R. Kumar et al. / European Journal of Medicinal Chemistry 80 (2014) 83e91
89
collected and then extracted with chloroform. The combined
organic extracts were washed with brine and water and finally
dried with anhydrous sodium sulfate. Pure compounds were iso-
lated after column chromatography and recrystallized from suit-
able solvent.
7.22 (t, J ¼ 7.5 Hz, 1H, Ar-H), 4.28 (s, 2H, CH2); 13C NMR
(400 MHz, DMSO-d6) d 176.76, 171.64, 140.85, 140.15, 135.47, 133.39,
132.89, 131.72, 129.45, 125.98, 125.57, 125.15, 124.81, 123.96, 123.41,
121.70, 120.95, 120.45, 117.29, 111.20, 61.70; LCeMS (m/z): negative
mode 372.00 [M ꢁ 1]þ; Anal. Calcd for C21H15N3O4 (373.36): C,
67.56; H, 4.05; N, 11.25. Found: C, 67.56; H, 4.095; N, 10.56.
4.1.2.1. 2-(9-oxoacridin-10(9H)-yl)-N-phenylacetamide
(13a). Yield: 70%; Pale yellow crystals; m.p: 204e205 ꢀC; IR (KBr,
cmꢁ1) 3271.73, 3085.40, 2951.35,1674.68,1613.46,1598.24,1491.60,
4.1.2.6. 2-(9-oxoacridin-10(9H)-yl)-N-(p-tolyl)acetamide
Yield: 69%; Yellowish gray crystals; m.p: 228e230 ꢀC; (KBr, cmꢁ1
3231.43, 2919.63, 2850.55, 1652.42, 1629.17, 1590.93, 1463.52,
1383.83, 1246.92; 1H NMR (400 MHz, DMSO-d6)
10.12 (br s, 1H,
NH), 7.73 (ddd, J ¼ 17.2, 11.3, 5.2 Hz, 1H, Ar-H), 7.54e7.46 (m, 3H, Ar-
H), 7.25 (dt, J ¼ 12.5, 6.2 Hz, 6H, Ar-H), 7.11 (d, J ¼ 8.3 Hz, 2H, Ar-H),
4.45 (s, 2H, CH2), 2.28 (s, 3H, CH3); 13C NMR (400 MHz, DMSO-d6)
(13f).
)
1461.22, 1283.13; 1H NMR (400 MHz, DMSO-d6)
d 10.52 (br s, 1H,
NH), 8.42 (d, J ¼ 6.9 Hz,1H, Ar-H), 8.28 (d, J ¼ 8.3 Hz,1H, Ar-H), 7.77 (t,
J ¼ 7.4 Hz,1H, Ar-H), 7.66 (t, J ¼ 10.2 Hz, 2H, Ar-H), 7.53 (d, J ¼ 8.4 Hz,
1H, Ar-H), 7.46e7.40 (m, 4H, Ar-H), 7.31 (q, J ¼ 7.7 Hz, 2H, Ar-H), 7.22
(t, J ¼ 7.4 Hz,1H, Ar-H), 4.52 (s, 2H, CH2); 13C NMR (400 MHz, DMSO-
d
d6)
d
176.77, 170.85, 140.86, 138.46, 133.40, 129.44, 128.85, 128.81,
d 176.77,170.59,140.87,136.00,135.94,134.10,133.39,132.27,128.96,
128.77, 128.58, 125.99, 125.19, 123.36, 121.56, 120.95, 120.46, 119.56,
119.33, 119.18, 117.30, 61.86; LCeMS (m/z): negative mode 327.00
[M ꢁ 1]þ; Anal. Calcd for C21H16N2O2 (328.36): C, 76.81; H, 4.91; N,
8.53. Found: C, 75.09; H, 5.106; N, 8.46.
126.55, 125.99, 125.04, 121.57, 121.01, 120.95, 120.47, 119.54, 119.21,
117.30, 115.84, 61.85, 20.39; LCeMS (m/z): negative mode 341.00
[M ꢁ 1]þ; Anal. Calcd for C22H18N2O2 (342.39): C, 77.17; H, 5.30; N,
8.18. Found: C, 77.09; H, 5.336; N, 8.18.
4.1.2.2. N-(3-chlorophenyl)-2-(9-oxoacridin-10(9H)-yl)acetamꢁid1e
4.1.2.7. N-(4-methoxyphenyl)-2-(9-oxoacridin-10(9H)-yl)acetamide
(13b). Yield: 66%; Yellow crystals; m.p: 220e222 ꢀC; IR (KBr, cm
)
(13g). Yield: 73%; Pale yellow crystals; m.p: 224e226 ꢀC; IR (KBr,
3271.72, 2948.11, 2849.30, 1681.13, 1613.91, 1595.31, 1478.91,
cmꢁ1
)
3292.23, 2922.60, 2851.95, 1677.33, 1629.83, 1593.99,
1429.85, 1253.87, 779.22; 1H NMR (400 MHz, DMSO-d6)
d
11.64 (br
1481.16, 1450.47, 1372.12, 1265.11; 1H NMR (400 MHz, DMSO-d6)
s, 1H, NH), 8.41e8.25 (m, 2H, Ar-H), 7.70e7.66 (m, 3H, Ar-H), 7.46
(ddd, J ¼ 18.9, 10.4, 5.9 Hz, 4H, Ar-H), 7.44e7.21 (m, 3H, Ar-H), 4.49
d
10.06 (br s, 1H, NH), 8.42e8.12 (m, 2H, Ar-H), 7.78 (d, J ¼ 13.5 Hz,
1H, Ar-H), 7.54e7.50 (m, 3H, Ar-H), 7.32e7.22 (m, 2H, Ar-H), 6.90
(dd, J ¼ 15.1, 8.2 Hz, 4H, Ar-H), 4.15 (s, 2H, CH2), 3.75 (s, 3H, OCH3);
(s, 2H, CH2); 13C NMR (400 MHz, DMSO-d6)
d 176.79, 171.36, 140.86,
139.97, 139.87, 133.35, 133.15, 132.94, 130.47, 130.36, 130.20, 129.42,
126.51, 125.99, 123.05, 120.92, 120.48, 119.06, 117.98, 117.29, 61.89;
LCeMS (m/z): negative mode 360.90 [M ꢁ 1]þ; Anal. Calcd for
13C NMR (400 MHz, DMSO-d6)
d 176.79, 170.35, 140.87, 140.27,
133.37, 131.75, 131.60, 129.43, 126.73, 125.99, 123.27, 121.53, 121.14,
120.94, 120.48, 117.30, 114.06, 113.88, 113.67, 111.71, 61.82, 55.06;
LCeMS (m/z): positive mode 359.10 [M]þ, 381.20 [M þ Na]þ; Anal.
Calcd for C22H18N2O3 (358.39): C, 73.73; H, 5.06; N, 7.82. Found: C,
73.12; H, 4.911; N, 7.83.
C
21H15ClN2O2 (362.81): C, 69.52; H, 4.17; N, 7.72. Found: C, 69.96; H,
4.095; N, 7.63.
4.1.2.3. N-(4-chlorophenyl)2-(9-oxoacridine-10(9H)-yl)acetamꢁid1e
(13c). Yield: 60%; Yellow crystals; m.p: 216e218 ꢀC; IR (KBr, cm
)
4.1.2.8. N-(4-hydroxyphenyl)-2-(9-oxoacridin-10(9H)-yl)acetamꢁid1e
3274.23, 3093.49, 2922.28, 1669.53, 1616.30, 1582.21, 1474.28,
(13h). Yield: 64%; Yellow crystals; m.p: 230e232 ꢀC; IR (KBr, cm
)
1251.44, 797.87; 1H NMR (400 MHz, DMSO-d6)
d
10.30 (br s, 1H,
3400.53, 3305.98, 2922.84, 2853.30, 1662.65, 1632.02, 1598.18,
NH), 8.42e8.08 (m, 1H, Ar-H), 7.64 (dd, J ¼ 15.6, 8.0 Hz, 3H, Ar-H),
7.43e7.30 (m, 5H, Ar-H), 7.28 (d, J ¼ 8.8 Hz, 3H, Ar-H), 4.52 (s, 2H,
1471.22, 1466.08, 1257.79; 1H NMR (400 MHz, DMSO-d6)
d
11.63 (br
s, 1H, OH), 10.57 (br s, 1H, NH), 8.26 (d, J ¼ 7.1 Hz, 2H, Ar-H), 7.70e
7.66 (m, 4H, Ar-H), 7.55 (dd, J ¼ 17.4, 8.0 Hz, 2H, Ar-H), 7.31e7.28 (m,
4H, Ar-H), 4.52 (s, 2H, CH2); 13C NMR (400 MHz, DMSO-d6)
CH2); 13C NMR (400 MHz, DMSO-d6)
d 176.78, 171.10, 140.87, 140.23,
138.81, 137.47, 137.39, 133.36, 130.82, 129.43, 128.74, 128.44, 126.87,
125.99, 121.58, 121.15, 120.93, 120.88, 120.48, 117.29, 61.89; LCeMS
(m/z): positive mode 360.90 [M ꢁ 1]þ; Anal. Calcd for C21H15ClN2O2
(362.81): C, 69.52; H, 4.17; N, 7.72. Found: C, 69.96; H, 4.120; N, 7.63.
d
176.76,170.08,140.85,133.42,132.00,131.31,130.07,129.87,129.45,
125.98, 121.64, 121.35, 121.09, 120.97, 120.45, 117.29, 115.02, 114.93,
114.74, 114.64, 61.76; LCeMS (m/z): positive mode 346.00 [M þ 1]þ;
Anal. Calcd for C21H16N2O3 (344.36): C, 73.24; H, 4.68; N, 8.13.
Found: C, 73.12; H, 4.707; N, 8.18.
4.1.2.4. N-(2-nitrophenyl)-2-(9-oxoacridin-10(9H)-yl)acetamide
(13d). Yield: 65%; Yellowish orange crystals; m.p: 235e237 ꢀC; IR
(KBr, cmꢁ1) 3274.52, 2919.74, 2851.09, 1671.59, 1606.40, 1571.52,
1493.88, 1451.53, 1329.73, 1277.49; 1H NMR (400 MHz, DMSO-d6)
4.1.2.9. 2-(9-oxoacridin-10(9H)-yl)-N-(4-(trifluoromethyl) phenyl)
acetamide) (13i). Yield: 62%; Yellow crystals; m.p: 248e250 ꢀC; IR
(KBr, cmꢁ1) 3267.85, 2920.74, 2850.40, 1671.29, 1626.12, 1599.37,
d
10.81 (br s, 1H, NH), 8.27 (d, J ¼ 7.3 Hz,1H, Ar-H), 8.08 (dd, J ¼ 10.5,
5.7 Hz, 3H, Ar-H), 7.85 (t, J ¼ 7.0 Hz, 1H, Ar-H), 7.74e7.63 (m, 4H, Ar-
H), 7.56 (d, J ¼ 8.3 Hz, 1H, Ar-H), 7.37 (t, J ¼ 7.9 Hz, 1H, Ar-H), 7.22 (t,
J ¼ 7.1 Hz, 1H, Ar-H), 4.35 (s, 2H, CH2); 13C NMR (400 MHz, DMSO-
1434.34,1243.54,1120.64; 1H NMR (400 MHz, DMSO-d6)
d 10.54 (br
s,1H, NH), 8.43e8.09 (m,1H, Ar-H), 7.84e7.80 (m, 2H, Ar-H), 7.75 (d,
J ¼ 8.6 Hz, 3H, Ar-H), 7.66 (d, J ¼ 8.4 Hz, 3H, Ar-H), 7.56 (dd, J ¼ 26.5,
8.5 Hz, 3H, Ar-H), 4.22 (s, 2H, CH2); 13C NMR (400 MHz, DMSO-d6)
d6)
d 176.76, 171.63, 140.85, 140.15, 135.47, 134.88, 133.38, 132.90,
131.72, 129.45, 125.98, 123.95, 123.40, 122.15, 121.70, 120.94, 120.46,
117.60, 117.29, 111.20, 61.70; LCeMS (m/z): negative mode 371.90
[M ꢁ 1]þ; Anal. Calcd for C21H15N3O4 (373.36): C, 67.56; H, 4.05; N,
11.25. Found: C, 67.76; H, 3.803; N, 10.72.
d 176.82, 171.59, 164.31, 140.88, 140.62, 139.29, 139.21, 133.29,
129.98, 129.71, 129.64, 129.39, 128.88, 125.97, 123.11, 122.11, 122.07,
121.61, 120.86, 120.49, 117.27, 61.89; LCeMS (m/z): positive mode
397.10 [M þ 1]þ; Anal. Calcd for C22H15F3N2O2 (396.36): C, 66.67; H,
3.81; N, 7.07. Found: C, 66.66; H, 3.803; N, 7.01.
4.1.2.5. N-(4-nitrophenyl)-2-(9-oxoacridin-10(9H)-yl)acetamide
(13e). Yield: 72%; Yellowish orange crystals; m.p: 244e245 ꢀC; IR
(KBr, cmꢁ1) 3314.66, 3092.05, 2922.98, 1673.18, 1615.12, 1600.00,
1552.75, 1467.19, 1338.21, 1257.58; 1H NMR (400 MHz, DMSO-d6)
4.1.2.10. 2-(9-oxoacridin-10(9H)-yl)-N-(3-(trifluoromethyl)phenyl)
acetamide (13j). Yield: 65%; Yellow crystals; m.p: 210e212 ꢀC; IR
(KBr, cmꢁ1) 3300.90, 2920.83, 2851.05, 1671.01, 1629.15, 1597.36,
1492.07, 1465.28, 1245.18, 1124.16; 1H NMR (400 MHz, DMSO-d6)
d
10.83 (br s, 1H, NH), 8.31e8.16 (m, 6H, Ar-H), 7.86 (d, J ¼ 9.2 Hz,
2H, Ar-H), 7.76e7.66 (m, 2H, Ar-H), 7.54 (d, J ¼ 8.4 Hz, 1H, Ar-H),
d
10.58 (br s, 1H, NH), 8.06 (s, 1H, Ar-H), 7.84e7.69 (m, 3H, Ar-H),