Arylazolyl(azinyl)thioacetanilides
134.31, 132.45, 132.31, 131.14, 129.55, 128.37, 128.22,
127.87, 127.60, 127.33, 125.69, 124.57, 123.42, 122.70,
118.53, 117.91, 115.75, 36.62 (CH-S), 13.43 (cyclopropyl-
C), 7.77 (cyclopropyl-C), 7.69 (cyclopropyl-C). ESI-MS: m/
ppm) d: 10.29 (s, 1H, NH), 8.62 (d, 1H, J = 8.00 Hz,
pyridylimidazole-H), 8.44 (d, 1H, J = 8.00 Hz, naphthaline-
H), 8.30 (d, 1H, J = 8.00 Hz, pyridine-H), 8.20 (d, 1H,
J = 4.00 Hz, pyridylimidazole-H), 7.72–7.70 (m, 2H, naph-
thaline-H), 7.53 (t, 1H, J = 8.00 Hz, pyridylimidazole-H),
7.48 (d, 1H, J = 4.00 Hz, pyridine-H), 7.45 (dd, 1H,
J1 = 8.00 Hz, J2 = 4.00 Hz, naphthaline-H), 7.30 (d, 1H,
J = 8.00 Hz, naphthaline-H), 7.17 (dd, 1H, J1 = 8.00 Hz,
J2 = 4.00 Hz, pyridine-H), 7.12 (d, 1H, J = 8.00 Hz, naph-
thaline-H), 4.47–4.38 (m, 2H, S-CH2), 2.62–2.55 (m, 1H,
cyclopropyl-H), 1.18–1.15 (m, 2H, cyclopropyl-H), 0.91–
0.87 (m, 2H, cyclopropyl-H). 13C-NMR (100 MHz, DMSO-
d6, ppm) d: 167.40 (C=O), 156.95, 155.69, 145.63,
144.45, 142.96, 134.31, 133.09, 132.32, 131.10, 129.44,
128.38, 128.22, 127.60, 127.32, 125.69, 123.93 (2 9 C),
123.41, 122.69, 118.54, 117.90, 36.56 (S-C), 13.43 (cy-
clopropyl-C), 7.77 (cyclopropyl-C), 7.69 (cyclopropyl-C).
ESI-MS: m/z 486.4 (M + 1), 489.4 (M + 3), 508.3
(M + 23). C26H20ClN5OS [485.11].
z
572.3 (M + 1), 574.4 (M + 3), 594.4 (M + 23).
C
28H22BrN5O2S [571.07].
3-Chloro-4-(2-(1-(4-cyclopropylnaphthalen-1-yl)-1H-
imidazo[4,5-b]pyridin-2-ylthio)acetamido)benzoic acid
(14). White powder, yield: 28.6%. mp: 224–225 °C. 1H
NMR (400 MHz, DMSO-d6, ppm) d: 13.13 (s, 1H, COOH),
11.34 (s, 1H, NH), 8.62 (d, 1H, J = 8.00 Hz, pyridylimida-
zole-H), 8.44 (d, 1H, J = 8.00 Hz, naphthaline-H), 8.17 (d,
1H, J = 8.00 Hz, pyridylimidazole-H), 7.96 (s, 1H, PhH),
7.90 (d, 1H, J = 12.00 Hz, naphthaline-H), 7.72–7.71 (m,
2H, naphthaline-H), 7.55 (t, 1H, J = 8.00 Hz, pyridylimida-
zole-H), 7.48 (d, 1H, J = 8.00 Hz, PhH), 7.30 (d, 1H,
J = 8.00 Hz, naphthaline-H), 7.18–7.14 (m, 1H, PhH), 7.11
(d, 1H, J = 8.00 Hz, naphthaline-H), 4.48–4.38 (m, 2H, S-
CH2), 2.62–2.55 (m, 1H, cyclopropyl-H), 1.19–1.16 (m, 2H,
cyclopropyl-H), 0.90-0.88 (m, 2H, cyclopropyl-H). 13C-NMR
(100 MHz, DMSO-d6, ppm) d: 167.34 (C=O), 166.24 (C=O),
156.89, 155.63, 144.49, 142.98, 139.17, 134.31, 131.13,
130.71, 129.53, 129.21, 128.34, 128.24, 128.12, 127.61,
127.34, 125.69, 124.47, 123.41 (2 9 C), 122.66, 118.58,
117.94, 36.56 (S-C), 13.43 (cyclopropyl-C), 7.77 (cyclo-
propyl-C), 7.69 (cyclopropyl-C). ESI-MS: m/z 529.3 (M + 1),
531.2 (M + 3), 551.3 (M + 23). C28H21ClN4O3S [528.1].
3-Chloro-4-(2-(1-(4-cyclopropylnaphthalen-1-yl)-1H-
imidazo[4,5-b]pyridin-2-ylthio)acetamido)-N-
methoxybenzamide (17). White powder, yield: 41.1%.
mp: 160–161 °C. 1H NMR (400 MHz, DMSO-d6, ppm) d:
11.83 (s, 1H, CONH), 10.29 (s, 1H, NH), 8.62 (d, 1H,
J = 8.00 Hz,
pyridylimidazole-H),
8.44
(d,
1H,
J = 8.00 Hz, naphthaline-H), 8.09 (d, 1H, J = 8.00 Hz,
pyridylimidazole-H), 7.85 (s, 1H, PhH), 7.72–7.55 (m, 3H,
naphthaline-H), 7.53 (t, 1H, J = 8.00 Hz, pyridylimidazole-
H), 7.48 (d, 1H, J = 8.00 Hz, PhH), 7.30 (d, 1H,
J = 8.00 Hz, naphthaline-H), 7.17 (m, 1H, PhH), 7.11 (d,
1H, J = 8.00 Hz, naphthaline-H), 4.48–4.38 (m, 2H, S-
CH2), 3.70 (s, 3H, N-CH3), 2.62–2.55 (m, 1H, cyclo-
propyl-H), 1.19–1.16 (m, 2H, cyclopropyl-H), 0.90–0.88
(m, 2H, cyclopropyl-H). 13C-NMR (100 MHz, DMSO-d6,
ppm) d: 170.27 (C=O), 166.69 (C=O), 156.46, 155.15,
143.96, 142.46, 137.57, 133.80, 130.61, 129.11, 129.02,
128.10, 127.85, 127.71, 127.09, 126.81, 126.41, 125.18,
124.33, 123.29, 122.88, 122.15, 118.04, 117.40, 63.29
(O-CH), 36.11 (S-CH), 12.91 (cyclopropyl-C), 7.25 (cyclo-
propyl-C), 7.18 (cyclopropyl-C). ESI-MS: m/z 588.3
(M + 1), 560.3 (M + 3), 580.3 (M + 23). C29H24ClN5O3S
[557.13].
Ethyl3-chloro-4-(2-(1-(4-cyclopropylnaphthalen-1-yl)-
1H-imidazo[4,5-b]pyridin-2-ylthio)acetamido)benzoate
(15). White powder, yield: 42.5%. mp: 141–142 °C. 1H
NMR (400 MHz, DMSO-d6, ppm) d: 10.36 (s, 1H, NH),
8.62 (d, 1H, J = 8.00 Hz, pyridylimidazole-H), 8.44 (d, 1H,
J = 4.00 Hz, naphthaline-H), 8.21 (d, 1H, J = 8.00 Hz,
pyridylimidazole-H), 7.98 (s, 1H, PhH), 7.92 (d, 1H,
J = 8.00 Hz, naphthaline-H), 7.72–7.70 (m, 2H, naphtha-
line-H), 7.53(t, 1H, J = 8.00 Hz, pyridylimidazole-H), 7.48
(d, 1H, J = 8.00 Hz, PhH), 7.31 (d, 1H, J = 8.00 Hz,
naphthaline-H), 7.17 (dd, 1H, J1 = 8.00 Hz, J2 = 4.00 Hz,
naphthaline-H), 7.11 (d, 1H, J = 8.00 Hz, PhH), 4.49–4.39
(m, 2H, S-CH2), 4.33 (q, 2H, J = 4.00 Hz, CH2), 2.62–
2.55 (m, 1H, cyclopropyl-H), 1.33 (t, 3H, J = 4.00 Hz,
CH3), 1.20–1.15 (m, 2H, cyclopropyl-H), 0.91–0.87 (m,
2H, cyclopropyl-H). 13C-NMR (100 MHz, DMSO-d6, ppm)
d: 167.20 (C=O), 164.69 (C=O), 156.98, 155.63, 144.49,
142.98, 139.53, 134.31, 131.13, 130.53, 129.53, 129.07,
128.34, 128.24, 127.61, 127.33, 127.02, 125.69, 124.49,
123.40 (2 9 C), 122.66, 118.58, 117.95, 61.63 (CH2-O),
36.37 (S-C), 14.58 (CH3), 13.43 (cyclopropyl-C), 7.77 (cy-
clopropyl-C), 7.69 (cyclopropyl-C). ESI-MS: m/z 557.2
(M + 1), 559.3 (M + 3), 579.4 (M + 23). C30H25ClN4O3S
[556.13].
Ethyl2-(3-chloro-4-(2-(1-(4-cyclopropylnaphthalen-1-
yl)-1H-imidazo[4,5-b]pyridin-2-ylthio)acetamido)
benzamido)acetate (18). White powder, yield: 44.2%.
mp: 221–222 °C. 1H NMR (400 MHz, DMSO-d6, ppm) d:
10.27 (s, 1H, NH), 9.03 (t, 1H, J = 8.00 Hz, NH), 8.62 (d,
1H, J = 8.00 Hz, pyridylimidazole-H), 8.44 (d, 1H,
J = 4.00 Hz, naphthaline-H), 8.11 (d, 1H, J = 12.00 Hz,
pyridylimidazole-H), 7.99 (s, 1H, PhH), 7.85 (d, 1H,
J = 12.00 Hz, naphthaline-H), 7.72–7.70 (m, 2H, naphtha-
line-H), 7.55 (t, 1H, J = 8.00 Hz, pyridylimidazole-H), 7.49
(d, 1H, J = 12.00 Hz, PhH), 7.31 (d, 1H, J = 16.00 Hz,
naphthaline-H), 7.17 (dd, 1H, J1 = 12.00 Hz, J2 = 8.0 Hz,
naphthaline-H), 7.12 (d, 1H, J = 8.00 Hz, PhH), 4.49–4.37
(m, 2H, S-CH2), 4.16 (q, 2H, J = 8.00 Hz, CH2),
N-(2-Chloropyridin-3-yl)-2-(1-(4-
cyclopropylnaphthalen-1-yl)-1H-imidazo[4,5-b]
pyridin-2-ylthio)acetamide (16). White powder, yield:
40.1%. mp: 204–205 °C. 1H NMR (400 MHz, DMSO-d6,
Chem Biol Drug Des 2016; 88: 241–253
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