S.H. Emam et al.
Bioorganic Chemistry 107 (2021) 104630
the reported procedures. Chalcones (E)-1-(3,4-dimethoxyphenyl)-3-(4-
morpholinophenyl)prop-2-en-1-one (2h) [49], (E)-3-(4-(piperidin-1-yl)
phenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (2j) [50] and (E)-3-
4.38.
3-(4-(4-methoxyphenoxy)phenyl)-1-(3,4,5-trimethoxyphenyl)
◦
prop-2-en-1-one (2f): Yellow solid: 90% yield; mp 138–140 C; IR (KBr,
ꢀ 1
–
–
cm ) 3066 (CH aromatic), 2947, 2932 (CH aliphatic), 1654 (C O),
(
4-morpholinophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
(2k)
–
1
[
49] were prepared in the mentioned references.
1573 (C
–
C); H NMR (400 MHz, DMSO‑d
CH–
6
) δ 7.92–7.88 (m, 2H, ArH),
–
–
7
.85 (d, J = 15.6 Hz, 1H, CH
CO), 7.72 (d, J = 15.6 Hz, 1H,
CH CO), 7.42 (s, 2H, ArH), 7.10–7.06 (m, 2H, ArH), 7.02–6.99
), 3.78 (s, 3H,
); C NMR (100 MHz, DMSO‑d
) δ:188.2
O), 160.6, 156.5, 153.3, 149.9, 143.7, 142.3, 133.5, 131.4, 129.5,
121.6, 120.9, 117.4, 115.6, 106.5, 106.2, 60.6, 56.6, 55.8; Anal. Calcd
for C25 (420.45): C, 71.41; H, 5.75, found C, 71.68; H, 5.94.
1-(3,4-dimethoxyphenyl)-3-(4-(piperidin-1-yl)phenyl)prop-2-en-
–
–
–
4
.1.2. General procedure for the preparation of methoxyphenyl chalcones
a-l
To an ice cooled, stirred solution of the selected aldehyde (0.01 mol)
1a-f) and 3,4-dimethoxyacetophenone or 3,4,5-trimethoxyacetophe-
CH
2
(m, 2H, ArH), 6.98–6.96 (m, 2H, ArH), 3.90 (s, 6H, 2 OCH
OCH
3
1
3
3
), 3.77 (s, 3H, OCH
3
6
–
–
(
(C
none (0.01 mol) in 95% ethanol, was added portion wise 40%
◦
aqueous KOH solution. Stirring was continued at 0 C for 6 h. Solid
24 6
H O
product was filtered and washed with 3% aqueous HCl and crystallized
from ethanol.
ꢀ
1
1-one (2g): Yellow oil: 84% yield; IR (KBr, cm ) 3085 (CH aromatic),
–
–
–
–
1
3
-(4-(4-chlorophenoxy)phenyl)-1-(3,4-dimethoxyphenyl)prop-2-
2960, 2939 (CH aliphatic), 1654 (C
MHz, CDCl
) δ 7.78 (d, J = 15.6 Hz, 1H, CH
2.0, 8.4 Hz, 1H, ArH), 7.62 (d, J = 2.0 Hz, 1H, ArH), 7.54 (d, J = 8.4 Hz,
O), 1580 (C
–
C); H NMR (400
◦
ꢀ 1
–
–
en-1-one (2a): Yellow solid: 90% yield; mp 146–148 C; IR (KBr, cm
066 (CH aromatic), 2970, 2935 (CH aliphatic), 1651 (C
)
3
CH
CO), 7.68 (dd, J =
–
3
–
O), 1597,
–
–
1
– –
–
1
573 (C
–
C); H NMR (400 MHz, DMSO‑d
6
) δ 7.95–7.87 (m, 4H, ArH +
1H, ArH), 7.39 (d, J = 15.6 Hz, 1H, CH
ArH), 3.96 (s, 3H, OCH
2CH
2H, CH
CH CO), 6.93–6.88 (m, 3H,
), 3.95 (s, 3H, OCH
), 3.30 (t, J = 5.2 Hz, 4H,
piperidine), 1.72–1.66 (m, 4H, 2CH piperidine), 1.65–1.60 (m,
piperidine); C NMR (100 MHz, CDCl
) δ:188.8, 153.0, 152.8,
149.1, 144.6, 131.9, 130.1, 124.6, 122.6, 117.4, 114.9, 110.8, 109.9,
56.1, 56.0, 49.1, 25.4, 24.3; Anal. Calcd for C22 25NO (351.44): C,
75.19; H, 7.17; N, 3.99, found C, 75.02; H, 7.39; N, 4.25.
–
– –
–
CH
–
CH CO), 7.71 (d, J = 15.6 Hz, 1H, CH CH CO), 7.61 (d, J = 2.0
3
3
Hz, 1H, ArH), 7.50–7.46 (m, 2H, ArH), 7.14–7.07 (m, 5H, ArH), 3.88 (s,
2
2
1
3
13
3
1
1
H, OCH
3
), 3.86 (s, 3H, OCH
3
); C NMR (100 MHz, DMSO‑d
6
) δ:187.7,
2
3
58.7, 155.2, 153.6, 149.2, 142.7, 131.3, 131.0, 130.8, 130.5, 128.3,
23.7, 121.5, 121.3, 119.0, 111.3, 111.2, 56.2, 56.0; Anal. Calcd for
H
3
C
23
H
4
19ClO (394.85): C, 69.96; H, 4.85; found C, 70.18; H, 5.07.
3
-(4-(4-bromophenoxy)phenyl)-1-(3,4-dimethoxyphenyl)prop-2-
1-(3,4-dimethoxyphenyl)-3-(4-(4-methylpiperazin-1-yl)phenyl)
◦
ꢀ 1
◦
en-1-one (2b): Yellow solid: 91% yield; mp 184–186 C; IR (KBr, cm
062 (CH aromatic), 2966, 2935 (CH aliphatic), 1651 (C
)
prop-2-en-1-one (2i): Yellow solid: 80% yield; mp 173–175 C; IR (KBr,
–
ꢀ 1
–
–
cm ) 3082 (CH aromatic), 2962, 2939 (CH aliphatic), 1643 (C O),
3
–
O), 1597,
–
–
1
–
1
1
570 (C
–
C); H NMR (400 MHz, DMSO‑d
6
) δ 7.96–7.88 (m, 4H, ArH +
1589 (C
– –
1H, ArH), 7.75–7.71 (m, 3H, ArH + CH
–
–
C); H NMR (400 MHz, DMSO‑d
6
) δ 7.87 (dd, J = 2.0, 8.4 Hz,
–
– –
CH
–
CH CO), 7.71 (d, J = 15.6 Hz, 1H, CH
–
CH CO), 7.62–7.58 (m,
), 3.87 (s, 3H,
) δ:187.7, 158.6, 155.7, 153.6,
CH CO), 7.64 (d, J = 15.6 Hz,
CH CO), 7.60 (d, J = 2.0 Hz, 1H, ArH), 7.09 (d, J = 8.4 Hz,
1H, ArH), 6.98 (d, J = 8.4 Hz, 2H, ArH), 3.87 (s, 3H, OCH ), 3.86 (s, 3H,
OCH piperazine), 2.44 (t, J = 4.8 Hz, 4H,
), 3.28 (t, J = 4.8 Hz, 4H, 2CH
2CH piperazine), 2.22 (s, 3H, NCH
–
–
–
3
H, ArH), 7.12–7.04 (m, 5H, ArH), 3.88 (s, 3H, OCH
3
1H, CH
1
3
OCH
3
); C NMR (100 MHz, DMSO‑d
6
3
1
1
6
49.2, 142.7, 133.4, 131.3, 131.0, 130.8, 123.8, 121.7, 121.5, 119.1,
3
2
1
3
16.2, 111.3, 111.1, 56.2, 56.0; Anal. Calcd for C23
2.88; H, 4.36; found C, 63.15; H, 4.49.
H19BrO
4
(439.30): C,
2
3 6
); C NMR (100 MHz, DMSO‑d )
δ:187.5, 153.3, 152.8, 149.1, 144.1, 131.4, 130.8, 124.9, 123.3, 117.8,
114.7, 111.2, 111.1, 56.1, 56.0, 54.8, 47.3, 46.2; Anal. Calcd for
1
-(3,4-dimethoxyphenyl)-3-(4-(4-methoxyphenoxy)phenyl)prop-
◦
2
-en-1-one (2c): Yellow solid: 81% yield; mp 122–124 C; IR (KBr,
22 26 2 3
C H N O (366.45): C, 72.11; H, 7.15; N, 7.64, found C, 72.34; H,
ꢀ
1
–
cm ) 3078 (CH aromatic), 2943, 2912 (CH aliphatic), 1651 (C
–
O),
7.26; N, 7.88.
–
–
1
1
590, 1566 (C
–
C); H NMR (400 MHz, DMSO‑d
6
) δ 7.90–7.83 (m, 4H,
3-(4-(4-methylpiperazin-1-yl)phenyl)-1-(3,4,5-trimethoxyphenyl)
–
–
– –
◦
ArH + CH
CH CO), 7.69 (d, J = 15.6 Hz, 1H, CH
–
CH CO), 7.60 (d,
prop-2-en-1-one (2L): Yellow solid: 80% yield; mp 188–190 C; IR (KBr,
ꢀ 1
–
–
cm ) 3005 (CH aromatic), 2960, 2939 (CH aliphatic), 1647 (C O),
J = 2.0 Hz, 1H, ArH), 7.12–7.06 (m, 3H, ArH), 7.03–7.00 (m, 2H, ArH),
–
1
6
3
1
1
.99–6.95 (m, 2H, ArH), 3.88 (s, 3H, OCH
3
), 3.86 (s, 3H, OCH
) δ:187.7, 160.5, 156.5, 153.6,
49.2, 148.9, 143.0, 131.2, 131.0, 129.6, 123.7, 121.7, 120.9, 117.5,
15.6, 111.3, 111.1, 56.2, 56.0, 55.89; Anal. Calcd for C24
3
), 3.78 (s,
1566 (C
–
C); H NMR (400 MHz, DMSO‑d
CO), 7.67 (d, J = 15.6 Hz, 1H, CH
ArH), 6.98 (d, J = 8.4 Hz, 2H, ArH), 3.90 (s, 6H, 2OCH
OCH piperazine), 2.44 (t, J = 4.8 Hz, 4H,
), 3.29 (t, J = 4.8 Hz, 4H, 2CH
2CH piperazine), 2.22 (s, 3H, NCH
δ:188.0, 153.3, 152.9, 144.9, 142.0, 134.0, 131.1, 124.7, 117.8, 114.6,
106.3, 60.6, 56.6, 54.8, 47.2, 46.1; Anal. Calcd for C23 (396.48)
C, 69.67; H, 7.12; N, 7.07, found C, 69.91; H, 7.28; N, 7.29.
6
) δ 7.76–7.70 (m, 3H, ArH +
1
3
–
–
–
–
–
CH
H, OCH
3
); C NMR (100 MHz, DMSO‑d
6
CH
CH
–
CO), 7.40 (s, 2H,
), 3.76 (s, 3H,
3
H
22
O
5
3
2
1
3
(
390.43): C, 73.83; H, 5.68, found C, 73.60; H, 5.85.
2
3 6
); C NMR (100 MHz, DMSO‑d )
3
-(4-(4-chlorophenoxy)phenyl)-1-(3,4,5-trimethoxyphenyl)prop-
◦
2
-en-1-one (2d): Yellow solid: 89% yield; mp 160–162 C; IR (KBr,
28 2 4
H N O
ꢀ
1
–
–
cm ) 3093 (CH aromatic), 2993, 2935 (CH aliphatic), 1654 (C
O),
) δ 7.97–7.95 (m, 2H, ArH),
CO), 7.75 (d, J = 15.6 Hz, 1H,
–
–
–
CH CO), 7.50–7.46 (m, 2H, ArH), 7.43 (s, 2H, ArH), 7.15–7.08
–
–
1
1
570 (C
C); H NMR (400 MHz, DMSO‑d
CH–
6
–
–
7
.89 (d, J = 15.6 Hz, 1H, CH
4.1.3. General procedure for the preparation of substituted 2H-chromen-2-
one chalcone derivatives (3a-f)
CH
1
3
(
m, 4H, ArH), 3.91 (s, 6H, 2 OCH
MHz, DMSO‑d
) δ:188.2, , 158.8, 155.2, 153.3, , 143.5, 142.4, 133.5,
31.5, 130.7, 130.5, 128.3, 121.5, 121.3, 119.0, 106.6, , 60.6, 56.6;
3
), 3.77 (s, 3H, OCH
3
); C NMR (100
A mixture of 3-acetyl-2H-chromen-2-one (1.88 g, 0.01 mol) and the
selected aldehyde (1a-f) were dissolved in 95% ethanol (50 mL).
Piperidine (0.085 g, 0.001 mol) was added and the mixture was heated
under reflux for 6 h. After cooling the solid product was filtered, washed
with ethanol, dried, and crystallized from ethanol.
6
1
Anal. Calcd for C24
H, 5.24.
5
H21ClO (424.87): C, 67.85; H, 4.98, found, C, 67.98;
3
-(4-(4-bromophenoxy)phenyl)-1-(3,4,5-trimethoxyphenyl)prop-
3-(3-(4-(4-chlorophenoxy)phenyl)acryloyl)–2H-chromen-2-one
◦
◦
ꢀ 1
2
-en-1-one (2e): Yellow solid: 89% yield; mp 190–192 C; IR (KBr,
(3a): Orange solid: 61% yield; mp 178–180 C; IR (KBr, cm ) 3082 (CH
ꢀ
1
–
–
–
–
C); 1H NMR (400 MHz,
cm ) 3088 (CH aromatic), 2997, 2935 (CH aliphatic), 1654 (C
O),
) δ 7.99–7.96 (m, 2H, ArH),
CO), 7.75 (d, J = 15.6 Hz, 1H,
–
–
–
CH CO), 7.63–7.59 (m, 2H, ArH), 7.43 (s, 2H, ArH), 7.13–7.05
aromatic), 1724, 1678 (2C
–
O), 1608 (C
–
–
–
1
1
570 (C
C); H NMR (400 MHz, DMSO‑d
CH–
6
DMSO‑d
6
) δ 8.61 (s, 1H, C4H of chromene), 8.41 (d, J = 8.0 Hz, 1H,
–
–
7
.89 (d, J = 15.6 Hz, 1H, CH
ArH), 8.24 (s, 1H, ArH), 7.86 (d, J = 7.6 Hz, 1H, ArH), 7.71 (t, J = 7.6
Hz, 1H, ArH), 7.64 (t, J = 8.0 Hz, 1H, ArH), 7.54–7.41 (m, 6H, ArH),
7.21–7.13 (m, 1H, ArH), 7.05–7.00 (m, 1H, ArH), 6.83–6.75 (m, 1H,
CH
1
3
(
m, 4H, ArH), 3.91 (s, 6H, 2 OCH
MHz, DMSO‑d
) δ:188.2, 158.7, 155.7, 153.3, 143.0, 142.4, 133.5,
33.4, 131.5, 130.7, 121.7, 121.5, 119.1, 116.2, 106.6, 60.6, 56.6; Anal.
Calcd for C24 21BrO (469.32): C, 61.42; H, 4.51, found C, 61.70; H,
3 3
), 3.78 (s, 3H, OCH ); C NMR (100
ArH); 13C NMR (100 MHz, DMSO‑d
) δ:189.1, 164.4, 161.3, 153.7,
150.7, 143.4, 133.1, 131.5, 129.5, 125.7, 125.2, 124.6, 118.2, 117.8,
116.5, 113.4, 99.9; Anal. Calcd for C24 15ClO (402.83): C, 71.56; H,
6
6
1
H
5
H
4
7