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J. Grover et al. / European Journal of Medicinal Chemistry 80 (2014) 47e56
4.2.15. 1-(8-(2-Bromobenzyloxy)-1-hydroxy-3-methylnaphthalen-
2-yl)ethanone (1h)
4.2.21. 1,8-Dipropyloxy-3-methylanthracene-9,10-dione (2c)
Yellow solid. Yield 82%. mp: 112e114 ꢃC. 1H NMR (400 MHz,
White solid. Yield 60%. mp: 153e155 ꢃC. 1H NMR (400 MHz,
CDCl3)
d
(ppm): 1.12 (t, 6H, J ¼ 7.4 Hz, CH3), 1.91e1.97 (m, 4H, CH2)
CDCl3)
d
(ppm): 2.38 (s, 3H, AreCH3), 2.61 (s, 3H, COCH3), 5.40 (s,
2.45 (s, 3H, AreCH3), 4.07e4.11 (m, 4H, OCH2), 7.08 (s, 1H, H-2), 7.26
(d, 1H, J ¼ 7.7 Hz, H-7), 7.57 (t, 1H, J ¼ 8.16 Hz, H-6), 7.63 (s, 1H, H-4),
2H, OCH2), 6.83 (dd, 1H, J ¼ 5.88, 2.76 Hz, H-7), 7.12 (s, 1H, H-4),
7.27e7.38 (m, 4H, AreH), 7.53 (dd, 1H, J ¼ 7.60, 1.36 Hz, AreH), 7.67
(dd, 1H, J ¼ 7.96, 0.92 Hz, AreH), 9.70 (s, 1H, OH). 13C NMR
7.80 (dd, 1H, J ¼ 7.68, 0.92 Hz, H-5). 13C NMR (100 MHz, CDCl3)
d:
10.4, 22.0, 22.5, 71.3, 118.8, 119.7, 119.8, 120.3, 122.3, 124.7, 133.3,
134.6, 134.9, 144.5, 158.9, 159.1, 182.0, 184.5. IR (KBr, cmꢀ1) 2924,
2875, 1671, 1600, 1440, 1233. HRMS (ESI) m/z: Calcd for C21H22O4Na
[M þ Na]þ 361.1416; found 361.1415.
(100 MHz, CDCl3) d: 20.0, 32.3, 71.1, 105.4, 113.3, 119.8, 121.5, 123.3,
127.0, 128.0, 130.0, 130.4, 133.2, 134.1, 134.3, 136.7, 152.3, 155.4,
205.5. IR (KBr, cmꢀ1) 3364, 2917, 1691. HRMS (ESI) m/z: Calcd for
C
20H17BrO3Na [M þ Na]þ 407.0259; found 407.0259.
4.2.22. 1,8-Dibutoxy-3-methylanthracene-9,10-dione (2d)
Yellow solid. Yield 84%. mp: 97e99 ꢃC. 1H NMR (400 MHz,
4.2.16. 1-(1-(2-Bromobenzyloxy)-8-hydroxy-3-methylnaphthalen-
2-yl)ethanone (1h0)
CDCl3)
d
(ppm): 1.02 (t, 6H, J ¼ 7.12 Hz, CH3),1.58e1.64 (m, 4H, CH2),
White solid. Yield 33%. mp: 123e125 ꢃC. 1H NMR (400 MHz,
1.86e1.93 (m, 4H, CH2), 2.45 (s, 3H, AreCH3), 4.11e4.15 (m, 4H,
OCH2), 7.08 (s, 1H, H-2), 7.26e7.28 (m, 1H, H-7), 7.57 (t, 1H,
CDCl3)
2H, OCH2), 6.88 (d, 1H, J ¼ 7.6 Hz, H-7), 7.27e7.65 (m, 7H, AreH),
8.94 (s, 1H, OH). 13C NMR (100 MHz, CDCl3)
: 19.4, 33.0, 67.0, 110.6,
d (ppm): 2.38 (s, 3H, AreCH3), 2.63 (s, 3H, COCH3), 5.13 (s,
J ¼ 8.08 Hz, H-6), 7.62 (s, 1H, H-4), 7.80 (d, 1H, J ¼ 7.12 Hz, H-5). 13
C
NMR (100 MHz, CDCl3) d: 13.8, 19.2, 22.0, 31.2, 69.5, 118.7, 119.4,
d
119.6, 120.2, 122.3, 124.7, 133.3, 134.5, 134.8, 144.5, 158.9, 159.0,
182.0,184.5. IR (KBr, cmꢀ1) 2925, 2855,1666,1601,1323,1286,1232,
HRMS (ESI) m/z: Calcd for C23H26O4Na [M þ Na]þ 389.1729; found
389.1728.
115.4,118.7, 120.8,123.6,126.1, 127.3, 128.6,130.5,132.0, 132.2,133.1,
134.5, 136.5, 151.4, 153.5, 205.2. IR (KBr, cmꢀ1) 3366, 2917, 1673.
HRMS (ESI) m/z: Calcd for C20H17BrO3Na [M þ Na]þ 407.0259;
found 407.0259.
4.2.23. 1,8-Bis(allyloxy)-3-methylanthracene-9, 10-dione (2e)
Yellow solid. Yield 80%. mp: 106e107 ꢃC. 1H NMR (400 MHz,
CDCl3) d (ppm): 2.45 (s, 3H, AreCH3), 4.73e4.77 (m, 4H, OCH2), 5.35
4.2.17. 1-(8-(3-Chlorobenzyloxy)-1-hydroxy-3-methylnaphthalen-
2-yl)ethanone (1i)
White solid. Yield 63%. mp: 93e95 ꢃC. 1H NMR (400 MHz, CDCl3)
(dd, 2H, J ¼ 10.64,1.32 Hz), 5.63 (dd, 2H, J ¼ 15.6,1.64 Hz), 6.09e6.13
(m, 2H, CH), 7.09 (s, 1H, H-2), 7.28 (d, 1H, J ¼ 8.0 Hz, H-7), 7.58 (t, 1H,
J ¼ 7.76 Hz, H-6), 7.66 (s, 1H, H-4), 7.84 (dd, 1H, J ¼ 7.68, 0.88 Hz, H-
d
(ppm): 2.37 (s, 3H, AreCH3), 2.61 (s, 3H, COCH3), 5.24 (s, 2H,
OCH2), 6.80 (dd, 1H, J ¼ 6.64, 2.0 Hz, H-7), 7.12 (s, 1H, H-4), 7.27e
7.47 (m, 6H, AreH), 9.66 (s, 1H, OH). 13C NMR (100 MHz, CDCl3)
d:
5). 13C NMR (100 MHz, CDCl3)
d: 22.0, 70.0, 117.6, 119.2, 119.8, 120.6,
19.9, 32.2, 70.9, 105.4, 113.3, 119.8, 121.6, 124.9, 125.9, 126.9, 128.0,
129.1, 130.4, 134.2, 134.9, 136.7, 137.0, 152.1, 155.4, 205.4. IR (KBr,
cmꢀ1) 3330, 2930, 1672. HRMS (ESI) m/z: Calcd for C20H17ClO3Na
[M þ Na]þ 363.0764; found 363.0766.
122.2, 124.5, 132.5, 133.4, 133.6, 134.6, 134.9, 144.7, 158.3, 158.5,
182.0,184.3. IR (KBr, cmꢀ1) 2923, 2855,1669,1601,1586,1452,1236,
HRMS (ESI) m/z: Calcd for C21H18O4Na [M þ Na]þ 357.1103; found
357.1106.
4.2.18. 1-(1-(3-Chlorobenzyloxy)-8-hydroxy-3-methylnaphthalen-
2-yl)ethanone (1i0)
4.2.24. 1,8-Bis(benzyloxy)-3-methylanthracene-9,10-dione (2f)
Yellow solid. Yield 94%. mp: 183e185 ꢃC. 1H NMR (400 MHz,
CDCl3) d (ppm): 2.45 (s, 3H, AreCH3), 5.31 (s, 4H, OCH2), 7.16 (s, 1H,
White solid. Yield 30%. mp: 78e80 ꢃC. 1H NMR (400 MHz, CDCl3)
d
(ppm): 2.40 (s, 3H, AreCH3), 2.66 (s, 3H, COCH3), 4.97 (s, 2H,
OCH2), 6.90 (dd,1H, J ¼ 6.12, 2.35 Hz, H-7), 7.31e7.48 (m, 7H, AreH),
8.99 (s, 1H, OH). 13C NMR (100 MHz, CDCl3)
: 19.0, 32.9, 70.7, 107.7,
H-2), 7.32e7.43 (m, 7H, AreH), 7.59 (t, 1H, J ¼ 8.16 Hz, H-6), 7.64e
7.69 (m, 5H, AreH), 7.86 (dd, 1H, J ¼ 7.72, 0.80 Hz, H-5). 13C NMR
d
(100 MHz, CDCl3) d: 22.0, 71.1, 119.4, 120.1, 120.3, 120.9, 122.5, 124.8,
110.7, 118.8, 121.1, 125.0, 125.8, 127.0, 127.5, 127.8, 128.7, 129.0, 129.4,
130.2, 136.5, 150.7, 153.4, 205.4. IR (KBr, cmꢀ1) 3362, 2915, 1690.
HRMS (ESI) m/z: Calcd for C20H17ClO3Na [M þ Na]þ 363.0764; found
363.0766.
126.7, 127.8, 127.8, 128.5, 133.5, 134.6, 134.9, 136.6, 144.8, 158.2,
158.5, 182.0, 184.2. IR (KBr, cmꢀ1) 2922, 2858, 1671, 1600, 1321,
1238, HRMS (ESI) m/z: Calcd for C29H22O4Na [M þ Na]þ 457.1416;
found 457.1414.
4.2.19. 1,8-Dimethoxy-3-methylanthracene-9,10-dione (2a)
4.2.25. 1,8-Bis(3-chlorobenzyloxy)-3-methylanthracene-9, 10-dione
(2g)
Yellow solid. Yield 89%. mp: 189e190 ꢃC. 1H NMR (400 MHz,
Yellow solid. Yield 70%. mp: 190e192 ꢃC. 1H NMR (400 MHz,
CDCl3) d (ppm): 2.45 (s, 3H, AreCH3), 3.96 (s, 3H, OCH3), 3.98 (s, 3H,
OCH3), 7.08 (s, 1H, H-2), 7.28 (d, 1H, J ¼ 8.76 Hz, H-7), 7.58e7.62 (m,
CDCl3) d (ppm): 2.45 (s, 3H, AreCH3), 5.26 (s, 4H, OCH2), 7.12 (s, 1H,
2H, H-4, H-6), 7.80 (d, 1H, J ¼ 7.64 Hz, H-5). 13C NMR (100 MHz,
H-2), 7.27e7.37 (m, 5H, AreH), 7.58e7.62 (m, 5H, AreH), 7.7 (s, 1H,
H-4), 7.88 (dd, 1H, J ¼ 7.68, 0.88 Hz, H-5). 13C NMR (100 MHz, CDCl3)
CDCl3) d: 22.1, 56.4, 118.0, 118.6, 118.8, 119.4, 121.5, 123.9, 133.7,
134.4, 134.7, 145.0, 159.4, 159.6, 182.4, 184.2. IR (KBr, cmꢀ1) 2925,
2854, 1662, 1602, 1236. HRMS (ESI) m/z: Calcd for C17H14O4Na
[M þ Na]þ 305.0790; found 305.0790.
d: 22.0, 70.5, 119.8, 120.4, 120.5, 120.9, 122.4, 124.7, 124.9, 125.0,
126.8, 126.9, 127.9, 128.0, 130.0, 133.7, 134.4, 134.6, 134.9, 138.6,
138.7, 145.1, 158.0, 158.2, 181.9, 183.9. IR (KBr, cmꢀ1) 2922, 2869,
1670, 1601, 1321, 1237. HRMS (ESI) m/z: Calcd for C29H20Cl2O4Na
[M þ Na]þ 525.0636; found 525.0634.
4.2.20. 1,8-Diethoxy-3-methylanthracene-9,10-dione (2b)
Yellow solid. Yield 73%. mp: 118e119 ꢃC. 1H NMR (400 MHz,
CDCl3)
d
(ppm): 1.52 (t, 6H, J ¼ 7.0 Hz, CH3), 2.43 (s, 3H, AreCH3),
4.2.26. 1,8-Bis(4-iodobenzyloxy)-3-methylanthracene-9, 10-dione
(2h)
4.17e4.23 (m, 4H, OCH2), 7.07 (s,1H, H-2), 7.26 (d,1H, J ¼ 8.76 Hz, H-
7), 7.54e7.61 (m, 2H, H-4, H-6), 7.79 (dd, 1H, J ¼ 7.64, 1.0 Hz, H-5).
Yellow solid. Yield 87%. mp: 250e252 ꢃC. 1H NMR (400 MHz,
13C NMR (100 MHz, CDCl3)
d: 14.6, 14.7, 22.0, 65.3, 118.9, 119.5,
CDCl3) d (ppm): 2.46 (s, 3H, AreCH3), 5.22 (s, 4H, OCH2), 7.13 (s, 1H,
120.2, 122.2, 124.2, 133.5, 134.5, 134.8, 144.8, 158.8, 159.0, 182.3,
184.4. IR (KBr, cmꢀ1) 2926, 2855, 1669, 1601, 1456, 1236. HRMS (ESI)
m/z: Calcd for C19H18O4Na [M þ Na]þ 333.1103; found 333.1103.
H-2), 7.30 (d, 1H, J ¼ 8.20, H-7), 7.39e7.42 (m, 4H, AreH), 7.61 (t, 1H,
J ¼ 8.0 Hz, H-6), 7.70e7.75 (m, 5H, AreH), 7.88 (d, 1H, J ¼ 7.56 Hz, H-
5). 13C NMR (100 MHz, CDCl3)
d: 22.1, 70.5, 114.0, 119.7, 120.1, 120.3,