T.H. Al-Tel et al. / European Journal of Medicinal Chemistry 46 (2011) 1874e1881
1879
2H), 7.21 (d, J ¼ 7.4 Hz, 1H). 13C NMR (75 MHz, CDCl3, in ppm):
154.1,152.3, 147.4,139.1, 137.5, 136.2, 134.3, 132.6, 130.4, 129.2, 127.9,
126.1, 125.7, 124.3, 120.5, 119.6, 119.2, 115.4, 113.2, 110.3, 98.7. HRMS
(ESI): calcd. for C29H17BrFN7O3 [M þ Na]þ: 632.04579; found
632.04570.
d
149.3, 147.5, 140.9, 134.3, 132.4, 130.7, 129.6, 127.8, 125.6, 124.5,
122.3, 121.8, 120.4, 119.2, 118.7, 118.1, 115.5, 113.3, 112.6, 98.4. HRMS
(ESI): calcd. for C30H19BrFN7O2 [M þ Na]þ: 630.06653; found
630.06662.
4.2.12. 2-(6-Bromoquinolin-3-yl)-N-(4-fluorophenyl)-6-(6-methyl-
1H-benzo[d]imidazol-2-yl)imidazo[1,2-a]pyridin-3-amine (10a)
This derivative was synthesized according to the general
experimental procedure B. Yield 73%, white solid, m.p. 207e208 ꢁC.
4.2.7. 2-(5-Bromo-1H-indol-3-yl)-N-(4-fluorophenyl)-6-(5-p-tolyl-
1H-imidazol-2-yl)imidazo[1,2-a]pyridin-3-amine (6b)
This derivative was synthesized according to the general
experimental procedure C. Yield 56%, white solid, m.p. 199e200 ꢁC.
1H NMR (300 MHz, CDCl3, in ppm):
d 10.58 (s, 1H), 9.17 (d,
1H NMR (300 MHz, CDCl3, in ppm):
d
10.31 (s, 1H), 9.39 (bs, 1H),
J ¼ 8.4 Hz, 1H), 8.75 (s, 1H), 8.49 (s, 1H), 8.42 (s, 1H), 8.23 (d,
J ¼ 8.1 Hz, 2H), 7.94 (dd, J ¼ 7.1, 8.4 Hz, 2H), 7.79 (d, J ¼ 1.4 Hz, 1H),
7.74 (bs, 1H), 7.39 (m, 4H), 7.21 (bs, 1H), 7.09 (d, J ¼ 6.9 Hz, 1H), 2.49
8.52 (d, J ¼ 1.4 Hz, 1H), 8.25 (dd, J ¼ 3.5, 9.8 Hz, 2H), 8.11 (bs, 2H),
7.95 (s, 1H), 7.45e7.34 (m, 6H), 7.19 (d, J ¼ 7.3 Hz, 1H), 2.49 (s, 3H).
13C NMR (75 MHz, CDCl3, in ppm):
d
148.6, 147.4, 137.5, 134.8, 132.1,
(s, 3H).13C NMR (75 MHz, CDCl3, in ppm):
d 160.2, 151.1, 149.5, 145.9,
131.9,130.4,128.7,128.3,125.6,124.1,122.9,122.3,120.4,119.3,115.7,
113.2, 112.5, 98.7, 22.4. HRMS (ESI): calcd. for C31H22BrFN6
[M þ Na]þ: 599.09710; found 599.09717.
145.3,144.4,143.1,136.7,135.8,134.2,131.3,129.7,128.5,126.1,124.5,
121.3, 120.6, 120.2, 118.4, 117.1, 22.3. HRMS (ESI): calcd. for
C30H20BrFN6 [M þ Na]þ: 585.08145; found 585.08153.
4.2.8. 2-(5-Bromo-1H-indol-3-yl)-N-(4-fluorophenyl)-6-(5-(4-
fluorophenyl)-1H-imidazol-2-yl)imidazo[1,2-a]pyridin-3-amine
(6c)
4.2.13. 2-(6-Bromoquinolin-3-yl)-6-(6-fluoro-1H-benzo[d]
imidazol-2-yl)-N-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-amine
(10b)
This derivative was synthesized according to the general
This derivative was synthesized according to the general
experimental procedure C. Yield 69%, white solid, m.p. 203e204 ꢁC.
experimental procedure B. Yield 65%, white solid, m.p. 215e216 ꢁC.
1H NMR (300 MHz, CDCl3, in ppm):
d
9.89 (s, 1H), 9.32 (bs, 1H), 8.64
1H NMR (300 MHz, CDCl3, in ppm):
d 10.49 (s, 1H), 9.21 (s, 1H), 8.97
(d, J ¼ 1.5 Hz,1H), 8.36 (d, J ¼ 9.1 Hz, 2H), 8.08 (d, J ¼ 7.1 Hz,1H), 7.85
(s, 1H), 7.64 (s, 1H), 7.41 (dd, J ¼ 1.6, 7.2 Hz, 1H), 7.39 (d, J ¼ 7.9 Hz,
2H), 7.22 (s, 1H), 7.13 (dd, J ¼ 1.7, 7.2 Hz, 2H), 7.03 (dd, J ¼ 1.4, 8.1 Hz,
(s, 1H), 8.77 (s, 1H), 8.59 (d, J ¼ 8.7 Hz, 1H), 8.39 (d, J ¼ 8.2 Hz, 1H),
8.14 (dd, J ¼ 7.2, 8.3 Hz, 2H), 7.89e7.71 (m, 3H), 7.46 (d, J ¼ 8.4 Hz,
2H), 7.31 (dd, J ¼ 1.5, 5.6 Hz, 1H), 7.13 (d, J ¼ 7.1 Hz, 1H). 13C NMR
1H). 13C NMR (75 MHz, CDCl3, in ppm):
d
163.6, 159.1, 148.4, 147.2,
(75 MHz, CDCl3, in ppm): d 159.8, 151.4, 149.5, 145.9, 145.3, 140.6,
140.7, 134.5, 132.3, 130.2, 128.4, 126.5, 125.7, 125.4, 122.6, 120.3,
119.6, 118.5, 115.3, 115.1, 113.2, 112.9, 97.9. HRMS (ESI): calcd. for
C30H19BrF2N6 [M þ Na]þ: 603.07203; found 603.07211.
137.3, 136.4, 134.5, 131.2, 130.7, 129.8, 128.5, 125.2, 124.8, 122.5,
120.7, 120.3, 118.6, 111.5, 110.9, 106.1, 105.8. HRMS (ESI): calcd. for
C29H17BrF2N6 [M þ Na]þ: 589.05638; found 589.05645.
4.2.9. 2-(5-Bromo-1H-indol-3-yl)-N-(4-fluorophenyl)-6-(5-(4-
fluorophenyl)-1,3,4-oxadiazol-2-yl)imidazo[1,2-a]pyridin-3-amine
(7a)
4.2.14. 2-(6-Bromoquinolin-3-yl)-N-(4-fluorophenyl)-6-(6-nitro-
1H-benzo[d]imidazol-2-yl)imidazo[1,2-a]pyridin-3-amine (10c)
This derivative was synthesized according to the general
experimental procedure B. Yield 53%, white solid, m.p. 205e206 ꢁC.
This derivative was synthesized according to the general
procedure D. Yield 55%, white solid, m.p. 189e190 ꢁC. 1H NMR
1H NMR (300 MHz, CDCl3, in ppm):
d
10.81 (s,1H), 9.17 (d, J ¼ 7.0 Hz,
(300 MHz, CDCl3, in ppm):
d
9.29 (s, 1H), 8.59 (s, 1H), 8.24 (d,
1H), 8.96 (s, 1H), 8.73 (d, J ¼ 2.7 Hz, 1H), 8.37 (d, J ¼ 8.4 Hz, 1H), 8.09
(bs, 1H), 7.94 (dd, J ¼ 7.1, 8.3 Hz, 2H), 7.78e7.73 (m, 3H), 7.52 (d,
J ¼ 5.6 Hz, 1H), 7.39 (d, J ¼ 8.3 Hz, 2H), 7.17 (d, J ¼ 7.4 Hz, 1H). 13C
J ¼ 7.3 Hz, 2H), 7.89 (s,1H), 7.75 (d, J ¼ 5.3 Hz, 2H), 7.63 (d, J ¼ 5.9 Hz,
2H), 7.44 (m, 2H), 7.40 (d, J ¼ 1.5 Hz, 1H), 7.38 (m, 3H), 7.13 (dd,
J ¼ 1.7, 5.9 Hz, 1H). 13C NMR (75 MHz, CDCl3, in ppm):
d
167.4, 163.7,
NMR (75 MHz, CDCl3, in ppm): d 159.7, 151.5, 150.3, 145.2, 141.4,
157.6, 154.8, 147.4, 134.8, 132.3, 130.4, 128.7, 126.5, 125.9, 125.3,
124.8, 120.4, 119.7, 119.1, 115.6, 115.3, 114.5, 113.2, 110.1, 98.2. HRMS
(ESI): calcd. for C29H17BrF2N6O [M þ Na]þ: 605.05130; found
605.05123.
137.6,136.5, 134.3,131.4,130.1,129.2,126.7,122.4,120.8,120.2,119.7,
117.9, 116.5, 108.1. HRMS (ESI): calcd. for C29H17BrFN7O2 [M þ Na]þ:
616.05088; found 616.05079.
4.2.15. 2-(6-Bromoquinolin-3-yl)-N-(4-fluorophenyl)-6-(5-(4-
fluorophenyl)-1H-imidazol-2-yl)imidazo[1,2-a]pyridin-3-amine
(11a)
4.2.10. 2-(5-Bromo-1H-indol-3-yl)-N-(4-fluorophenyl)-6-(5-p-
tolyl-1,3,4-oxadiazol-2-yl)imidazo[1,2-a]pyridin-3-amine (7b)
This derivative was synthesized according to the general
experimental procedure D. Yield 67%, white solid, m.p. 202e203 ꢁC.
This derivative was synthesized according to the general
experimental procedure C. Yield 59%, white solid, m.p. 195e196 ꢁC.
1H NMR (300 MHz, CDCl3, in ppm):
d
9.31 (s, 1H), 8.61 (s, 1H), 8.15
1H NMR (300 MHz, CDCl3, in ppm):
d
10.54 (s, 1H), 9.28 (dd, J ¼ 0.9,
(m, 4H), 7.56e7.45 (m, 7H), 7.34 (d, J ¼ 7.1 Hz, 1H), 2.47 (s, 3H). 13C
9.7 Hz, 1H), 8.92 (s,1H), 8.49 (m, 2H), 8.28 (d, J ¼ 8.3 Hz, 1H), 8.14 (d,
J ¼ 8.7 Hz, 2H), 7.92 (dd, J ¼ 7.2, 8.5 Hz, 2H), 7.79 (m, 2H), 7.45 (bs,
1H), 7.37 (m, 2H), 7.18 (d, J ¼ 4.5 Hz, 2H), 7.03 (d, J ¼ 7.6 Hz, 1H). 13C
NMR (75 MHz, CDCl3, in ppm):
d 158.1, 154.3, 147.5, 138.7, 137.6,
134.4, 132.5, 130.8, 129.1, 127.5, 127.3, 125.6, 124.9, 124.4, 120.7,
120.3, 119.1, 114.8, 112.7, 109.9, 97.6, 22.1. HRMS (ESI): calcd. for
C30H20BrFN6O [M þ Na]þ: 601.07637; found 601.07629.
NMR (75 MHz, CDCl3, in ppm):
d 163.2, 159.5, 151.3, 148.6, 147.4,
145.8, 141.3, 136.7, 134.5, 131.3, 130.2, 127.6, 126.4, 125.9, 123.7,
120.8, 120.1, 119.6, 119.2, 115.4, 114.3. HRMS (ESI): calcd. for
C31H19BrF2N6 [M þ Na]þ: 615.07203; found 615.07213.
4.2.11. 2-(5-Bromo-1H-indol-3-yl)-N-(4-fluorophenyl)-6-(5-(4-
nitrophenyl)-1,3,4-oxadiazol-2-yl)imidazo[1,2-a]pyridin-3-amine
(7c)
4.2.16. 2-(6-Bromoquinolin-3-yl)-N-(4-fluorophenyl)-6-(5-p-tolyl-
1H-imidazol-2-yl)imidazo[1,2-a]pyridin-3-amine (11b)
This derivative was synthesized according to the general
experimental procedure D. Yield 71%, white solid, m.p. 213e214 ꢁC.
This derivative was synthesized according to the general
1H NMR (300 MHz, CDCl3, in ppm):
d 9.27 (s, 1H), 8.56 (s, 1H), 8.42
experimental procedure C. Yield 72%, white solid, m.p. 196e197 ꢁC.
(m, 4H), 8.20 (d, J ¼ 7.3 Hz, 2H), 7.94 (bs, 1H), 7.49e7.38 (m, 5H),
1H NMR (300 MHz, CDCl3, in ppm):
1H), 9.08 (s, 1H), 8.81 (bs, 1H), 8.49 (m, 2H), 8.31 (d, J ¼ 8.1 Hz, 1H),
d
10.19 (s,1H), 9.15 (d, J ¼ 8.3 Hz,
6.97 (d, J ¼ 7.2 Hz, 1H). 13C NMR (75 MHz, CDCl3, in ppm):
d 158.5,