Medicinal Chemistry Research
114.29 (C, C-1′), 96.59 (CH, C-3′,5′), 94.11 (CH2, 4′-
OCH2O-), 93.99 (CH2, 2′,6′-OCH2O-), 55.96 (CH3, 4′-
OCH3), 55.77 (CH3, 2′,6′-OCH3); EIMS m/z: 406.0 [M]+.
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxychroman-4-one
(4d)
White solid; yield: 30%; mp 229–230 °C; IR (KBr) νmax
3,5,7-Trihydroxy-2-phenylchroman-4-one (4a)
3356, 2926, 2854, 1640, 1468, 1283, 1162, 1086, 996, 811,
1
777, 665 cm−1; H NMR (DMSO-d6, 400 MHz): δ = 11.89
White solid; yield: 40%; mp 177–180 °C; IR (KBr) νmax
(1H, s, OH-5), 10.80 (1H, s, OH-7), 9.02 (1H, s, OH-3′),
8.96 (1H, s, OH-4′), 6.85 (1H, s, H-2′), 6.75–6.70 (2H, m,
H-5′,6′), 5.86 (2H, dd, J = 29.2, 2.1 Hz, H-6,8), 5.74 (1H,
d, J = 6.2 Hz, OH-3), 4.96 (1H, d, J = 11.2 Hz, H-2), 4.48
(1H, dd, J = 11.2, 6.2 Hz, H-3); 13C NMR (DMSO-d6, 100
MHz): δ = 198.2 (C=O, C-4), 167.2 (C, C-7), 163.7 (C, C-
5), 163.0 (C, C-9), 146.2 (C, C-3′), 145.3 (C, C-4′), 128.4
(C, C-1′), 119.8 (CH, C-6′), 115.7 (CH, C-5′), 115.5 (CH,
C-2′), 100.9 (C, C-10), 96.4 (CH, C-6), 95.4 (CH, C-8),
83.4 (CH, C-2), 71.9 (CH, C-3); EIMS m/z: 305.1 [M]+.
1
3351, 2925, 1640, 1451, 1300, 1042, 820 cm−1; H NMR
(DMSO-d6, 400 MHz): δ = 11.91 (1H, s, OH-5), 10.88 (1H,
s, OH-7), 7.53 (2H, d, J = 5.7 Hz, H-2′,6′), 7.42 (3H, d,
J = 7.2 Hz, H-3′,4′,5′), 5.92 (2H, dd, J = 16.1, 2.1 Hz, H-
6,8), 5.88 (1H, d, J = 6.3 Hz, OH-3), 5.19 (1H, d, J = 11.4
Hz, H-2), 4.64 (1H, dd, J = 11.4, 6.0 Hz, H-3); 13C NMR
(DMSO-d6, 100 MHz): δ = 198.0 (C=O, C-4), 167.3 (C, C-
7), 163.8 (C, C-5), 162.91 (C, C-9), 137.7 (C, C-1′), 129.1
(CH, C-4′), 128.6 (C, C-3′,5′), 128.5 (C, C-2′,6′), 100.9 (C,
C-10), 96.6 (CH, C-6), 95.5 (CH, C-8), 83.3 (CH, C-2),
71.9 (CH, C-3); EIMS m/z: 272.0 [M]+.
3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-4-one
(4e)
3,5,7-Trihydroxy-2-(3-hydroxyphenyl)chroman-4-one (4b)
White solid; yield: 25%; mp 234–236 °C; IR (KBr) νmax
1
White solid; yield: 55%; mp 201–203 °C; IR (KBr) νmax
3335, 2911, 1640, 1465, 1288, 1094, 825 cm−1; H NMR
1
3333, 2913, 1637, 1442, 1280, 1037, 842 cm−1; H NMR
(DMSO-d6, 400 MHz): δ = 12.10 (1H, s, OH-5), 10.89 (1H,
s, OH-7), 9.45 (1H, s, OH-4′), 8.89 (1H, s, OH-3′), 8.86
(1H, s, OH-5′), 7.11 (2H, s, H-2′,6′), 5.89 (2H, dd, J = 9.8,
2.4 Hz, H-6, 8), 5.73 (1H, d, J = 6.1 Hz, OH-3), 5.01 (1H,
d, J = 11.2 Hz, H-2), 4.48 (1H, dd, J = 11.2, 6.2 Hz, H-3);
13C NMR (DMSO-d6, 100 MHz): δ = 197.9 (C, C-4), 167.2
(C, C-7), 164.8 (C, C-5), 164.2 (C, C-9), 158.0 (C, C-4′),
145.9 (C, C-3′), 133.8 (C, C-5′), 131.4 (C, C-1′), 116.5
(CH, -2′, 6′), 101.5 (C, C-10), 96.7 (CH, C-6), 96.1 (CH, C-
8), 81.9 (CH, C-2), 72.4 (CH, C-3); EIMS m/z: 320.2 [M]+.
(DMSO-d6, 400 MHz): δ = 12.02 (1H, s, OH-5), 10.91 (1H,
s, OH-7), 10.91 (1H, s, OH-3′), 7.14 (1H, t, J = 7.4 Hz, H-
5′), 7.02 (1H, d, J = 7.0 Hz, H-6′), 6.93–6.84 (2H, m, H-
2′,4′), 5.91 (2H, dd, J = 20.8 Hz, 1.4 Hz, H-6,8), 5.72 (1H,
d, J = 6.2 Hz, OH-3), 5.01 (1H, d, J = 11.6 Hz, H-2), 4.48
(1H, dd, J = 11.6 Hz, H-3); 13C NMR (DMSO-d6, 100
MHz): δ = 198.1 (C=O, C-4), 168.0 (C, C-7), 164.4 (C, C-
5), 163.6 (C, C-9), 158.7 (C, C-3′), 134.9 (CH, C-4′), 130.6
(C, C-1′), 119.9 (CH, C-6′), 116.0 (CH, C-5′), 115.5 (CH,
C-2′), 101.2 (C, C-10), 96.7 (CH, C-6), 96.0 (CH, C-8),
83.2 (CH, C-2), 72.6 (CH, C-3); EIMS m/z: 288.0 [M]+.
3,5,7-Trihydroxy-2-(3-methoxyphenyl)chroman-4-one (4f)
3,5,7-Trihydroxy-2-(4-hydroxyphenyl)chroman-4-one (4c)
White solid; yield: 37%; mp 134–136 °C; IR (KBr) νmax
1
3325, 2918, 1651, 1455, 1286, 1084, 817 cm−1; H NMR
White solid; yield: 35%; mp 219–220 °C; IR (KBr) νmax
(DMSO-d6, 400 MHz): δ = 11.93 (1H, s, OH-5), 10.98 (1H,
s, OH-7), 7.35 (1H, t, J = 7.8 Hz, H-5′), 7.12 (2H, d, J =
8.0 Hz, H-2′,6′), 6.97 (1H, d, J = 5.8 Hz, H-4′), 5.96 (2H, d,
J = 13.1 Hz, H-6,8), 5.88 (1H, s, OH-3), 5.17 (1H, d, J =
11.3 Hz, H-2), 4.65 (1H, d, J = 11.3 Hz, H-3), 3.79 (3H, s,
O-CH3); 13C NMR (DMSO-d6, 100 MHz): δ = 197.9
(C=O, C-4), 167.3 (C, C-7), 163.8 (C, C-5), 162.8 (C, C-9),
159.6 (C, C-3′), 139.2 (C, C-1′), 129.7 (CH, C-5′), 120.7
(CH, C-6′), 114.4 (CH, C-4′), 114.2 (CH, C-2′), 100.9 (C,
C-10), 96.6 (CH, C-6), 95.6 (CH, C-8), 83.3 (CH, C-2),
72.0 (CH, C-3), 55.5 (CH3, O-CH3); EIMS m/z: 302.0
[M]+.
1
3327, 2902, 1630, 1462, 1281, 1088, 813 cm−1; H NMR
(DMSO-d6, 400 MHz): δ = 11.92 (1H, s, OH-5), 10.84 (1H,
s, OH-7), 9.56 (1H, s, OH-4′), 7.32 (2H, d, J = 8.1 Hz, H-
2′,6′), 6.80 (2H, d, J = 8.1 Hz, H-3′,5′), 5.90 (2H, d, J =
21.4 Hz, H-6,8), 5.76 (1H, d, J = 6.1 Hz, OH-3), 5.06 (1H,
d, J = 11.3 Hz, H-2), 4.59 (1H, dd, J = 11.4, 5.6 Hz, H-3);
13C NMR (DMSO-d6, 100 MHz): δ = 198.3 (C=O, C-4),
167.2 (C, C-7), 163.7 (C, C-5), 163.0 (C, C-9), 158.2 (C, C-
4′), 129.9 (CH, C-2′,6′), 128.0 (C, C-1′), 115.3 (CH, C-
3′,5′), 100.9 (C, C-10), 96.5 (CH, C-6), 95.4 (CH, C-8),
83.1 (CH, C-2), 71.9 (CH, C-3); EIMS m/z: 288.2 [M]+.