H.-Q. Li et al. / European Journal of Medicinal Chemistry 44 (2009) 2246e2251
2249
[M þ H]þ). Anal. Calcd for C14H13NO5: C 61.09, H 4.76, N
4.2.7. 1-(2,4-Dihydroxyphenyl)-2-(4-methoxyphenyl)
ethanone oxime (4a)
5.09%; found: C 61.15, H 4.73, N 5.16%.
Yellow solid, m.p. 193e194 ꢁC; 1H NMR (500 MHz,
DMSO-d6): 3.76 (s, 3H), 4.08 (dd, J ¼ 3.5, 9 Hz, 2H), 6.28
(d, J ¼ 9 Hz, 1H), 6.42 (dd, J ¼ 2, 9 Hz, 1H), 6.87 (d,
J ¼ 9 Hz, 2H), 7.21 (d, J ¼ 9 Hz, 2H), 7.87 (d, J ¼ 9 Hz,
1H), 10.45 (s, 1H), 12.21 (s, 1H), 12.56 (s, 1H). ESI-MS:
274.1 (C15H15NO4 [M þ H]þ). Anal. Calcd for C15H15NO4:
C 65.92, H 5.53, N 5.13%; found: C 65.97, H 5.45, N 5.21%.
4.2.2. 4-(1-Amino-2-(4-hydroxyphenyl)ethyl)benzene-
1,2,3-triol (1b)
1
Colorless oil, H NMR (500 MHz, DMSO-d6): 1.81 (br s,
2H), 2.98 (dd, J ¼ 3.5, 9 Hz, 2H), 4.07 (d, J ¼ 10.5 Hz, 1H),
6.39 (d, J ¼ 9 Hz, 1H), 6.65 (d, J ¼ 8 Hz, 2H), 7.02 (d,
J ¼ 9 Hz, 1H), 7.17 (d, J ¼ 8 Hz, 2H), 8.71 (s, 1H), 9.45 (s,
1H), 10.11 (s, 1H), 12.45 (s, 1H). ESI-MS: 262.1
(C14H15NO4 [M þ H]þ). Anal. Calcd for C14H15NO4: C
64.36, H 5.79, N 5.36%; found: C 64.39, H5.73, N 5.41%.
4.2.8. 4-(1-Amino-2-(4-methoxyphenyl)ethyl)benzene-
1,3-diol (4b)
1
Colorless oil, H NMR (500 MHz, DMSO-d6): 1.81 (br s,
2H), 2.98 (dd, J ¼ 3.5, 9 Hz, 2H), 3.76 (s, 3H), 4.11 (d,
J ¼ 10.5 Hz, 1H), 6.26 (d, J ¼ 9 Hz, 1H), 6.42 (dd, J ¼ 2,
9 Hz, 1H), 6.87 (d, J ¼ 9 Hz, 2H), 7.17 (d, J ¼ 9 Hz, 2H),
7.76 (d, J ¼ 9 Hz, 1H), 10.54 (s, 1H), 12.11 (s, 1H). ESI-
MS: 258.4 (C15H17NO3 [M ꢃ H]þ). Anal. Calcd for
C15H17NO3: C 69.48, H 6.61, N 5.40%; found: C 69.41, H
6.65, N 5.31%.
4.2.3. 2-(4-Fluorophenyl)-1-(2,3,4-trihydroxyphenyl)
ethanone oxime (2a)
Yellow solid, m.p. 172e175 ꢁC; 1H NMR (500 MHz,
DMSO-d6): 3.93 (dd, J ¼ 3.5, 9 Hz, 2H), 6.37 (d, J ¼ 9 Hz,
1H), 6.92 (d, J ¼ 8 Hz, 2H), 7.15 (d, J ¼ 8 Hz, 2H), 7.34 (d,
J ¼ 9 Hz, 1H), 8.84 (s, 1H), 10.21 (s, 1H), 12.56 (s, 1H),
12.92 (s, 1H). ESI-MS: 278.2 (C14H12FNO4 [M þ H]þ).
Anal. Calcd for C14H12FNO4: C 60.65, H 4.36, F 6.85, N
5.05%; found: C 60.56, H 4.25, F 6.77, N 5.11%.
4.2.9. 1-(2,4-Dihydroxyphenyl)-2-(4-nitrophenyl)
ethanone oxime (5a)
Yellow solid, m.p. 167e169 ꢁC; 1H NMR (500 MHz,
DMSO-d6): 4.11 (dd, J ¼ 3.5, 9 Hz, 2H), 6.26 (s, 1H), 6.42
(d, J ¼ 9 Hz, 1H), 7.64 (d, J ¼ 8 Hz, 2H), 7.94 (d, J ¼ 9 Hz,
1H), 9.19 (d, J ¼ 8 Hz, 2H), 10.65 (s, 1H), 12.25 (s, 1H),
12.64 (s, 1H). ESI-MS: 289.1 (C14H12N2O5 [M þ H]þ).
Anal. Calcd for C15H15N2O5: C 58.33, H 4.20, N 9.72%;
found: C 58.25, H 4.23, N 9.61%.
4.2.4. 4-(1-Amino-2-(4-fluorophenyl)ethyl)benzene-
1,2,3-triol (2b)
1
Colorless oil, H NMR (500 MHz, DMSO-d6): 1.83 (br s,
2H), 2.85 (dd, J ¼ 3.5, 9 Hz, 2H), 4.12 (d, J ¼ 10.5 Hz, 1H),
6.36 (d, J ¼ 9 Hz, 1H), 6.92 (d, J ¼ 8 Hz, 2H), 7.17 (d,
J ¼ 8 Hz, 2H), 7.23 (d, J ¼ 9 Hz, 1H), 8.92 (s, 1H), 10.11 (s,
1H), 12.21 (s, 1H). ESI-MS: 264.1 (C14H14FNO3 [M þ H]þ).
Anal. Calcd for C14H14FNO3: C 63.87, H 5.36, F 7.22, N
5.32%; found: C 63.83, H 5.31, F 7.27, N 5.38%.
4.2.10. 4-(1-Amino-2-(4-nitrophenyl)ethyl)benzene-1,
3-diol (5b)
1
Colorless oil, H NMR (500 MHz, DMSO-d6): 1.82 (br s,
2H), 2.98 (dd, J ¼ 3.5, 9 Hz, 2H), 4.03 (d, J ¼ 10.5 Hz, 1H),
6.28 (d, J ¼ 9 Hz, 1H), 6.42 (d, J ¼ 9 Hz, 1H), 7.56 (d,
J ¼ 8 Hz, 2H), 7.91 (d, J ¼ 9 Hz, 1H), 9.08 (d, J ¼ 8 Hz,
2H), 10.76 (s, 1H), 12.21 (s, 1H). ESI-MS: 275.1
(C14H14N2O4 [M þ H]þ). Anal. Calcd for C14H14N2O4: C
61.31, H 5.14, N 10.21%; found: C 61.38, H 5.11, N 10.26%.
4.2.5. 1-(2,4-Dihydroxyphenyl)-2-(4-fluorophenyl)
ethanone oxime (3a)
Yellow solid, m.p. 187e189 ꢁC; 1H NMR (500 MHz,
DMSO-d6): 4.13 (dd, J ¼ 3.5, 9 Hz, 2H), 6.24 (s, 1H), 6.39
(d, J ¼ 9 Hz, 1H), 6.90 (d, J ¼ 8 Hz, 2H), 7.08 (d, J ¼ 9 Hz,
2H), 7.88 (d, J ¼ 9 Hz, 1H), 9.29 (s, 1H), 10.65 (s, 1H),
12.64 (s, 1H). ESI-MS: 262.1 (C14H12FNO3 [M þ H]þ).
Anal. Calcd for C14H12FNO3: C 64.36, H 4.63, F 7.27, N
5.36%; found: C 64.19, H 4.77, F 7.33, N 5.41%.
4.2.11. 1-(3,4-Dihydroxyphenyl)-2-(4-hydroxyphenyl)
ethanone oxime (6a)
Brown solid, m.p. 231e233 ꢁC; 1H NMR (500 MHz,
DMSO-d6): 4.08 (dd, J ¼ 3.5, 9 Hz, 2H), 6.67 (d, J ¼ 8 Hz,
2H), 6.80 (d, J ¼ 1 Hz, 1H), 7.02 (d, J ¼ 8 Hz, 2H), 7.37 (s,
1H), 7.46 (d, J ¼ 8 Hz, 1H), 9.22 (s, 1H), 9.35 (s, 1H),
10.02 (s, 1H), 11.23 (s, 1H). ESI-MS: 260.1 (C14H13NO4
[M þ H]þ). Anal. Calcd for C14H13NO4: C 64.86, H 5.05, N
5.40%; found: C 64.78, H 5.11, N 5.46%.
4.2.6. 4-(1-Amino-2-(4-fluorophenyl)ethyl)benzene-
1,3-diol (3b)
1
Colorless oil, H NMR (500 MHz, DMSO-d6): 1.84 (br s,
2H), 2.78 (dd, J ¼ 3.5, 9 Hz, 2H), 4.03 (d, J ¼ 10.5 Hz, 1H),
6.24 (d, J ¼ 9 Hz, 1H), 6.42 (d, J ¼ 9 Hz, 1H), 6.87 (d,
J ¼ 8 Hz, 2H), 7.11 (d, J ¼ 9 Hz, 2H), 7.93 (d, J ¼ 9 Hz,
1H), 10.54 (s, 1H), 12.11 (s, 1H). ESI-MS: 248.2
(C14H14FNO2 [M þ H]þ). Anal. Calcd for C14H14FNO2: C
68.00, H 5.71, F 7.68, N 5.66%; found: C 68.09, H 5.77, F
7.63, N 5.61%.
4.2.12. 4-(1-Amino-2-(4-hydroxyphenyl)ethyl)benzene-1,
2-diol (6b)
1
Yellow oil, H NMR (500 MHz, DMSO-d6): 1.85 (br s,
2H), 3.02 (dd, J ¼ 3.5, 9 Hz, 2H), 4.03 (d, J ¼ 10.5 Hz, 1H),
6.56 (d, J ¼ 8 Hz, 2H), 6.73 (d, J ¼ 1 Hz, 1H), 7.05 (d,
J ¼ 8 Hz, 2H), 7.39 (s, 1H), 7.48 (d, J ¼ 8 Hz, 1H), 9.22