (CDCl , 400 MHz) d: 12.51 (br s,
3
1
1H), 7.71 (d, J ¼ 15.1 Hz, 1H), 7.59 (d, J ¼ 1.8 Hz, 1H), 7.52 (d,
J ¼ 15.1 Hz, 1H), 7.38 (d, J ¼ 3.0 Hz, 1H), 7,17 (dd, J ¼ 9.1, 3.0 Hz, 1H),
6.99 (d, J ¼ 9.1 Hz, 1H), 6.81 (d, J ¼ 3.4 Hz, 1H), 6.58 (dd, J ¼ 1.8,
ꢀ
1
3
mp: 111e112 C. H NMR (400 MHz, CDCl ) d: 8.13-8.11 (m, 1H), 8.05
(
1
s, 1H), 7.96-7.93 (m, 1H), 7.66 (d, J ¼ 3.1 Hz, 1H), 7.51 (d, J ¼ 9.2 Hz,
13
H), 7.51-7.42 (m, 2H), 7.32 (dd, J ¼ 9.2, 3.1 Hz, 1H), 3.92 (s, 3H), 2.55
3
3.4 Hz,1H), 3.87 (s, 3H). C NMR (CDCl ,100 MHz) d: 192.94,157.99,
(
t, J ¼ 7.5 Hz, 2H), 1.69-1.61 (m, 2H), 1.38-1.28 (m, 2H), 0.88 (t,
151.76, 151.54, 145.47, 131.25, 124.12, 119.64, 119.32, 117.60, 117.24,
13
þ
-
J ¼ 7.4 Hz, 3H). C NMR (100 MHz, CDCl
3
)
d
: 171.79, 170.87, 157.12,
112.95, 112.56, 56.12. MS (ESI) m/z ¼ 245.1 [MþH] ; 243.0 [M ꢃ H] .
1
53.22, 150.44, 139.75, 136.56, 133.65, 131.39, 125.47, 125.25, 125.22,
1
2
24.55, 124.27, 123.88, 122.78, 119.46, 105.08, 55.99, 33.64, 26.88,
5.3.40. (E)-3-(furan-2-yl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-
en-1-one (40)
Compound 40 was prepared according to the general method
for the synthesis of (2E)-1-(2-hydroxyphenyl)-3-phenylprop-2-en-
þ
2.08, 13.67. ESI-HRMS calcd. for C23
H
21
O
5
S [MþH] 409.1104,
found 409.1100. Anal. calcd. for C23
Found C, 67.33; H, 4.83; S, 8.01.
H
20
O
5
S: C, 67.63; H, 4.94; S, 7.85;
1
-ones reported above. Compound 40 was isolated as an orange
ꢀ
1
5
3
.3.36. 2-(benzo[b]thiophen-3-yl)-6-methoxy-4-oxo-4H-chromen-
-yl dimethylcarbamate (36)
Compound 36 was prepared according to the general method
solid in 65% yield. mp: 118e120 C. H NMR (CDCl , 400 MHz) d:
3
13.51 (br s, 1H), 7.83 (d, J ¼ 8.7 Hz, 1H), 7.65 (d, J ¼ 15.1 Hz, 1H), 7.55
(d, J ¼ 1.7 Hz, 1H), 7.48 (d, J ¼ 15.1 Hz, 1H), 6.74 (d, J ¼ 3.4 Hz, 1H),
6.53 (dd, J ¼ 1.7, 3.4 Hz, 1H), 6.49 (dd, J ¼ 8.7, 2.5 Hz, 1H), 6.48 (d, 1H,
for the synthesis of carbamates reported above starting from
compound 19. Compound 36 was isolated as a yellow solid in 42%
13
J ¼ 2.5 Hz, 1H), 3.86 (s, 3H). C NMR (CDCl
3
, 100 MHz) d: 191.45,
ꢀ
1
yield. mp: 221e222 C. H NMR (400 MHz, CDCl
.5 Hz, 1H), 8.11 (s, 1H), 7.94 (dd, J ¼ 7.2, 1.5 Hz, 1H), 7.66 (d,
J ¼ 3.1 Hz, 1H), 7.51 (d, J ¼ 9.1 Hz, 1H), 7.51-7.43 (m, 2H), 7.32 (dd,
3
)
d: 8.18 (dd, J ¼ 7.2,
166.61, 166.18, 151.66, 145.14, 131.24, 130.22, 117.90, 116.51, 114.15,
þ
1
112.77, 107.68, 101.05, 55.57. MS (ESI) m/z ¼ 245.1 [MþH] ; 243.1
-
[M ꢃ H] .
13
J ¼ 9.1, 3.1 Hz, 1H), 3.92 (s, 3H), 3.09 (s, 3H), 3.01 (s, 3H). C NMR
100 MHz, CDCl : 172.70, 156.98, 153.67, 153.40, 150.40, 139.78,
36.77, 134.33, 131.58, 125.54, 125.13, 125.11, 124.63, 124.10, 123.96,
(
1
3
)
d
5.3.41. (E)-1-(2-hydroxy-5-methoxyphenyl)-3-(4-methylthiophen-
2-yl)prop-2-en-1-one (41)
1
22.76, 119.40, 105.08, 55.95, 37.07, 36.83. ESI-HRMS calcd. for
Compound 41 was prepared according to the general method for
the synthesis of (2E)-1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-
ones reported above. Compound 41 was isolated as an orange
þ
C
C
4
21
H18NO
17NO
5
S [MþH] 396.0900, found 396.0908. Anal. calcd. for
21
H
5
S: C, 63.79; H, 4.33; N, 3.54; S, 8.11; Found C, 63.75; H,
ꢀ
1
.58; N, 3.50; S, 7.90.
solid in 73% yield. mp: 79 C. H NMR (CDCl , 400 MHz) d: 12.36 (br
3
s, 1H), 8.00 (d, J ¼ 15.1 Hz, 1H), 7.35 (d, J ¼ 15.1 Hz, 1H), 7.33 (d,
J ¼ 3.0 Hz, 1H), 7.23 (m, 1H), 7,15 (dd, J ¼ 9.0, 3.0 Hz, 1H), 7.08 (m,
5
.3.37. 2-(benzo[b]thiophen-3-yl)-3-ethoxy-6-methoxy-4H-
13
chromen-4-one (37)
Compound 37 was prepared according to the general method
for the synthesis of ethers reported above starting from compound
1H), 6.98 (d, J ¼ 9.0 Hz, 1H), 3.86 (s, 3H), 2.30 (d, J ¼ 0.7 Hz, 3H).
C
3
NMR (CDCl , 100 MHz) d: 192.79, 157.88, 151.69, 139.82, 139.29,
138.20, 134.81, 125.36, 123.66, 119.63, 119.28, 118.36, 112.93, 56.16,
þ
19. Compound 37 was isolated as a yellow solid in 77% yield. mp:
15.53. MS (ESI) m/z ¼ 275.1 [MþH] .
ꢀ
1
1
46e147 C. H NMR (400 MHz, CDCl
J ¼ 7.4, 0.9 Hz, 1H), 7.94 (dd, J ¼ 7.4, 1.1 Hz, 1H), 7.66 (d, J ¼ 3.1 Hz,
H), 7.52 (d, J ¼ 9.1 Hz, 1H), 7.51 (dd, J ¼ 7.0, 1.2 Hz, 1H), 7.44 (dd,
J ¼ 7.1, 0.9 Hz, 1H), 7.30 (dd, J ¼ 9.1, 3.1 Hz, 1H), 4.14 (q, J ¼ 7.0 Hz,
3
) d: 8.46 (s, 1H), 8.31 (dd,
5.3.42. (E)-1-(2-hydroxy-4-methoxyphenyl)-3-(4-methylthiophen-
2-yl)prop-2-en-1-one (42)
Compound 42 was prepared according to the general method
for the synthesis of (2E)-1-(2-hydroxyphenyl)-3-phenylprop-2-en-
1-ones reported above. Compound 42 was isolated as a yellow solid
1
13
2
H), 3.94 (s, 3H),1.27 (t, J ¼ 7.0 Hz, 3H). C NMR (100 MHz, CDCl
3
) d:
174.56, 156.79, 153.58, 149.91, 140.06, 139.68, 136.91, 132.31, 125.97,
ꢀ
1
125.04, 124.93, 124.32, 123.79, 122.79, 119.28, 104.73, 68.54, 55.97,
in quantitative yield. mp 123e124 C. H NMR (CDCl
ppm: 13.68 (br s, 1H), 7.94 (d, J ¼ 15.1 Hz, 1H), 7.78 (d, J ¼ 8.7 Hz,
1H), 7.31 (d, J ¼ 15.1 Hz,1H), 7.17 (s,1H), 7.03 (s,1H), 6.49 (dd, J ¼ 8.7,
3
, 400 MHz)
þ
1
3
5.61. ESI-HRMS calcd. for C20
53.0845. Anal. calcd. for C20
Found C, 67.92; H, 4.81; S, 9.11.
H
17
O
4
S [MþH] 353.0842, found
d
H
16
O
4
S: C, 68.17; H, 4.58; S, 9.10;
13
2.5 Hz, 1H), 3.86 (s, 3H), 2.32 (s, J ¼ 0.7 Hz, 3H). C NMR (CDCl
00 MHz) : 191.29, 166.62, 166.15, 140.02, 139.15, 137.02, 134.35,
131.10, 124.85, 118.62, 114.04, 107.67, 101.06, 55.57, 15.53. MS (ESI)
3
,
1
d
5
.3.38. 2-(benzo[b]thiophen-3-yl)-6-methoxy-3-propoxy-4H-
þ
-
chromen-4-one (38)
Compound 38 was prepared according to the general method
for the synthesis of ethers reported above starting from compound
m/z ¼ 275.1 [MþH] ; 273.0 [M ꢃ H] .
5.3.43. (E)-1-(2-hydroxy-5-methylphenyl)-3-(4-methylthiophen-2-
yl)prop-2-en-1-one (43)
19. Compound 38 was isolated as an orange solid in 76% yield. mp:
ꢀ
1
137 C. H NMR (400 MHz, CDCl
3
)
d
: 8.33 (s, 1H), 8.20 (d, J ¼ 7.4 Hz,
Compound 43 was prepared according to the general method
for the synthesis of (2E)-1-(2-hydroxyphenyl)-3-phenylprop-2-en-
1-ones reported above. Compound 43 was isolated as an orange
1
H), 7.85 (d, J ¼ 7.4, 1H), 7.57 (d, J ¼ 3.1 Hz, 1H), 7.44-7.33 (m, 2H),
7
.42 (d, J ¼ 9.2 Hz,1H), 7.21 (dd, J ¼ 9.1, 3.1 Hz,1H), 3.93 (t, J ¼ 6.7 Hz,
1
3
ꢀ
1
2
H), 3.85 (s, 3H), 1.66-1.50 (m, 2H), 0.77 (t, J ¼ 7.4 Hz, 3H). C NMR
: 174.51, 156.78, 153.41, 149.92, 140.31, 139.66,
36.95, 132.25, 125.95, 125.06, 125.02, 124.92, 124.27, 123.76,
solid in 60% yield. mp: 104e105 C. H NMR (400 MHz, CDCl ) d:
3
(
100 MHz, CDCl
3
)
d
12.71 (s, 1H), 7.99 (d, J ¼ 15.1 Hz, 1H), 7.65 (d, J ¼ 1.6 Hz, 1H), 7.41 (d,
J ¼ 15.1 Hz, 1H), 7.32 (dd, J ¼ 8.5, 2.1 Hz, 1H), 7.23 (s, 1H), 7.07 (s, 1H),
1
13
122.78, 119.28, 104.72, 74.56, 55.95, 23.35, 10.35. ESI-HRMS calcd.
6.94 (d, J ¼ 8.5 Hz, 1H), 2.38 (s, 3H), 2.31 (d, J ¼ 0.7 Hz, 3H). C NMR
þ
for C21
H
19
O
4
S [MþH] 367.0999, found 367.0998. Anal. calcd. for
3
(100 MHz, CDCl ) d: 193.07, 161.48, 139.92, 139.25, 137.85, 137.38,