R. Venkatesh et al. / European Journal of Medicinal Chemistry 94 (2015) 87e101
97
CDCl3):
d
13.7, 22.2, 23.7, 25.2, 29.3, 29.6, 31.3, 49.8, 56.2, 56.3,105.8,
(s, 3H, CH3), 3.98 (s, 3H, OCH3), 4.00 (s, 3H, OCH3), 5.31 (d,
J ¼ 15.8 Hz, 1Ha, CH2), 5.57 (d, J ¼ 15.8 Hz, 1Hb, CH2), 7.11 (s, 1H,
AreH), 7.32e7.39 (d, J ¼ 6.8 Hz, 1H, AreH), 7.40e7.49 (m, 3H,
AreH), 7.51e7.57 (m, 2H, AreH), 7.58e7.66 (m, 6H, AreH), 7.73 (s,
1H, AreH), 7.81 (d, J ¼ 8.3 Hz, 2H, AreH); 13C NMR (75 MHz, CDCl3):
107.5,113.4,128.7,129.0,130.0,130.2,133.1,136.3,143.9,149.1,152.5,
155.5, 161.2; ESI MS: m/z ¼ 462 [MþH]þ; HRMS calculated for
C
26H32N503: 462.2427, Found: 462.2409.
6.5.8. 3-(2-((4-(1-Hydroxyhexyl)-1H-1,2,3-triazol-1-yl)methyl)
d 29.6, 50.0, 56.2, 56.3, 105.8, 107.6, 113.4, 120.4, 126.1, 126.8, 127.3,
phenyl)-6,7-dimethoxy-2-methyl quinazolin-4(3H)-one (4h)
127.4, 128.7, 128.9, 129.2, 130.1, 130.2, 130.3, 132.9, 136.3, 140.4,
140.8, 143.9, 147.7, 149.2, 152.4, 155.5, 161.2; ESI MS: m/z ¼ 530
[MþH]þ; HRMS calculated for C32H28N503: 530.2114, Found:
530.2169.
Yield 85%; mp 155e158 ꢀC; IR (KBr)
y
in cmꢁ1: 2928, 1684, 1471,
1378,1276,1126, 776; 1H NMR (300 MHz, CDCl3):
d 0.87 (s, 3H, CH3),
1.27 (s, 6H, 3CH2), 1.71e1.91 (bs, 2H, CH2), 1.98 (d, J ¼ 8.1 Hz, 3H,
CH3), 4.01 (s, 3H, OCH3), 4.03 (s, 3H, OCH3), 4.73e4.97 (bs, 1H, CH),
5.24 (d, J ¼ 15.2 Hz, 1Ha, CH2), 5.48 (d, J ¼ 15.2 Hz, 1Hb, CH2), 7.11 (s,
1H, AreH), 7.19e7.25 (m, 1H, AreH), 7.34e7.45 (bs, 2H, AreH),
7.50e7.56 (bs, 2H, AreH), 7.59 (s, 1H, AreH); 13C NMR (75 MHz,
6.5.13. 6,7-Dimethoxy-2-methyl-3-(2-((4-(phenanthren-9-yl)-1H-
1,2,3-triazol-1-yl)methyl)phenyl) quinazolin-4(3H)-one (4m)
Yield 85%; mp 94e97 ꢀC; IR (KBr)
y
in cmꢁ1: 3010, 2935, 2849,
CDCl3):
d
13.9, 22.5, 23.6, 23.7, 25.0, 25.1, 29.6, 31.5, 31.5, 56.2, 56.3,
1668, 1508, 1395, 1256, 1028, 751; 1H NMR (300 MHz, CDCl3):
d 2.12
105.8, 107.4, 113.4, 113.4, 128.8, 130.2, 130.3, 132.8, 136.4, 143.8,
143.8, 149.1, 152.5, 152.6, 155.5, 161.1; ESI MS: m/z ¼ 478 [MþH]þ;
HRMS calculated for C26H32N504: 478.2376, Found: 478.2429.
(s, 3H, CH3), 3.93 (s, 3H, OCH3), 3.96 (s, 3H, OCH3), 5.40 (d,
J ¼ 15.2 Hz, 1Ha, CH2), 5.67 (d, J ¼ 15.2 Hz, 1Hb, CH2), 7.10 (s, 1H,
AreH), 7.53e7.73 (m, 9H, AreH), 7.79 (s, 1H, AreH), 7.90 (s, 2H,
AreH), 8.34 (d, J ¼ 8.3 Hz, 1H, AreH), 8.64e8.78 (m, 2H, AreH); 13
C
6.5.9. 6,7-Dimethoxy-3-(2-((4-(3-methoxyphenyl)-1H-1,2,3-
NMR (75 MHz, CDCl3): d 29.6, 50.1, 56.2, 56.2, 105.7, 107.4, 113.3,
triazol-1-yl)methyl)phenyl)-2-methyl quinazolin-4(3H)-one (4i)
122.4, 122.6, 122.8, 123.5, 126.1, 126.5, 126.7, 126.8, 127.0, 127.6,
128.3, 128.5, 128.7, 128.9, 130.3, 131.1, 131.9, 132.0, 132.7, 132.8,
136.4, 143.7, 147.0, 149.0, 152.4, 155.4, 161.2; ESI MS: m/z ¼ 554
[MþH]þ; HRMS calculated for C34H28N503: 554.2114, Found:
554.2171.
Yield 85%; mp 88e91 ꢀC; IR (KBr)
y
in cmꢁ1: 2927, 1666, 1506,
1394, 1219, 1025, 772; 1H NMR (300 MHz, CDCl3):
d 2.06 (s, 3H,
CH3), 3.84 (s, 3H, OCH3), 3.98 (s, 3H, OCH3), 4.01 (s, 3H, OCH3), 5.29
(d, J ¼ 15.1 Hz, 1Ha, CH2), 5.54 (d, J ¼ 15.1 Hz, 1Hb, CH2), 6.83e6.89
(m, 1H, AreH), 7.12 (s, 1H, AreH), 7.29 (s, 1H, AreH), 7.34e7.42 (m,
3H, AreH), 7.50e7.55 (m, 3H, AreH), 7.58 (s, 1H, AreH), 7.69 (s, 1H,
6.5.14. 3-(2-((4-(Hydroxymethyl)-1H-1,2,3-triazol-1-yl)methyl)
AreH); 13C NMR (75 MHz, CDCl3):
d
29.5, 49.9, 55.2, 56.1, 56.2,105.7,
phenyl)-6,7-dimethoxy-2-methyl quinazolin-4(3H)-one (4n)
107.4, 110.7, 113.3, 114.1, 118.0, 120.5, 128.8, 129.6, 130.0, 130.1, 130.2,
131.5, 132.8, 136.3, 143.8, 147.8, 149.0, 152.4, 155.4, 159.8, 161.1; ESI
MS: m/z ¼ 484 [MþH]þ; HRMS calculated for C27H26N504: 484.1907,
Found: 484.1961.
Yield 85%; mp 105e108 ꢀC; IR (KBr) in cmꢁ1: 2928, 1685, 1378,
y
1276, 1122, 776; 1H NMR (300 MHz, CDCl3):
d 2.00 (s, 3H, CH3), 4.01
(s, 3H, OCH3), 4.03 (s, 3H, OCH3), 4.71 (s, 2H, CH2), 5.23 (d,
J ¼ 15.2 Hz, 1Ha, CH2), 5.49 (d, J ¼ 15.2 Hz, 1Hb, CH2), 7.12 (s, 1H,
AreH), 7.20e7.25 (m, 1H, AreH), 7.35e7.42 (m, 1H, AreH), 7.48 (d,
J ¼ 7.1 Hz, 1H, AreH), 7.50e7.56 (m, 2H, AreH), 7.58 (s, 1H, AreH);
6.5.10. 6,7-Dimethoxy-2-methyl-3-(2-((4-(m-tolyl)-1H-1,2,3-
triazol-1-yl) methyl) phenyl) quinazolin-4(3H)-one (4j)
13C NMR (75 MHz, CDCl3):
d 29.6, 50.0, 55.5, 56.3, 56.4, 105.8, 107.4,
Yield 85%; mp 87e90 ꢀC; IR (KBr)
y
in cmꢁ1: 2922, 1669, 1509,
113.5, 123.9, 126.8, 128.9, 130.3, 132.8, 136.3, 139.5, 142.4, 143.8,
149.2, 152.6, 155.7, 161.1; ESI MS: m/z ¼ 408 [MþH]þ; HRMS
calculated for C21H22N504: 408.1594, Found: 408.1656.
1394, 1219, 1025, 778; 1H NMR (300 MHz, CDCl3):
d 2.06 (s, 3H,
CH3), 2.38 (s, 3H, CH3), 4.00 (s, 3H, OCH3), 4.02 (s, 3H, OCH3), 5.30
(d, J ¼ 15.4 Hz, 1Ha, CH2), 5.56 (d, J ¼ 15.4 Hz, 1Hb, CH2), 7.08e7.16
(m, 2H, AreH), 7.30 (s, 1H, AreH), 7.36e7.42 (m, 1H, AreH),
6.5.15. 3-(2-((4-(2-Hydroxyethyl)-1H-1,2,3-triazol-1-yl)methyl)
7.48e7.57 (m, 4H, AreH), 7.59 (s, 2H, AreH), 7.67 (s, 1H, AreH); 13
C
phenyl)-6,7-dimethoxy-2-methyl quinazolin-4(3H)-one (4o)
NMR (75 MHz, CDCl3):
d
19.1, 29.6, 56.2, 56.2, 71.7, 105.8, 107.5,
Yield 85%; mp 92e95 ꢀC; IR (KBr) in cmꢁ1: 2928, 1683, 1378,
y
113.4, 120.3, 122.8, 126.3, 128.5, 128.7, 128.9, 130.1, 130.2, 130.8,
132.3, 132.9, 136.3, 138.3, 143.9, 149.1, 152.4, 155.4, 161.2, 167.7; ESI
MS: m/z ¼ 468 [MþH]þ; HRMS calculated for C27H26N503: 468.1957,
Found: 468.2021.
1276, 1126, 776; 1H NMR (300 MHz, CDCl3):
d 1.95 (s, 3H, CH3),
2.74e3.01 (m, 2H, CH2), 3.81e3.95 (m, 2H, CH2), 4.00 (s, 3H, OCH3),
4.03 (s, 3H, OCH3), 5.36 (dd, J ¼ 12.4, 15.1 Hz, 2H, CH2), 7.12 (s, 1H,
AreH), 7.20e7.25 (m, 1H, AreH), 7.34e7.40 (m, 1H, AreH),
7.48e7.65 (m, 4H, AreH); 13C NMR (75 MHz, CDCl3):
d 23.6, 29.0,
6.5.11. 6,7-Dimethoxy-2-methyl-3-(2-((4-(p-tolyl)-1H-1,2,3-
29.6, 56.3, 56.4, 71.7, 105.6, 106.6, 107.4, 116.3, 119.8, 123.3, 125.4,
128.5, 129.1, 130.3, 130.7, 131.0, 136.8, 145.7, 152.5, 166.5; ESI MS: m/
z ¼ 422 [MþH]þ; HRMS calculated for C22H24N504: 422.1750,
Found: 422.1810.
triazol-1-yl)methyl)phenyl)quinazolin-4(3H)-one (4k)
Yield 85%; mp 170e173 ꢀC; IR (KBr) in cmꢁ1: 2922, 1668, 1509,
y
1394, 1218, 1025, 778; 1H NMR (300 MHz, CDCl3):
d 2.09 (s, 3H,
CH3), 2.38 (s, 3H, CH3), 4.01 (s, 3H, OCH3), 4.04 (s, 3H, OCH3), 5.30 (d,
J ¼ 15.4 Hz, 1Ha, CH2), 5.56 (d, J ¼ 15.4 Hz, 1Hb, CH2), 7.11 (s, 1H,
AreH), 7.22 (d, J ¼ 7.7 Hz, 1H, AreH), 7.37e7.43 (m, 1H, AreH),
7.53e7.58 (m, 4H, AreH), 7.61 (s, 1H, AreH), 7.65 (d, J ¼ 8.8 Hz, 1H,
6.5.16. 3-(2-((4-(4-Methoxyphenyl)-1H-1,2,3-triazol-1-yl)methyl)
phenyl)-2-methylquinazolin-4(3H)-one (4p)
Yield 85%; mp 178e181 ꢀC; IR (KBr)
y
in cmꢁ1: 2928, 1728, 1682,
AreH), 7.73e7.77 (m, 2H, AreH); 13C NMR (75 MHz, CDCl3):
d
19.0,
1470,1378, 1276, 1123, 772; 1H NMR (300 MHz, CDCl3):
d 2.11 (s, 3H,
29.6, 56.2, 56.2, 71.7, 105.7, 107.5, 113.7, 120.0, 124.1, 125.5, 128.7,
129.3, 130.0, 130.2, 130.8, 132.2, 132.9, 136.2, 137.9, 143.8, 148.0,
149.0, 152.4, 155.4, 161.1, 167.5; ESI MS: m/z ¼ 468 [MþH]þ; HRMS
calculated for C27H26N503: 468.1957, Found: 468.2019.
CH3), 3.84 (s, 3H, OCH3), 5.27 (d, J ¼ 15.2 Hz, 1Ha, CH2), 5.55 (d,
J ¼ 15.2 Hz, 1Hb, CH2), 6.93 (d, J ¼ 8.8 Hz, 2H, AreH), 7.09e7.16 (m,
1H, AreH), 7.33e7.43 (m, 1H, AreH), 7.43e7.50 (m, 1H, AreH), 7.53
(s, 1H, AreH), 7.55 (d, J ¼ 3.3 Hz, 1H, AreH), 7.61e7.76 (m, 4H,
AreH), 7.79 (t, J ¼ 6.6, 15.1 Hz, 1H, AreH), 8.31 (d, J ¼ 7.7 Hz, 1H,
6.5.12. 3-(2-((4-([1,10-Biphenyl]-4-yl)-1H-1,2,3-triazol-1-yl)
AreH); 13C NMR (75 MHz, CDCl3):
d 29.5, 49.7, 55.3, 106.1, 110.6,
methyl)phenyl)-6,7-dimethoxy-2-methyl quinazolin-4(3H)-one (4l)
114.1, 119.5, 124.4, 127.0, 127.9, 128.7, 130.0, 130.4, 131.5, 132.9, 134.7,
135.0, 147.5, 148.1, 158.7, 162.9; ESI MS: m/z ¼ 424 [MþH]þ; HRMS
calculated for C25H2202N5: 424.1768, Found: 424.1766.
Yield 85%; mp 80e83 ꢀC; IR (KBr)
y
in cmꢁ1: 3010, 2939, 2841,
1668,1500,1395,1259,1028, 759; 1H NMR (300 MHz, CDCl3):
d 2.08