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1095
and H-8), 8.72 (bs, 1H, NHH), 8.87 (bs, 1N, NHH),
5.10. 1-Hydroxy-3-[3-(tert-butylamino)-2-
hydroxypropoxy]-9,10-anthraquinone
hydrochloride·1/2 H2O (13)
12.75 (s, 1H, OH-1); 13C-NMR (DMSO-d6) l11.5
(CH3), 20.7 (CH2CH3), 51.0 (NH2CH2), 51.1
(CHOHCH2NH2), 66.7 (CHOH), 72.0 (OCH2), 108.3
(C-2), 109.0 (C-4), 128.1 (C-8), 128.5 (C-5), 135.0 (C-8a
and C-10a), 135.9 (C-7), 136.0 (C-6), 136.9 (C-4a), 166.8
(C-1), 181.6 (C-10), 186.3 (C-9); MS m/z 355 (M+, 2).
Yellow powder: IR (KBr) 3335, 1681, 1636 cm−1
1H-NMR (DMSO-d6) l1.33 [s, 9H, C(CH3)3], 2.93–3.00
;
(m, 1H, CHHNH2), 3.14–3.19 (m, 1H, CHHNH2),
4.16–4.20 (m, 1H, CHOH), 4.23–4.26 (m, 1H, OCH2),
6.00 (bs, 1H, CHOH), 6.90 (d, J=2.4 Hz, 1H, H-2),
7.23 (d, J=2.4 Hz, 1H, H-4), 7.89–7.96 (m, 2H, H-6
and H-7), 8.14–8.21 (m, 2H, H-5 and H-8), 8.55 (bs,
5.8. 1-Hydroxy-3-[3-(cyclopropylamino)-2-
hydroxypropoxy]-9,10-anthraquinone·hydrochloride (11)
1H, CH2NNHH), 8.94 (bs, 1H, CH2NHH), 12.74 (s,
1H, OH-1); 13C-NMR (DMSO-d6) l25.0 (CH3×3),
43.8 (CH2NH2), 56.5 [C(CH3)3], 65.2 (CHOH), 70.6
(OCH2), 106.8 (C-2), 107.7 (C-4), 110.4 (C-9a), 126.5
(C-8), 126.9 (C-5), 132.9 (C-8a and C-10a), 134.6 (C-4a),
134.7 (C-7), 134.8 (C-6), 164.6 (C-1), 165.0 (C-3), 181.6
(C-10), 186.3 (C-9); MS m/z 369 (M+, 1).
Yellow powder: IR (KBr) 3465, 1691, 1631 cm−1
;
1H-NMR (DMSO-d6) l 0.75–0.93 (m, 4H, CH2 in the
cyclopropyl ring), 2.76 (bs, 1H, CH in the cyclopropyl
ring), 3.09–3.14 (m, 1H, CHHNH), 3.24–3.7 (m, 1H,
CHHNH), 4.16–4.25 (m, 3H, OCH2 and CHOH), 5.98
(s, 1H, CHOH), 6.94 (d, J=2.4 Hz, 1H, H-2), 7.27 (d,
J=2.4 Hz, 1H, H-4), 7.91–7.98 (m, 2H, H-6 and H-7),
8.18–8.25 (m, 2H, H-5 and H-8), 8.91 (bs, 2H, NH2),
5.11. 1-Hydroxy-3-[3-(n-butylamino)-2-
hydroxypropoxy]-9,10-anthraquinone hydrochloride (14)
12.78 (s, 1H, OH-1); 13C-NMR (DMSO-d6) l3.1 and 3.2
(CH2 in the cyclopropyl ring), 30.0 (CH in the cyclo-
propyl ring), 50.0 (CH2NH2), 64.5 (CHOH), 70.7
(OCH2), 106.8 (C-2), 107.8 (C-4), 110.4 (C-9a), 126.5
(C-8), 127.0 (C-5), 132.9 (C-8a and C-10a), 134.7 (C-4a),
134.8 (C-7), 134.9 (C-6), 164.6 (C-1), 165.0 (C-3), 181.6
(C-10), 186.3 (C-9); MS m/z 353 (M+, 3).
Yellow powder: IR (KBr) 3445, 1691, 1636 cm−1
;
1H-NMR (DMSO-d6) l 0.90 (t, J=7.3 Hz, 3H, CH3),
1.24–1.43 (m, 2H, CH2CH3), 1.56–1.68 (m, 2H,
NH2CH2CH2), 2.87–3.00 (m, 2H, NH2CH2CH2), 3.08–
3.33 (m, 2H, CH2NH2), 4.17–4.20 (m, 2H, OCH2),
4.25–4.31 (m, 1H, CHOH), 5.97 (bs, 1H, CHOH), 6.91
(d, J=2.6 Hz, 1H, H-2), 7.23 (d, J=2.6 Hz, 1H, H-4),
7.91–7.99 (m, 2H, H-6 and H-7), 8.14–8.25 (m, 2H, H-5
5.9. 1-Hydroxy-3-[3-(1-methylpropylamino)-2-
hydroxypropoxy]-9,10-anthraquinone
hydrochloride·1/3 H2O (12)
and H-8), 8.75 (bs, 1H, NHH), 8.91 (bs, 1H, NHH),
12.75 (s, 1H, OH-1); 13C-NMR (DMSO-d6) l13.5
(CH3), 19.3 (CH2CH3), 27.3 (NHCH2CH2), 47.0
(CH2NH2), 49.1 (NHCH2CH2), 64.6 (CHOH), 70.7
(OCH2), 106.8 (C-2), 107.8 (C-4), 110.4 (C-9a), 126.5
(C-8), 126.9 (C-5), 132.9 (C-8a and C-10a), 134.7 (C-4a
and C-7), 134.8 (C-6), 164.6 (C-1), 165.0 (C-3), 181.6
(C-10), 186.3 (C-9); MS m/z 369 (M+, 3).
Yellow powder: IR (KBr) 3435, 1705, 1626 cm−1
;
1H-NMR (DMSO-d6) l 0.91 (t, J=7.6 Hz, 3H,
CH2CH3), 1.27 (d, J=6 Hz, 3H, CHCH3), 1.47–1.57
(m, 1H, CHHCH3), 1.83–1.89 (m, 1H, CHHCH3),
2.99–3.06 (m, 1H, CHCH3), 3.12–3.21 (m, 2H,
CH2NH2), 4.12–4.20 (m, 2H, OCH2), 4.28–4.36 (m, 1H,
CHOH), 6.01 (s, 1H, CHOH), 6.78 (d, J=2.8 Hz, 1H,
H-2), 7.08 (d, J=2.8 Hz, 1H, H-4), 7.84–7.91 (m, 2H,
H-6 and H-7), 8.05–8.11 (m, 2H, H-5 and H-8), 8.74
5.12. 1-Hydroxy-3-[3-(cyclohexylamino)-2-
hydroxypropoxy]-9,10-anthraquinone
hydrochloride·1/3 H2O (15)
(bs, 1H, NHH) or 8.81 (bs, 1H, NHH), 9.09 (bs, 1H,
NHH) or 9.21 (bs, 1H, NHH), 12.64 (s, 1H, OH-1);
13C-NMR (DMSO-d6) l9.7 (CH2CH3), 14.9 (CHCH3),
25.0 (CH2CH3), 46.5 (CH2NH), 55.0 (CH), 64.8
(CHOH), 70.6 (OCH2), 106.7 (C-2), 107.7 (C-4),
110.2 (C-9a), 126.3 (C-8), 126.8 (C-5), 132.7 (C-8a and
C-10a), 134.4 (C-4a), 134.6 (C-7), 134.7 (C-6), 164.5
(C-1), 164.9 (C-3), 181.3 (C-10), 186.1 (C-9); MS m/z
369 (M+, 2).
Yellow powder: IR (KBr) 3475, 1686, 1616 cm−1
;
1H-NMR (CD3OD) l1.29–1.47 (m, 6H, CH2×3 in the
cyclohexane ring), 1.87–2.19 [m, 4H, CH(CH2)2 in the
cyclohexane ring], 3.13–3.24 (m, 3H, CH2NH2 and CH
in the cyclohexane ring), 4.19–4.21 (m, 2H, OCH2),
4.24–4.30 (m, 1H, CHOH), 6.86 (d, J=2.6 Hz, 1H,
H-2), 7.40 (d, J=2.6 Hz, 1H, H-4), 7.88–7.90 (m, 2H,