Helvetica Chimica Acta Vol. 86 (2003)
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2-{[(Dibenzo[b,d]furan-2-yl)oxy]methyl}-5-hydroxy-1-methyl-1H-pyridin-4-one (10d). Yield: 86% (from
8i). M.p. 107 1098. 1H-NMR (DMSO): 4.07 (s, MeN); 4.15 (br. s, OH); 5.44 (s, CH2O); 7.19 7.17 (m, 7 arom.
H); 8.15 (m, 1 arom. H); 8.29 (s, HÀC(6)). 13C-NMR (DMSO): 42.46; 65.65; 106.39; 111.78; 112.43; 116.26;
121.27; 122.97; 123.68; 124.30; 127.81; 128.50; 128.65; 132.05; 144.83; 150.70; 153.52; 156.24; 161.91. Anal. calc.
for C19H15NO4: C 71.02, H 4.71, N 4.36; found: C 69.98, H 4.80, N 4.26.
5-Hydroxy-1-methyl-2-{[(9-oxo-9H-fluoren-2-yl)oxy]methyl}-1H-pyridin-4-one (10e). Yield: 72% (from
1
8j). M.p. 248 2518. H-NMR (DMSO): 3.75 (br. s, OH); 4.05 (s, MeN); 5.45 (s, CH2O); 7.34 (m, 3 arom. H);
7.47 (s, HÀC(3)); 7.57 (m, 2 arom. H); 7.75 (m, 2 arom. H); 8.34 (s, HÀC(6)). 13C-NMR (DMSO): 42.80; 65.01;
110.64; 112.18; 120.69; 121.66; 122.55; 124.05; 128.58; 133.07; 133.40; 135.14; 135.60; 137.60; 144.04; 144.50;
144.65; 158.40; 160.69; 192.79. Anal. calc. for C20H15NO4 ¥ 0.8H2O: C 69.07, H 4.81, N 4.03; found: C 69.11, H
4.86, N 4.08.
5-Hydroxy-1-methyl-2-{[(9-oxo-9H-xanthen-3-yl)o xy]methyl}-1H-pyridin-4-one (10f). Yield: 95% (from
8k). M.p. 257 2598. 1H-NMR (DMSO): 3.85 (br. s, OH); 4.08 (s, MeN); 5.57 (s, CH2O); 7.24 (dd, J 8.8, 2.2,
HÀC(2')); 7.45 8.21 (m, 7 arom. H); 8.37 (s, HÀC(6)). 13C-NMR (DMSO): 43.18; 65.42; 102.45; 107.09;
112.33; 114.31; 116.15; 118.21; 121.47; 124.79; 126.23; 128.22; 133.57; 135.56; 144.42; 144.80; 155.91; 157.64;
162.79; 175.22. Anal. calc. for C20H15NO5: C 68.76, H 4.33, N 4.01; found: C 68.71, H 4.33, N 4.06.
2-[(1,2-Dihydro-5-hydroxy-1-methyl-4-oxopyridin-2-yl)methoxy]anthraquinone (10g). Yield: 83% (from
8l). M.p. 2128 (dec). 1H-NMR (DMSO): 3.75 (br. s, OH); 4.08 (s, MeN); 5.61 (s, CH2O); 7.47 (s, HÀC(3')); 7.63
(dd, J 8.8, 2.6, HÀC(3)); 7.83 (d, J 2.6, HÀC(1)); 7.94 (m, 2 arom. H); 8.22 (m, 3 arom. H); 8.32
(s, HÀC(6')). 13C-NMR (DMSO): 43.05; 65.40; 107.09; 111.78; 112.99; 121.78; 127.02; 127.07; 127.71; 129.94;
133.07; 133.32; 134.62; 135.03; 135.46; 144.17; 145.07; 161.47; 162.05; 181.63; 182.55. Anal. calc. for C21H15NO5: C
69.80, H 4.18, N 3.88; found: C 69.72, H 4.22, N 3.91.
Financial support of this work by the National Science Council of the Republic of China (NSC 90-2113-M-
037-014) is gratefully acknowledged. We also thank National Cancer Institute (NCI) of the United States for the
anticancer screenings and the National Center for High-Performance Computing for providing computer
resources and chemical database services.
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