An alternative way to analogues of avenanthramides and their antiradical activity
120.8, 125.6, 127.9, 131.6, 132.3, 138.9, 155.5, 160.9,
910, 885, 860, 830, 800, 765, 740, 690, 630, 590, 550, 520,
495, 470, 440 cm-1; HRMS: m/z = 344.1124.
ꢀ
164.5, 166.3 ppm; IR (KBr): m = 3855, 3740, 3620, 3260,
3135, 3010, 2960, 2935, 2840, 2645, 2535, 2360, 2345,
2040, 1680, 1650, 1600, 1570, 1540, 1515, 1475, 1460,
1430, 1260, 1215, 1175, 1125, 1065, 1025, 945, 915, 855,
3-(4-Hydroxyphenyl)-2-[[(4-methoxyphenyl)amino]carbo-
nyl]prop-2(E)-enoic acid (11aG, C17H15NO5) was obtained
from 2-(4-methoxyphenyl)carbamoylacetic acid (8a) and
4-hydroxybenzaldehyde (10G) by reflux in acetic acid for
18 h. Crystallization led to solid material (68%) with m.p.
208–210 °C. 1H NMR (300 MHz, DMSO-d6): d = 3.74
(3H, s, OCH3), 6.76 (2H, d, J = 8.6 Hz, H-30,50), 6.91 (2H,
d, J = 9.0 Hz, H-3,5), 7.46 (2H, d, J = 8.6 Hz, H-20,60),
7.50 (1H, s, H-b), 7.57 (2H, d, J = 9.0 Hz, H-2,6), 10.09
(1H, s, OH), 10.26 (1H, s, NH), 12.77 (1H, br. s, COOH)
ppm; 13C NMR (75.5 MHz, DMSO-d6): d = 55.2, 113.9,
115.8, 120.8, 124.1, 126.9, 131.9, 132.4, 139.4, 155.5,
835, 810, 780, 745, 725, 670, 615, 560, 535, 475 cm-1
;
HRMS: m/z = 328.1179.
3-(3-Bromophenyl)-2-[[(4-methoxyphenyl)amino]carbonyl]-
prop-2(E)-enoic acid (11aD) was obtained from 2-(4-
methoxyphenyl)carbamoylacetic acid (8a) and 3-bro-
mobenzaldehyde (10D) by reflux in acetic acid for 46.5 h.
Crystallization led to solid material (26%) with m.p.
1
200–201 °C. The compound is known and its H and 13C
NMR data correspond to literature [34].
ꢀ
159.7, 164.7, 166.4 ppm; IR (KBr): m = 3855, 3740, 3300,
3-(3-Hydroxyphenyl)-2-[[(4-methoxyphenyl)amino]car-
bonyl]prop-2(E)-enoic acid (11aE, C17H15NO5) was
obtained from 2-(4-methoxyphenyl)carbamoylacetic acid
(8a) and 3-hydroxybenzaldehyde (10E) by reflux in acetic
acid for 17 h. Crystallization led to solid material (66%)
with m.p. 181 °C. 1H NMR (300 MHz, DMSO-d6):
d = 3.73 (3H, s, OCH3), 6.81 (1H, dd, J = 8.0, 2.0 Hz, H-
40), 6.91 (2H, d, J = 9.0 Hz, H-3,5), 7.02 (1H, d,
J = 2.0 Hz, H-20), 7.03 (1H, d, J = 8.0, Hz, H-60), 7.18
(1H, t, J = 8.0 Hz, H-50), 7.50 (1H, s, H-b), 7.55 (2H, d,
J = 9.0 Hz, H-2,6), 9.62 (1H, s, OH), 10.26 (1H, s, NH),
12.95 (1H, br. s, COOH) ppm; 13C NMR (75.5 MHz,
DMSO-d6): d = 55.2, 113.9, 116.1, 117.4, 120.7, 120.9,
129.8, 130.3, 132.2, 134.4, 139.3, 155.5, 157.6, 164.0,
3120, 3025, 2960, 2900, 2835, 2690, 2615, 2510, 2360,
2345, 1650, 1625, 1600, 1585, 1560, 1510, 1475, 1455,
1445, 1420, 1380, 1300, 1270, 1250, 1205, 1175, 1120,
1105, 1075, 1040, 1010, 950, 940, 915, 840, 825, 810, 790,
725, 685, 595, 575, 545, 530, 515, 485, 420 cm-1
.
3-(4-Hydroxy-3-methoxyphenyl)-2-[[(2-methoxyphenyl)-
amino]carbonyl]prop-2(E)-enoic acid (11bA, C18H17NO6)
was obtained from 2-(2-methoxyphenyl)carbamoylacetic
acid (8b) and vanillin (10A) by reflux in acetic acid for 7 h.
Crystallization led to solid material (74%) with m.p. 187–
1
189 °C. H NMR (300 MHz, DMSO-d6): d = 3.56 (3H, s,
OCH3), 3.74 (3H, s, OCH3), 6.78 (1H, d, J = 8.2 Hz, H-50),
6.96 (1H, t, J = 7.6 Hz, H-5), 7.03 (1H, d, J = 8.2 Hz, H-
60), 7.08–7.15 (2H, m, H-3,4), 7.21 (1H, s, H-11), 7.47 (1H,
s, H-b), 8.11 (1H, d, J = 7.9 Hz, H-6), 9.62 (1H, s, OH),
9.68 (1H, s, NH), 12.66 (1H, br. s, COOH) ppm; 13C NMR
(75.5 MHz, DMSO-d6): d = 55.7, 56.1, 111.9, 113.4,
116.0, 120.8, 122.3, 125.0, 125.2, 125.3, 127.5, 127.6,
140.1, 147.9, 149.6, 150.2, 166.3, 166.7 ppm; IR (KBr):
ꢀ
166.2 ppm; IR (KBr): m = 3840, 3800, 3740, 3650, 3235,
3040, 3000, 2835, 2630, 2360, 2345, 1770, 1710, 1675,
1660, 1635, 1620, 1595, 1580, 1560, 1515, 1455, 1435,
1415, 1350, 1340, 1300, 1280, 1245, 1170, 1070, 1030,
1000, 965, 940, 920, 880, 830, 820, 810, 795, 775, 745,
695, 675, 600, 565, 520, 460 cm-1
.
ꢀ
m = 3840, 3735, 3650, 3545, 3495, 3355, 3010, 2960, 2835,
3-(3-Hydroxy-4-methoxyphenyl)-2-[[(4-methoxyphenyl)-
amino]carbonyl]prop-2(E)-enoic acid (11aF, C18H17NO6)
was obtained from 2-(4-methoxyphenyl)carbamoylacetic
acid (8a) and 3-hydroxy-4-methoxybenzaldehyde (10F) by
reflux in acetic acid for 31 h. Crystallization led to solid
material (37%) with m.p. 209–210 °C. 1H NMR
(300 MHz, DMSO-d6): d = 3.74 (3H, s, OCH3), 3.78 (3H,
s, OCH3), 6.85–6.98 (3H, m, H-3,5,50), 7.03–7.12 (2H, m,
H-20,60), 7.44 (1H, s, H-b), 7.58 (2H, d, J = 8.7 Hz, H-2,6),
9.16 (1H, s, OH), 10.24 (1H, s, NH), 12.79 (1H, br. s,
COOH) ppm; 13C NMR (75.5 MHz, DMSO-d6): d = 55.2,
55.6, 113.9, 113.9, 116.4, 120.9, 122.7, 126.0, 127.8,
132.4, 139.4, 146.4, 149.9, 155.5, 164.5, 166.4 ppm; IR
2645, 2530, 2360, 2345, 1660, 1620, 1590, 1560, 1520,
1485, 1460, 1440, 1430, 1390, 1375, 1315, 1305, 1285,
1255, 1225, 1205, 1185, 1130, 1115, 1065, 1045, 1025,
930, 900, 875, 810, 780, 770, 750, 730, 685, 635, 615, 580,
560, 515, 485, 455, 430 cm-1
.
3-(4-Hydroxy-3-methoxyphenyl)-2-[[(2-hydroxyphenyl)ami-
no]carbonyl]prop-2(E)-enoic acid (11cA, C17H15NO6) was
obtained from 2-(4-hydroxyphenyl)carbamoylacetic acid
(8c) and vanillin (10A) by reflux in acetic acid for 28 h.
Crystallization led to solid material (62%) with m.p. 174–
1
175 °C. H NMR (300 MHz, DMSO-d6): d = 3.57 (3H, s,
OCH3), 6.74–6.91 (2H, m, H-3,5,50), 6.99 (1H, td, J = 7.8,
1.6 Hz, H-4), 7.11 (1H, dd, J = 8.3, 1.8 Hz, H-60), 7.21
(1H, d, J = 1.8 Hz, H-20), 7.49 (1H, s, H-b), 7.85 (1H, dd,
J = 7.8, 1.6 Hz, H-6), 9.73 (1H, s, NH), 9.74 (2H, s, 2OH),
12.78 (1H, br. s, COOH) ppm; 13C NMR (75.5 MHz,
ꢀ
(KBr): m = 3840, 3800, 3735, 3675, 3650, 3395, 3195,
3135, 3060, 3000, 2940, 2845, 2630, 2360, 2345, 2045,
1685, 1635, 1600, 1580, 1560, 1540, 1510, 1465, 1455,
1420, 1380, 1340, 1315, 1180, 1135, 1080, 1030, 970, 940,
123