Med Chem Res
2-(4–(1-(3,4,5-Trimethoxyphenyl)-5-phenyl-1H-1,2,4-tria-
zole-3-carboxamido)phenyl)acetic acid (4k) A mixture of
compound 3c (0.01 mol, 2.66 g), 2-(4-aminophenyl)acetic
acid (0.012 mol) yielded yellowish white crystals (3.8 g,
78%); IR (cm−1): 3668 (OH), 3302 (NH), 1717 (C=O),
4-(1-(4-Chlorophenyl)-5-(3,4,5-trimethoxyphenyl)-1H-
1,2,4-triazole-3-carboxamido)benzoic acid (4n) Reaction
of 3d (0.01 mol, 3.89 g) with PABA (0.01 mol, 1.37 g)
yielded pale yellow crystals; 77.90% yield; mp 213 °C; IR
(KBr, cm−1): 3242–2535 (OH), 3329 (NH), 1718 (car-
boxylic C=O), 1670 (amidic C=O), 1580 (C=N); 1H-NMR
(400 MHz, DMSO-d6) δ (ppm): 3.64 (s, 6H, 2-OCH3), 3.71
(s, 3H, OCH3), 6.83 (s, 2H, Ar–H), 7.61 (d, 2H, J = 8.40
Hz, Ar–H), 7.68 (d, 2H, J = 8.40 Hz, Ar–H), 7.95 (d, 2H, J
= 8.40 Hz, Ar–H), 8.01 (d, 2H, J = 8.40 Hz, Ar–H), 8.69 (s,
1H, CONH); 13C-NMR (100 MHz, CDCl3) δ (ppm): 56.32,
60.67, 107.17, 120.41, 122.10, 126.52, 128.61,
130.08, 130.67, 134.87, 136.81, 139.75, 142.80, 153.22,
155.39, 156.33, 157.96, 167.36; HRMS: m/z calculated
1
1678 (C=O), 1590 (C=N); H-NMR (500 MHz, DMSO-
d6) δ (ppm): 3.65 (t, 2H, HOOC–CH2), 3.71 (s, 6H, 2
OCH3), 3.89 (s, 3H, 2 OCH3), 6.61 (s, 2H, 2Ar–H),
7.42–7.60 (m, 5H, Ar–H), 7.93 (d, 2H, J = 8 Hz, H2,6 of
benzoic acid ring), 8.00 (d, 2H, J = 8 Hz, H3,5 of benzoic
acid ring), 9.08 (s, 1H, NH); 13C-NMR (125 MHz, DMSO-
d6) δ (ppm): 40.16, 56.25, 64.05, 103.04, 120.03, 126.75,
126.87, 128.75, 129.57, 130.05, 130.71, 132.49, 136.61,
138.75, 153.52, 154.85, 156.21, 156.62, 175.76; HRMS:
m/z calculated for C17H14N4O3 [M–H]+: 487.16231, found:
487.16266.
for
507.10791.
C25H21ClN4O6[M–H]−:
507.10769,
found:
4–((1-(3,4,5-Trimethoxyphenyl)-5-phenyl-1H-1,2,4-tria-
zole-3-carboxamido)methyl) benzoic acid (4l) Reaction of
3c (0.01 mol, 3.56 g) with 4-(aminomethyl)benzoic acid
(0.012 mol, 1.81 g) yielded brownish white powder (3.51,
72%); mp 189–191 °C; IR ν (cm−1): 3610–2820 (OH),
4-((1-(4-Chlorophenyl)-5-(3,4,5-trimethoxyphenyl)-1H-
1,2,4-triazole-3-carboxamido)methyl)benzoic acid (4o)
Reaction
of
3d
(0.01 mol,
3.89 g)
with
4-
aminomethylbenzoic acid (0.01 mol, 1.51 g) yielded pale
yellow crystals; 73.40% yield; mp 213 °C; IR (KBr, cm−1):
3242–2535 (OH), 3329 (NH), 1718 (carboxylic C=O),
1669 (amidic C=O), 1588 (C=N); 1H-NMR (400 MHz,
CDCl3) δ (ppm): 3.64 (s, 6H, 2-OCH3), 3.72 (s, 3H, OCH3),
4.57 (d, 2H, J = 4.00 Hz, CH2NH), 6.79 (s, 2H, Ar–H),
7.46 (d, 2H, J = 8.00 Hz, Ar–H), 7.56 (d, 2H, J = 8.00 Hz,
Ar–H), 7.64 (d, 2H, J = 8.00 Hz, Ar–H), 7.92 (d, 2H, J =
8.00 Hz, Ar–H), 9.21 (t, 1H, J = 4.00 Hz, CONH), 12.70 (s,
1H, COOH); 13C-NMR (100 MHz, CDCl3) δ (ppm): 56.46,
60.67, 66.36, 107.45, 122.26, 127.83, 128.44, 129.81,
130.00, 134.73, 136.99, 139.5, 140.10, 144.85, 153.29,
155.10, 156.74, 159.28, 167.60; HRMS: m/z calculated for
C26H23ClN4O6[M–H]−: 521.12334, found: 521.12347.
1
3300 (NH), 1720 (C=O), 1670 (C=O), 1602 (C=N); H-
NMR (500 MHz, DMSO-d6) δ (ppm): 3.67 (s, 6H, 2
OCH3), 3.71 (s, 3H, OCH3), 4.55 (d, 2H, J = 6.2 Hz,
NH–CH2), 6.81 (s, 2H, H2,6 of Ar–H), 7.45 (d, 2H, J = 8.5
Hz, H3,5 of benzoic acid ring), 7.47–7.56 (m, 5H, Ar–H),
7.74 (d, 2H, J = 8.5 Hz, H2.6 of benzoic acid ring), 9.35 (t,
1H, J = 6.2 Hz, NH), 12.85 (s, 1H, COOH); 13C-NMR
(125 MHz, DMSO-d6): 42.54, 56.63, 60.71, 104.55,
127.53, 127.73, 129.10, 129.8, 130.81, 133.45, 138.55,
144.94, 149.98, 153.46, 154.99, 156.33, 159.28, 167.61;
HRMS: m/z calculated for C26H24N4O6 [M–H]−:
487.16231, found: 487.16269.
3-(1-(4-Chlorophenyl)-5-(3,4,5-trimethoxyphenyl)-1H-
1,2,4-triazole-3-carboxamido)propanoic acid (4m) Reac-
tion of 3d (0.01 mol, 3.89 g) with β-alanine (0.01 mol, 0.89
g) yielded pale yellow crystals; 47% yield; mp 185 °C; IR
(KBr, cm−1): 3320–2535 (OH), 3355 (NH), 1715 (car-
boxylic C=O), 1661 (amidic C=O), 1610 (C=N); 1H-NMR
(400 MHz, CDCl3) δ (ppm): 2.77 (t, 2H, J = 6.40 Hz,
CH2CO), 3.71 (s, 6H, 2-OCH3), 3.82 (q, 2H, J = 6.40 Hz,
CH2NH), 3.90 (s, 3H, OCH3), 6.70 (s, 2H, Ar–H), 7.39 (d,
2H, J = 8.40 Hz, Ar–H), 7.46 (d, 2H, J = 8.40 Hz, Ar–H),
7.90 (t, 1H, J = 6.40 Hz, CONH); 13C-NMR (100 MHz,
CDCl3) δ (ppm): 33.63, 34.93, 56.13, 60.98, 106.54,
121.24, 126.96, 129.67, 135.59, 136.20, 140.29,
153.33, 155.02, 156.23, 159.10, 175.61; HRMS: m/z cal-
culated for C21H21ClN4O6 [M–H]−: 459.10769, found:
459.10703.
Ethyl4-(1-(4-chlorophenyl)-5-(3,4,5-trimethoxyphenyl)-1H-
1,2,4-triazole-3-carboxamido)benzoate (4p) Reaction of
3d (0.01 mol, 3.89 g) with benzocaine (0.01 mol, 1.65 g)
yielded pale yellow crystals; 87.60% yield; mp 177 °C; IR
1
(KBr, cm−1): 3329 (NH2), 1669 (C=O), 1588 (C=N); H-
NMR (400 MHz, CDCl3) δ (ppm): 1.42 (t, 3H, J = 6.40 Hz,
CH2CH3), 3.74 (s, 6H, 2-OCH3), 3.91 (s, 3H, OCH3), 4.38
(q, 2H, J = 6.40 Hz, CH2CH3), 6.75 (s, 2H, Ar–H), 7.43 (d,
2H, J = 8.00 Hz, Ar–H), 7.50 (d, 2H, J = 8.00 Hz, Ar–H),
7.88 (d, 2H, J = 8.40 Hz, Ar–H), 8.10 (d, 2H, J = 8.40 Hz,
Ar–H), 9.27 (s, 1H, CONH); 13C-NMR (100 MHz, CDCl3)
δ (ppm): 14.36, 56.17, 60.94, 61.03, 106.48, 119.12,
120.96, 126.52, 126.97, 129.52, 130.89, 135.83, 136.09,
140.44, 141.33, 153.41, 155.08, 155.94, 156.42, 166.06;
HRMS: m/z calculated for C27H25ClN4O6[M–H]−:
535.13899, found: 535.13971.