D. G. Daraji, K. D. Patel, H. D. Patel, and D. P. Rajani
Vol 000
ꢀ
1
ꢀ1
IR (KBr) λmax (cm ): 3287, 3068, 2896, 2767, 1676,
1
IR (KBr) λmax (cm ): 3276, 3095, 1618, 1572, 1474,
1
1
491, 1372, 1309, 1256, 1096, 961, 832, 728. H NMR
1318, 1248, 1029, 992, 860, 748, 689. H NMR
(
400 MHz, DMSO-d ): δ (ppm) = 10.107 (s, 1H, NH);
(400 MHz, DMSO-d ): δ (ppm) = 10.085 (s, 1H, NH);
6
6
7.651–7.504 (m, 4H, Ar); 7.499–7.482 (d, 2H, Ar,
7.680–6.869 (m, 8H, Ar); 4.689 (s, 2H, CH ); 3.714 (s,
2
J = 6.8); 6.894–6.871 (d, 2H, Ar, J = 9.2); 4.711 (s, 2H,
3H, CH ); 2.332 (s, 3H, COCH ); 2.087 (s, 3H, CH ).
Mass (m/z): 414.12 [M] .
2-((5-Acetyl-4-methyl-1-phenyl-1H-imidazol-2-yl)thio)-N-(4-
3
3
3
+
CH ); 3.715 (s, 3H, OCH ); 2.466 (s, 3H, COCH );
2
3
3
+
2
[
.343 (s, 3H, CH ). Mass (m/z): 429.7 [M] , 430.8
3
+
+
methoxyphenyl)acetamide (3k). Yield: 68%. MW:
395.47 g/mol. MF: C21H N O S; mp: 178.3°C. IR
21 3 3
M + 2] , 431.7 [M + 3] .
2
-((5-Acetyl-1-(4-chlorophenyl)-4-methyl-1H-imidazol-2-yl)
thio)-N-(4-bromophenyl)acetamide (3f). Yield: 85%. MW:
78.79 g/mol. MF: C H BrClN O S; mp: 192.6°C. IR
ꢀ
1
(KBr) λmax (cm ): 3278, 3062, 2840, 2774, 1674, 1504,
1
4
(
1372, 1307, 1252, 1178, 1073, 1029, 830, 699, 529. H
2
0
17
3 2
ꢀ
1
KBr) λmax (cm ): 3323, 3242, 3194, 3123, 3063, 2847,
NMR (400 MHz, DMSO-d
NH); 7.607–7.406 (m, 8H, Ar); 6.891–6.869 (t, 1H, Ar,
J = 8.8); 4.717 (s, 2H, CH ); 3.714 (s, 3H, OCH ); 2.466
(s, 3H, COCH ); 2.329 (s, 3H, CH ). Mass (m/z): 395.7
): δ (ppm) = 10.065 (s, 1H,
6
2
774, 1710, 1538, 1415, 1396, 1334, 1302, 1244, 1218,
1
1189, 1071, 967, 908, 831, 714, 681, 574. H NMR
2
3
(
400 MHz, DMSO-d ): δ (ppm) = 10.396 (s, 1H, NH);
3
3
6
+
+
7
.647–7.484 (m, 8H, Ar); 4.745 (s, 2H, CH ); 2.459 (s,
[M] , 396.6 [M + 1] .
2
1
3
2
-((5-Acetyl-1-(4-methoxyphenyl)-4-methyl-1H-imidazol-2-
3H, COCH ); 2.342 (s, 3H, CH ). C NMR (100 MHz,
3
3
yl)thio)-N-(4 methoxyphenyl)acetamide (3l).
Yield: 82%.
DMSO): δ (ppm) = 18.43, 29.53, 55.10, 114.98, 120.99,
MW: 425.50 g/mol. MF: C H N O S; mp: 143.4°C. IR
2
2 23 3 4
122.79, 123.33, 128.44, 129.44, 129.99, 131.61, 132.26,
ꢀ
1
(
KBr) λmax (cm ): 3288, 3063, 2840, 2782, 1684, 1503,
1523, 1345, 1243, 1156, 1034, 846, 713, 521. H NMR
1
38.03, 143.06, 156.92, 166.49, 169.73, 188.93. Mass
1
+
(
m/z): 479.6 [M + 1] .
(
400 MHz, DMSO-d ): δ (ppm) = 10.047 (s, 1H, NH);
2
-((5-Acetyl-1-(4-chloropenyl)-4-methyl-1H-imidazol-2-yl)
6
thio)-N-(benzo[d]thiazol-2-yl)acetamide (3g).
Yield: 25%.
7.528–6.868 (m, 8H, Ar); 4.661 (s, 2H, CH
3H, OCH ); 3.714 (s, 3H, OCH ); 2.459 (s, 3H, COCH
2.312 (s, 3H, CH ). Mass (m/z): 425.7 [M] , 426.7 [M + 1] .
); 3.793 (s,
2
MW: 456.97 g/mol. MF: C H ClN O S ; mp: 115.8°C.
3
3
3
);
2
1
17
4 2 2
ꢀ
1
+
+
IR (KBr) λmax (cm ): 3189, 3066, 2992, 2770, 1709,
3
2
-((5-Acetyl-4-methyl-1-(4-nitrophenyl)-1H-imidazol-2-yl)
1
651, 1608, 1548, 1490, 1370, 1320, 1268, 1182, 1019,
1
thio)-N-(4-methoxyphenyl)acetamide (3m).
Yield: 74%.
972, 837, 757, 642, 511. H NMR (400 MHz,
MW: 440.47 g/mol. MF: C H N O S; mp: 172.4°C. IR
2
1 20 4 5
DMSO-d ): δ (ppm) = 7.971 (s, 1H, NH); 7.770–7.293
6
ꢀ
1
(
KBr) λmax (cm ): 3286, 3158, 2965, 1784, 1669, 1557,
(
2
m, 8H, Ar); 4.918 (s, 2H, CH ); 2.447 (s, 3H, COCH );
2 3
+
1494, 1327, 1325, 1248, 1204, 1102, 1025, 867, 787, 640,
.346 (s, 3H, CH ). Mass (m/z): 456.5 [M] .
3
1
5
76. H NMR (400 MHz, DMSO-d ): δ (ppm) = 10.028
6
2
-((5-Acetyl-1-(4-chlorophenyl)-4-methyl-1H-imidazol-2-yl)
(s, 1H, NH); 7.878–6.867 (m, 8H, Ar); 4.655 (s, 2H,
thio)-N-(4-nitrophenyl)acetamide (3h).
Yield: 59%. MW:
CH ); 3.780 (s, 3H, OCH ); 2.686 (s, 3H, COCH ); 2.312
4
44.89 g/mol. MF: C H ClN O S; mp: 216.4°C. IR
2
3
3
2
0
17
4 4
+
+
ꢀ
1
(
s, 3H, CH ). Mass (m/z): 440.08 [M] , 441.08 [M + 1] .
In vitro activity. In vitro antimicrobial activity of all
(KBr) λmax (cm ): 3288, 3158, 3098, 2950, 1714, 1609,
3
1
6
555, 1413, 1371, 1257, 1204, 1185, 1015, 848, 745,
1
synthesized novel substituted 2-((5-acetyl-4-methyl-1-
phenyl-1H-imidazole-2-yl)thio)-N-phenylacetamide
40, 576.
H
NMR (400 MHz, DMSO-d6):
δ
(ppm) = 10.896 (s, 1H, NH); 8.248–8.225 (d, 2H, Ar,
derivatives were checked against Staphylococcus aureus,
Escherichia coli, Streptococcus pyogenes, Pseudomonas
aeruginosa strains of antibacterial and Candida
albicans, Aspergillus niger, Aspergillus clavatus strains
of antifungal by using a method as described by S. M.
Prajapati [18]. In vitro antituberculosis activity of all
the synthesized derivatives against mycobacterium
tuberculosis H37Rv strain was tested by utilizing
Lowenstein–Jensen medium (conventional method) as
J = 9.2); 7.854–7.831 (d, 2H, Ar, J = 9.2); 7.657–7.588
(
2
m, 4H, Ar); 4.820 (s, 2H, CH ); 2.456 (s, 3H, COCH );
.345 (s, 3H, CH3). C NMR (100 MHz, DMSO): δ
2 3
1
3
(ppm) = 18.41, 29.51, 29.70, 55.20, 118.81, 122.79,
1
1
23.43, 125.05, 128.41, 129.44, 130.03, 132.33, 142.30,
42.99, 144.76, 156.87, 167.47, 169.62, 188.98. Mass
+
+
(
m/z): 444.5 [M] , 446.5 [M + 2] .
2
-((5-Acetyl-1-(4-chlorophenyl)-4-methyl-1H-imidazol-2-yl)
thio)-N-(pyridin-2-yl)acetamide (3i).
Yield: 66%. MW:
4
00.88 g/mol. MF: C H ClN O S; mp: 78.6°C. IR (KBr)
described by A. Rattan [19].
Docking methodology. Maestro 10.7 was used to carry
1
9
17
4 2
ꢀ
1
λmax (cm ): 3277, 3197, 3083, 1608, 1515, 1403, 1373,
1
out molecular docking study using default settings.
Protein transferase (PDB ID: 1HNJ) [20] and antibiotic
resistance (PDB ID: 1W3R) [21] were employed from
the protein data bank with the incorporated ligand
structure in binding site [22]. Proteins were prepared in
“protein preparation wizard” tool fused in Glide using
default settings. All the ligands were prepared using
1236, 1174, 1086, 1030, 822, 706. H NMR (400 MHz,
DMSO-d ): δ (ppm) = 10.804 (s, 1H, NH); 8.339–6.974
6
(m, 8H, Ar); 4.814 (s, 2H, CH ); 2.437 (s, 3H, COCH );
2
3
+
2.359 (s, 3H, CH ). Mass (m/z): 401.08 [M + 1] .
3
2
-((5-Acetyl-1-(4-fluorophenyl)-4-methyl-1H-imidazol-2-yl)
thio)-N-(4-methoxyphenyl)acetamide (3j).
MW: 413.47 g/mol. MF: C H FN O S; mp: 171.6°C.
Yield: 70%.
2
1
20
3 3
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet