Med Chem Res (2013) 22:165–174
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Ar–H), 7.86 (t, J = 7.80 Hz, 1H, Ar–H), 8.10 (d,
J = 7.80 Hz, 1H, Ar–H), 8.24 (d, J = 7.80 Hz, 1H, Ar–H),
8.55 (s, 1H, Ar–H); HRMS (ESI?) calcd for C32H30N4O2
[M ? Na]?: 434.1844; found: 434.1821.
Ar–H), 7.76 (t, J = 7.34 Hz, 1H, Ar–H), 7.90 (t,
J = 7.34 Hz, 1H, Ar–H), 8.01 (s, 1H, NH), 8.15 (d,
J = 7.34 Hz, 1H, Ar–H), 8.25 (d, J = 8.39 Hz, 1H, Ar–
H), 8.62 (s, 1H, Ar–H); HRMS (ESI?) calcd for
C32H30N4O2 [M ? Na]?: 424.1637; found: 424.1609.
(E)-N-{3-[4-(2-oxo-2-(piperidin-1-yl)ethyl)phenyl]allyl}-
1H-pyrrolo[3,4-b] quinolin-3(2H)-one (1f)
Synthesis of N-{3-[4-(2-oxo-2-(4-phenylpiperidin-1-
yl)ethyl)phenyl]propyl}-1H-pyrrolo[3,4-b]quinolin-3(2H)-
one (2a)
The general synthetic method described above afforded 1f
as off white solid. Yield 70 %, mp 144–147 °C. IR (KBr, v
cm-1): 2931, 2853, 1687, 1628, 1383, 1166, 1129, 1021,
970, 768; 1H NMR (400 MHz, DMSO-d6): d 1.23–1.44 (m,
4H, 2 9 CH2), 1.45–1.69 (m, 4H, 2 9 CH2), 2.97–3.08
(m, 2H, CH2), 3.66 (s, 2H, CH2), 4.43 (d, J = 5.85 Hz, 2H,
CH2), 4.68 (s, 2H, CH2), 6.32–6.44 (m, 1H, =CH), 6.65 (d,
J = 15.29 Hz, 1H, =CH), 7.18 (d, J = 8.12 Hz, 2H, Ar–
H), 7.41 (d, J = 8.12 Hz, 2H, Ar–H), 7.73 (t, J = 7.38 Hz,
1H, Ar–H), 7.86 (t, J = 7.65 Hz, 1H, Ar–H), 8.12 (d,
J = 8.30 Hz, 1H, Ar–H), 8.21 (d, J = 8.49 Hz, 1H, Ar–
H), 8.49 (s, 1H, Ar–H); HRMS (ESI?) calcd for
C32H30N4O2 [M ? Na]?: 448.2001; found: 448.1981.
The general synthetic method described above afforded 2a as
brownish solid. Yield 76 %, mp 162–164 °C. IR (KBr, v
cm-1): 3052, 2934, 2810, 1695, 1643, 1464, 1382, 1234,
1
1153, 1035, 968. 754; H NMR (300 MHz, DMSO-d6): d
2.00 (m, 2H, CH2), 2.65 (t, J = 7.56 Hz, 2H, CH2), 2.95–
3.12 (m, 4H, 2 9 CH2), 3.54–3.73 (m, 8H, 4 9 CH2), 4.62
(s, 2H, CH2), 6.76 (t, J = 7.26 Hz, 1H, Ar–H), 6.87 (d,
J = 7.93 Hz, 2H, Ar–H), 7.09–7.23 (m, 6H, Ar–H), 7.68 (t,
J = 7.65 Hz, 1H, Ar–H), 7.82 (t, J = 7.55 Hz, 1H, Ar–H),
8.07 (d, J = 7.93 Hz, 1H, Ar–H), 8.19 (d, J = 9.06 Hz, 1H,
Ar–H), 8.51 (s, 1H, Ar–H); HRMS (ESI?) calcd for
C32H30N4O2 [M ? Na]?: 527.2423; found: 527.2400.
Synthesis of (E)-N,N-diisopropyl-N-{4-[3-(3-oxo-1H-
pyrrolo[3,4-b]quinolin-2(3H)-yl)prop-1-enyl]
phenyl}acetamide (1g)
Synthesis of N-{3-[4-(2-(4-(4-methoxyphenyl)piperidin-1-
yl)-2-oxoethyl) phenyl] propyl}-1H-pyrrolo[3,4-b]
quinolin-3(2H)-one (2b)
The general synthetic method described above afforded 1g
as off white solid. Yield 75 %, mp 194–196 °C. IR (KBr, v
cm-1): 2964, 2928, 1689, 1640, 1465, 1330, 1241, 1126,
1043, 990, 753; 1H NMR (300 MHz, DMSO-d6): d 0.95 (d,
J = 6.61 Hz, 3H, CH3), 1.20 (d, J = 6.42 Hz, 3H, CH3),
1.28 (d, J = 6.61 Hz, 6H, 2 9 CH3), 3.62 (s, 2H, CH2),
3.91–4.05 (m, 2H, 2 9 CH), 4.43 (d, J = 5.85 Hz, 2H,
CH2), 4.68 (s, 2H, CH2), 6.32–6.45 (m, 1H, CH), 6.64 (d,
J = 15.67 Hz, 1H, =CH), 7.17 (d, J = 8.12 Hz, 2H, Ar–
H), 7.42 (d, J = 8.12 Hz, 2H, Ar–H); 7.73 (t, J = 7.08 Hz,
1H, Ar–H); 7.86 (t, J = 7.08 Hz, 1H, Ar–H), 8.13 (d,
J = 8.30 Hz, 1H, Ar–H), 8.26 (d, J = 8.49 Hz, 1H, Ar–
H), 8.60 (s, 1H, Ar–H); HRMS (ESI?) calcd for
C32H30N4O2 [M ? Na]?: 464.2314; found: 464.2292.
The general synthetic method described above afforded 2b
as white solid. Yield 80 %, mp 178–180 °C. IR (KBr, v
cm-1): 2924, 2821, 1689, 1632, 1512, 1383, 1249, 1157,
1036, 973, 909, 784; 1H NMR (300 MHz, DMSO-d6): d 1.98
(m, 2H, CH2), 2.62 (t, J = 7.36 Hz, 2H, CH2), 2.82–2.98 (m,
4H, 2 9 CH2), 3.53–3.73 (m, 9H, 3 9 CH3, OCH3), 4.64 (s,
2H, CH2), 6.80 (d, J = 8.87 Hz, 2H, Ar–H), 6.88 (d,
J = 8.87 Hz, 2H, Ar–H), 7.15 (d, J = 8.12 Hz, 2H, Ar–H),
7.20 (d, J = 7.93 Hz, 2H, Ar–H), 7.72 (t, J = 7.82 Hz, 1H,
Ar–H), 7.86 (t, J = 7.55 Hz, 1H, Ar–H), 8.12 (d,
J = 7.93 Hz, 1H, Ar–H), 8.20 (d, J = 7.93 Hz, 1H, Ar–H),
8.58 (s, 1H, Ar–H); HRMS (ESI?) calcd for C32H30N4O2
[M ? Na]?: 557.2529; found: 557.2506.
Synthesis of (E)-N-(2-hydroxyethyl)-N-{4-[3-(3-oxo-1H-
pyrrolo[3,4-b]quinolin-2(3H)-yl)prop-1-
enyl]phenyl}acetamide (1h)
Synthesis of N-{3-[4-(2-(4-(4-nitrophenyl)piperidin-1-yl)-
2-oxoethyl)phenyl] propyl}-1H-pyrrolo[3,4-b]quinolin-
3(2H)-one (2c)
The general synthetic method described above afforded 1h
as yellowish solid. Yield 79 %, mp 172–174 °C. IR (KBr, v
cm-1): 2944, 2833, 1532, 1405, 1238, 1127, 1056, 963,
765; 1H NMR (500 MHz, DMSO-d6): d 3.38–3.48 (m, 4H,
2 9 CH2), 4.47 (d, J = 5.84 Hz, 2H, CH2), 4.66 (t,
J = 5.24 Hz, 2H, CH2), 4.70 (s, 2H, CH2), 6.36–6.44 (m,
1H, =CH), 6.68 (d, J = 15.74 Hz, 1H, =CH), 7.25 (d,
J = 7.34 Hz, 2H, Ar–H), 7.43 (d, J = 7.34 Hz, 2H,
The general synthetic method described above afforded 2c
as yellow solid. Yield 69 %, mp 182–184 °C. IR (KBr, v
cm-1): 2944, 2841, 1687, 1635, 1460, 1371, 1210, 1131,
1
1017, 987, 768; H NMR (500 MHz, DMSO-d6): d 1.97
(m, 2H, CH2), 2.62 (t, J = 7.34 Hz, 2H, CH2), 3.39–3.50
(m, 4H, 2 9 CH2), 3.57–3.73 (m, 6H, 3 9 CH2), 4.65 (s,
2H, CH2), 6.90 (d, J = 9.75 Hz, 2H, Ar–H), 7.14 (d,
J = 7.80 Hz, 2H, Ar–H), 7.20 (d, J = 7.80 Hz, 2H,
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