DOI: 10.1080/14756366.2016.1222581
Activity of N-(benzoylphenyl)pyridine-3-carboxamide derivatives in hyperlipidemic rats
3
was added to the reaction mixture, followed by suction filtration (carbonyl), 1620 (amide carbonyl), 1589, 1535, 1450, 1411, 933,
to afford the final product.
ꢁ1
+
763, 709 cm . HRMS (ESI, negative mode): m/z [M-H ]
3
01.09748 (C H N O requires 301.09715).
19 13 2 2
N-(3-benzoylphenyl)pyridine-3-carboxamide (C4). A mixture of
-amino-benzophenone (C3, 0.63 g, Mwt 197.24, 3.2 mmol) and
3
2
-(2-[(pyridin-3-ylcarbonyl)amino]benzoyl)benzoic
0
acid
mixture of 2-amino-benzophenone-2 -carboxylic
nicotinoyl chloride (C2, 0.50 gm, Mwt 141.56, 3.5 mmol) was
used to produce N-(3-benzoylphenyl)pyridine-3-carboxamide as
pale yellow solid (C4, 0.50 gm, Mwt 302.3, 51.7%). R : 0.21
(
C10).
A
acid (C9, 0.77 gm, Mwt 241.24, 3.2 mmol) and nicotinoyl
chloride (C2, 0.50 gm, Mwt 141.56, 3.5 mmol) was used to
produce 2-(2-[(pyridin-3-ylcarbonyl)amino]benzoyl)benzoic acid
f
ꢀ
1
(
(
1
CHCl /MeOH, 96:4); Melting point: 154–156 C. H-NMR
3
500 MHz, DMSO-d ): d ¼ 10.67 (s, 1H, NH amide), 9.12 (m,
6
as pale yellow solid (C10, 0.115 g, Mwt 346.3, 10.4%). R : 0.51
f
H, Ar-H), 8.78 (d, J ¼ 3.4 Hz, 1H, Ar-H), 8.31 (d, J ¼ 7.9 Hz, 1H,
ꢀ
1
CHCl /MeOH, 96:4); Melting point: 238–239 C. H-NMR
(
(
(
3
Ar-H), 8.21 (s, 1H, Ar-H), 8.12 (d, J ¼ 8.1 Hz, 1H, Ar-H), 7.78 (d,
J ¼ 7.2, 2H, Ar-H), 7.71 (dd, J ¼ 7.4, 7.4 Hz, 1H, Ar-H), 7.57–
300 MHz, DMSO-d ): d ¼ 13.30 (broad s, 1H, COOH), 12.20
6
s, 1H, NH amide), 9.15 (m, 1H, Ar-H), 8.84 (d, J ¼ 4.4 Hz, 1H,
1
3
7
(
(
C
.61 (m, 4H, Ar-H), 7.51 (d, J ¼ 7.7, 1H, Ar-H) ppm. C-NMR
Ar-H), 8.65 (d, J ¼ 8.2 Hz, 1H, Ar-H), 8.32 (m, J ¼ 6.4, 7.8 Hz,
125 MHz, DMSO-d ): d ¼ 196.06 (ketone carbonyl), 164.80
6
1
H, Ar-H), 7.99 (d, J ¼ 7.5 Hz, 1H, Ar-H), 7.54–7.77 (m, 5H, Ar-
13
amide carbonyl), 152.75 (Ar-CH), 149.18 (Ar-CH), 139.50 (Ar-
Quaternary), 137.93 (Ar-C Quaternary), 137.47 (Ar-C
H), 7.27 (d, J ¼ 6.8 Hz, 1H, Ar-H), 7.17 (m, J ¼ 7.3, 7.5 Hz, 1H,
Ar-H) ppm. C-NMR (75 MHz, DMSO-d ): d ¼ 202.00 (ketone
6
Quaternary), 135.98 (Ar-CH), 133.21 (Ar-CH), 130.74 (Ar-C
Quaternary), 130.10 (2 Ar-CH), 129.57 (Ar-CH), 129.08 (2 Ar-
CH), 125.57 (Ar-CH), 124.65 (Ar-CH), 123.99 (Ar-CH), 121.75
carbonyl), 166.87 (COOH), 163.62 (amide carbonyl), 152.79 (Ar-
CH), 148.13 (Ar-CH), 141.17 (Ar-C Quaternary), 139.61 (Ar-C
Quaternary), 134.90 (Ar-CH), 134.64 (Ar-CH), 133.13 (Ar-CH),
(
1
1
Ar-CH) ppm. IR (KBr disk): ꢀ ¼ 3302 (NH amide), 3117, 3063,
132.42 (Ar-CH), 130.03 (Ar-CH), 129.94 (Ar-C Quaternary),
129.86 (Ar-CH), 129.54 (Ar-C Quaternary), 127.40 (Ar-CH),
124.27 (Ar-C Quaternary), 124.09 (Ar-CH), 123.37 (Ar-CH),
120.52 (Ar-CH) ppm. IR (KBr disk): ꢀ ¼ 3325 (NH amide),
2507–3240 (OH), 3039, 1959, 1928, 1836, 1820, 1643 (ketone
959, 1813, 1681 (ketone carbonyl), 1658 (amide carbonyl),
ꢁ1
589, 1550, 1481, 1427, 709 cm . HRMS (ESI, negative mode):
+
m/z [M-H ] 301.09560 (C H N O requires 301.09715).
9 13 2 2
1
carbonyl), 1627 (acid carbonyl), 1566 (amide carbonyl), 1481,
N-(4-benzoylphenyl)pyridine-3-carboxamide (C6). A mixture of
-amino-benzophenone (C5, 0.63 g, Mwt 197.24, 3.2 mmol) and
ꢁ1
1
mode): m/z [M + H ] 347.16389 (C H N O requires
435, 1396, 1242 (C-O), 763, 709 cm . HRMS (ESI, positive
+
4
2
0 15 2 4
nicotinoyl chloride (C2, 0.50 gm, Mwt 141.56, 3.5 mmol) was
used to produce N-(4-benzoylphenyl)pyridine-3-carboxamide as
pale yellow solid (C6, 0.87 gm, Mwt 302.3, 89.9%). R : 0.10
3
47.10263).
f
ꢀ
1
N-(2-benzoyl-5-methylphenyl)pyridine-3-carboxamide (C12).
mixture of 2-amino-4-methylbenzophenone (C11, 1.56 gm, Mwt
A
(
(
1
CHCl /MeOH, 96:4); Melting point: 158–160 C. H-NMR
3
500 MHz, DMSO-d ): d ¼ 10.80 (s, 1H, NH amide), 9.14 (m,
6
2
1
11.26, 7.4 mmol) and nicotinoyl chloride (C2, 0.50 gm, Mwt
41.56, 3.5 mmol) was used to produce N-(2-benzoyl-5-
H, Ar-H), 8.79 (d, J ¼ 3.8, 1H, Ar-H), 8.33 (d, J ¼ 7.9, 1H, Ar-
H), 7.99 (d, J ¼ 8.6, 2H, Ar-H), 7.81 (d, J ¼ 8.5, 2H, Ar-H), 7.74
methylphenyl)pyridine-3-carboxamide was obtained as pale
yellow solid (C12, 0.819 gm, Mwt 316.6, 35.0%). R : 0.70
(
7
d, J ¼ 7.2, 2H, Ar-H), 7.68 (dd, J ¼ 7.3, 7.4 Hz, 1H, Ar-H), 7.56–
1
.61 (m, 3H, Ar-H) ppm. C-NMR (125 MHz, DMSO-d ):
3
f
6
ꢀ
1
CHCl /MeOH, 96:4); Melting point: 123–125 C; H-NMR
(
d ¼ 195.11 (ketone carbonyl), 165.06 (amide carbonyl), 152.85
3
(
500 MHz, DMSO-d ): d ¼ 10.74 (s, 1H, NH amide), 8.77 (d,
(Ar-CH), 149.27 (Ar-CH), 143.51 (Ar-C Quaternary), 137.95 (Ar-
6
J ¼ 1.7 Hz, 1H, Ar-H), 8.70 (d, J ¼ 3.7 Hz, 1H, Ar-H), 7.98
C Quaternary), 136.10 (Ar-CH), 132.79 (Ar-CH), 132.49 (Ar-C
Quaternary), 131.46 (Ar-C Quaternary), 130.77 (2 Ar-CH),
(
(
7
7
d, J ¼ 7.9 Hz, 1H, Ar-H), 7.71 (d, J ¼ 7.9 Hz, 1H, Ar-H), 7.65
dd, J ¼ 7.3, 7.5 Hz, 1H, Ar-H), 7.59 (d, J ¼ 8.1 Hz, 2H, Ar-H);
1
(
1
29.89 (2 Ar-CH), 128.98 (2 Ar-CH), 124.01 (Ar-CH), 119.97
2 Ar-CH) ppm. IR (KBr disk): ꢀ ¼ 3309 (NH amide), 3101, 3039,
982, 1928, 1905, 1828, 1681 (ketone carbonyl), 1643 (amide
.46–7.50 (m, 2H, Ar-H), 7.36 (dd, J ¼ 7.5, 7.4 Hz, 1H, Ar-H),
13
.26 (d, J ¼ 7.9 Hz, 2H, Ar-H), 2.32 (s, 3H, CH3) ppm. C-NMR
ꢁ
1
(125 MHz, DMSO-d ): d ¼ 195.52 (ketone carbonyl), 164.41
carbonyl), 1589, 1519, 1450, 1411, 865, 740, 702 cm . HRMS
(
requires 301.09715).
6
+
ESI, negative mode): m/z [M-H ] 301.09594 (C H N O
(amide carbonyl), 152.68 (Ar-CH), 148.74 (Ar-CH), 143.48 (Ar-
C Quaternary), 136.57 (Ar-C Quaternary), 135.53 (Ar-CH),
19 13 2 2
1
35.05 (Ar-C Quaternary), 132.32 (Ar-CH), 132.20 (Ar-C
Quaternary), 130.65 (Ar-CH), 130.23 (Ar-C Quaternary), 130.18
2 Ar-CH), 129.22 (2 Ar-CH), 125.49 (Ar-CH), 125.15 (Ar-CH),
N-(2-benzoylphenyl)pyridine-3-carboxamide (C8). A mixture of
-amino-benzophenone (C7, 0.63 g, Mwt 197.24, 3.2 mmol) and
(
2
1
23.90 (Ar-CH), 21.56 (CH3) ppm. IR (KBr disk): ꢀ ¼ 3294 (NH
nicotinoyl chloride (C2, 0.50 gm, Mwt 141.56, 3.5 mmol) was
used to produce N-(2-benzoylphenyl)pyridine-3-carboxamide as
pale yellow solid (C8, 0.30 gm, Mwt 302.3, 31.0%). R : 0.62
amide), 3039, 2924, 2862, 1990, 1921, 1874, 1844, 1681 (ketone
carbonyl), 1620 (amide carbonyl), 1597, 1527, 1442, 933, 763,
f
ꢁ1
+
ꢀ
1
709 cm . HRMS (ESI, positive mode): m/z [M + Na ] 339.11038
C H N NaO requires 339.11040).
(
(
1
CHCl /MeOH, 96:4); Melting point: 133–136 C. H-NMR
3
(
2
0
16
2
2
500 MHz, DMSO-d ): d ¼ 10.74 (s, 1H, NH amide), 8.76 (m,
6
H, Ar-H), 8.70 (m, 1H, Ar-H), 7.98 (d, J ¼ 7.7, 1H, Ar-H), 7.65–
7
.71 (m, 4H, Ar-H), 7.56 (dd, J ¼ 6.8, 7.2 Hz, 1H, Ar-H), 7.52 (d, N-(2-benzoyl-4-chlorophenyl) pyridine-3-carboxamide (C14).
A
J ¼ 7.4 Hz, 1H, Ar-H); 7.47 (d, J ¼ 6.6 Hz, 3H, Ar-H), 7.38 (m, mixture of 2-amino-5-chlorobenzophenone (C13, 0.68 gm, Mwt
1
3
J ¼ 7, 7.2 Hz, 1H, Ar-H) ppm. C-NMR (125 MHz, DMSO-d ): 213.68, 3.2 mmol) and nicotinoyl chloride (C2, 0.50 gm, Mwt
6
d ¼ 195.80 (ketone carbonyl), 164.45 (amide carbonyl), 152.17 141.56, 3.5 mmol) was used to produce N-(2-benzoyl-4-chlor-
(
Ar-CH), 148.73 (Ar-CH), 137.70 (Ar-C Quaternary), 136.62 (Ar- ophenyl) pyridine-3-carboxamide as pale yellow solid (C14,
C Quaternary), 135.50 (Ar-CH), 133.05 (Ar-CH), 132.50 (Ar- 0.674 gm, Mwt 336.8, 62.5%). R : 0.73 (CHCl /MeOH, 96:4);
f
3
ꢀ
1
CH), 132.02 (Ar-C Quaternary), 130.74 (Ar-CH), 130.20 (Ar-C Melting point: 143–145 C. H-NMR (300 MHz, DMSO-d6):
Quaternary), 129.95 (2 Ar-CH), 128.66 (2 Ar-CH), 125.55 (Ar- d ¼ 10.71 (s, 1H, NH amide), 8.67 (m, 2H, Ar-H), 7.43–7.92 (m,
1
3
CH), 125.10 (Ar-CH), 123.90 (Ar-CH) ppm. IR (KBr disk): 10 H, Ar-H) ppm. C-NMR (300 MHz, DMSO-d ): d ¼ 193.38
6
ꢀ
¼ 3186 (NH amide), 3117, 3063, 1982, 1913, 1890, 1828, 1674 (ketone carbonyl), 164.06 (amide carbonyl), 152.30 (Ar-CH),