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Organic & Biomolecular Chemistry
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7.26 (m, 4H), 7.25 – 7.16 (m, 7H), 7.02 (d, J = 4.3 Hz, 2H) ppm; m/z (ESI): calcd. for C27H17Cl2N2O [M+H]+ 455.0718, found
13C NMR (100 MHz, CDCl3) δC 156.13, 139.58, 137.94, 134.67, 455.0708.
DOI: 10.1039/C5OB02045J
134.41, 132.19, 131.23, 130.14, 128.88, 128.86, 128.52, 5,6-bis(4-bromophenyl)-8H-indazolo[1,2-a]cinnolin-8-one (7f)
128.19, 128.13, 127.41, 127.36, 126.96, 125.22, 124.56, Yield: 85 %, Greenish yellow Solid; mp: 254-256 oC; FT-IR (cm-1)
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123.97, 122.98, 118.84, 113.94, 111.05 ppm; HRMS m/z (ESI): Neat; 2922, 2712, 2079, 1649, 1633, 1486, 1463, 1012, 749; H
calcd. for C27H19N2O [M+H]+ 387.1497, found 387.1490.
5,6-di-p-tolyl-8H-indazolo[1,2-a]cinnolin-8-one (7b)
Yield: 94 %, Greenish yellow Solid; mp: 224-226 oC; FT-IR (cm-1) Hz, 1H), 7.45 (d, J = 8.4 Hz, 2H), 7.40 – 7.28 (m, 4H), 7.07 (dt, J
NMR (400 MHz, CDCl3) δH 7.99 – 7.93 (m, 1H), 7.87 (d, J = 8.4
Hz, 1H), 7.77 (ddd, J = 8.4, 7.1, 1.3 Hz, 1H), 7.70 (dd, J = 8.3, 1.0
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Neat; 2926, 2881, 1691, 1610, 1463, 1351, 1294, 818, 741; H = 8.9, 2.7 Hz, 4H), 7.02 (dd, J = 7.5, 1.1 Hz, 1H), 6.95 (dd, J =
NMR (400 MHz, CDCl3) δH 7.96 (dt, J = 7.8, 1.0 Hz, 1H), 7.86 (d, 7.8, 1.5 Hz, 1H) ppm; 13C NMR (101 MHz, CDCl3) δC 156.20,
J = 8.4 Hz, 1H), 7.75 (ddd, J = 8.4, 7.2, 1.3 Hz, 1H), 7.69 (d, J = 139.67, 137.95, 133.75, 133.07, 132.75, 132.49, 131.71,
8.2 Hz, 1H), 7.38 – 7.32 (m, 1H), 7.29 – 7.26 (m, 1H), 7.09 (d, J = 131.62, 130.88, 130.12, 129.36, 126.80, 124.61, 124.57,
6.3 Hz, 6H), 7.04 – 6.95 (m, 4H), 2.32 (s, 3H), 2.26 (s, 3H) ppm; 124.13, 123.24, 122.76, 122.66, 121.96, 118.59, 113.96, 111.20
13C NMR (100 MHz, CDCl3) δC 156.15, 139.68, 138.04, 137.77, ppm; HRMS m/z (ESI): calcd. for C27H17Br2N2O [M+H]+
136.94, 134.68, 132.05, 131.48, 131.04, 129.98, 128.93, 542.9708, found 542.9702.
128.65, 128.55, 128.18, 126.99, 125.58, 124.52, 123.90, 5-methyl-6-phenyl-8H-indazolo[1,2-a]cinnolin-8-one (7g)
123.20, 122.96, 119.07, 114.04, 110.93, 21.42, 21.28 ppm; Yield: 87 %, Greenish yellow Solid; mp: 180-182 oC; FT-IR (cm-1)
HRMS m/z (ESI): calcd. for C29H22N2NaO [M+Na]+ 437.1630, Neat; 2926, 2856, 2063, 1681, 1633, 1488, 1452, 1284, 1144,
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found 437.1587.
749; H NMR (400 MHz, CDCl3) δH 7.93 (d, J = 7.8 Hz, 1H), 7.82
(d, J = 8.3 Hz, 1H), 7.75 – 7.69 (m, 1H), 7.66 (dd, J = 8.2, 1.1 Hz,
1H), 7.46 – 7.40 (m, 4H), 7.38 – 7.35 (m, 2H), 7.31 (dd, J = 7.7,
5,6-bis(4-methoxyphenyl)-8H-indazolo[1,2-a]cinnolin-8-one
(7c)
Yield: 85 %, Greenish yellow Solid; mp: 216-218 oC; FT-IR (cm-1) 6.6 Hz, 2H), 7.18 (td, J = 7.6, 1.1 Hz, 1H), 2.09 (s, 3H) ppm; 13C
Neat; 2925, 2856, 1682, 1643, 1463, 1293, 1177, 1033, 830, NMR (100 MHz, CDCl3) δC 155.77, 139.78, 138.47, 133.58,
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746; H NMR (400 MHz, CDCl3) δH 7.96 (d, J = 7.9 Hz, 1H), 7.86 131.90, 131.87, 129.84, 128.71, 128.55, 127.97, 125.69,
(d, J = 8.2 Hz, 1H), 7.75 (t, J = 7.6 Hz, 1H), 7.69 (d, J = 8.2 Hz, 124.91, 124.43, 124.13, 123.02, 119.25, 116.23, 114.14,
1H), 7.35 (t, J = 7.4 Hz, 1H), 7.28 (s, 1H), 7.13 (d, J = 8.3 Hz, 4H), 110.87, 13.75 ppm; HRMS m/z (ESI): calcd. for C22H16N2O
7.02 (d, J = 6.8 Hz, 2H), 6.83 (d, J = 7.3 Hz, 2H), 6.73 (d, J = 7.4 [M+H]+ 325.1341, found 325.1335.
Hz, 2H), 3.79 (s, 3H), 3.75 (s, 3H) ppm; 13C NMR (100 MHz, 5,6-dipropyl-8H-indazolo[1,2-a]cinnolin-8-one (7h)
CDCl3) δC 159.12, 158.68, 156.17, 139.68, 138.03, 134.72, Yield: 80 %, Greenish yellow Solid; mp: 192-194 oC; FT-IR (cm-1)
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132.32, 132.03, 131.47, 128.59, 126.88, 126.77, 125.73, Neat; 2922, 2132, 2079, 1638, 1630, 1482, 1456, 1010, 748; H
124.50, 123.91, 123.88, 122.95, 122.78, 119.08, 114.03, NMR (400 MHz, CDCl3) δH 8.04 – 7.98 (m, 1H), 7.76 (d, J = 8.4
113.71, 112.91, 110.95, 55.16, 55.04 ppm; HRMS m/z (ESI): Hz, 1H), 7.68 (ddd, J = 8.4, 7.1, 1.3 Hz, 1H), 7.60 (dd, J = 8.0, 1.2
calcd. for C29H23N2O3 [M+H]+ 447.1709, found 447.2716.
Hz, 1H), 7.36 – 7.29 (m, 2H), 7.21 (td, J = 7.8, 1.5 Hz, 1H), 7.12
5,6-bis(4-fluorophenyl)-8H-indazolo[1,2-a]cinnolin-8-one (7d) (td, J = 7.6, 1.2 Hz, 1H), 3.20 – 3.11 (m, 2H), 2.62 – 2.52 (m,
Yield: 75 %, Greenish yellow Solid; mp: 218-220 oC; FT-IR (cm-1) 2H), 1.64 (dq, J = 15.9, 7.6 Hz, 4H), 1.04 (dt, J = 11.8, 7.3 Hz,
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Neat; 2930, 2858, 1638, 1506, 1353, 1297, 1223, 834, 745; H 6H) ppm; 13C NMR (100 MHz, CDCl3) δC 156.81, 139.06, 137.95,
NMR (400 MHz, CDCl3) δH 7.96 (d, J = 7.8 Hz, 1H), 7.88 (d, J = 136.67, 131.76, 127.75, 124.48, 124.16, 124.06, 123.95,
8.4 Hz, 1H), 7.77 (ddd, J = 8.5, 7.1, 1.3 Hz, 1H), 7.71 (dd, J = 8.2, 122.70, 118.98, 118.21, 113.84, 111.21, 28.36, 28.05, 22.79,
1.0 Hz, 1H), 7.39 – 7.34 (m, 1H), 7.34 – 7.28 (m, 1H), 7.20 – 22.71, 14.32, 13.80 ppm; HRMS m/z (ESI): calcd. for C21H23N2O
7.14 (m, 4H), 7.07 – 6.95 (m, 4H), 6.93 – 6.87 (m, 2H) ppm; 13
C
[M+H]+ 319.1810, found 319.1801.
NMR (100 MHz, CDCl3) δC 179.99, 156.17, 139.58, 132.87, 5,6-di(thiophen-2-yl)-8H-indazolo[1,2-a]cinnolin-8-one (7i)
132.78, 132.38, 132.01, 131.93, 129.14, 126.76, 125.01, Yield: 94 %, Greenish yellow Solid; mp: 238-240 oC; FT-IR (cm-1)
124.55, 124.07, 123.10, 122.62, 122.62, 118.66, 115.57, Neat; 2922, 2856, 1691, 1691, 1628, 1483, 1462, 1359, 1275,
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115.35, 114.79, 114.58, 113.88, 111.17 ppm; HRMS m/z (ESI): 1231, 1117, 748; H NMR (400 MHz, CDCl3) δH 7.99 (d, J = 8.0
calcd. for C27H17F2N2O [M+H]+ 423.1309, found 423.1271.
Hz, 1H), 7.83 (d, J = 8.3 Hz, 1H), 7.81 – 7.74 (m, 1H), 7.65 (d, J =
5,6-bis(4-chlorophenyl)-8H-indazolo[1,2-a]cinnolin-8-one (7e) 8.2 Hz, 1H), 7.42 – 7.32 (m, 3H), 7.30 (dd, J = 7.4, 1.5 Hz, 1H),
Yield: 78 %, Greenish yellow Solid; mp: 202-204 oC; FT-IR (cm-1) 7.20 (dd, J = 7.8, 1.6 Hz, 1H), 7.13 – 7.03 (m, 4H), 6.94 (dd, J =
Neat; 2925, 2856, 1688, 1614, 1487, 1352, 1294, 1251, 1089, 5.0, 3.5 Hz, 1H) ppm; 13C NMR (100 MHz, CDCl3) δC 156.62,
1016, 821, 750; 1H NMR (400 MHz, CDCl3) δH 7.89 (d, J = 7.8 Hz, 140.60, 138.70, 134.74, 132.37, 131.66, 130.97, 130.61,
1H), 7.79 (d, J = 8.4 Hz, 1H), 7.70 (ddd, J = 8.4, 7.1, 1.3 Hz, 1H), 129.37, 127.97, 127.41, 127.16, 126.83, 126.17, 125.36,
7.63 (d, J = 7.9 Hz, 1H), 7.29 (ddd, J = 7.9, 7.1, 0.8 Hz, 1H), 7.26 124.62, 124.62, 12 4.26, 123.58, 119.37, 118.60, 114.64,
– 7.20 (m, 3H), 7.14 – 7.09 (m, 2H), 7.06 (dq, J = 8.5, 2.2 Hz, 110.90 ppm; HRMS m/z (ESI): calcd. for C23H15N2OS2 [M+H]+
4H), 6.96 (td, J = 7.6, 1.1 Hz, 1H), 6.88 (dd, J = 7.8, 1.6 Hz, 1H) 399.0626, found 399.0621.
ppm; 13C NMR (100 MHz, CDCl3) δC 156.20, 139.65, 137.94,
134.36, 133.82, 133.74, 132.61, 132.47, 132.46, 131.39, Cell viability assay
129.68, 129.32, 128.74, 127.93, 126.78, 124.70, 124.56,
124.11, 123.21, 122.66, 118.60, 113.94, 111.20 ppm; HRMS
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