Antiproliferative activity of some 1,4-dimethylcarbazoles on cells that express estrogen receptors: part I

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• (1a) White solid, mp 174°C. IR (KBr) (cm-1): 3517, 3415, 1461, 1165, 847, 809, 543. 1HNMR (DMSO-d6): δ 2.50 (s, 3H, CH3), 2.61 (s, 3H, CH3); 6.83 (d, J = 7.36 Hz, 1H, Ar); 6.95 (d, J = 8.56 Hz, 1H, Ar); 7.08 (d, J = 7.36 Hz, 1H, Ar); 7.40 (d, J = 8.56 Hz, 1H, Ar); 7.53 (s, 1H, Ar); 9.12 (br, 1H, OH); 10.88 (s, 1H, NH). MS (ESI+): 212 (M+ +1).
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• (1b) White solid, mp 150°C. IR (KBr) (cm-1): 3406, 2959, 1481, 1210, 1045, 812, 545. 1H NMR (DMSO-d6): δ 2.62 (s, 3H, CH3), 2.69 (s, 3H, CH3), 3.90 (s, 3H, OCH3), 6.85 (d, J = 7.08 Hz, 1H, Ar); 7.09 (d, J = 8.28 Hz, 2H, Ar), 7.48 (d, J = 8.56 Hz, 1H, Ar), 7.64 (s, 1H, Ar), 11.01 (br, 1H, NH). MS (ESI+): 226 (M+ +1), 224 (M+ -1).
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• (1c) White solid, mp 266°C. IR (KBr) (cm-1): 3337, 1702, 1615, 1430, 1290, 1122, 989, 803, 764, 735, 557. 1H NMR (DMSO-d6): δ 2.52 (s, 3H, CH3), 2.71 (s, 3H, CH3), 3.84 (s, 3H, OCH3), 6.89 (d, J = 7.84 Hz, 1H, Ar); 7.11 (d, J = 7.32 Hz, 1H, Ar), 7.55 (d, J = 8.08 Hz, 1H, Ar), 7.98 (dd, J1 = 1.48 Hz, J2 = 8.56 Hz, 1H, Ar), 8.67 (s, 1H, Ar), 11.62 (s, 1H, NH). MS (ESI+): 254 (M+ +1).
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• (1d) White solid, mp 253°C. IR (KBr) (cm-1): 3339, 1705, 1618, 1430, 1295, 1129, 990, 806, 765, 738, 560. 1H NMR (DMSO-d6): δ 1.67 (s, 3H, CH3), 2.53 (s, 3H, CH3), 2.80 (s, 3H, CH2CH3), 4.30-4.60 (m, 2H, OCH2), 6.95 (d, J = 7.50 Hz, 1H, Ar); 7.16 (d, J = 7.20 Hz, 1H, Ar), 7.55 (d, J = 8.70 Hz, 1H, Ar), 8.04 (d, J = 8.70 Hz, 1H, Ar), 8.72 (s, 1H, Ar), 11.59 (br, 1H, NH). MS (ESI+): 268 (M+ +1).
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• (1e) White solid, mp 130°C. IR (KBr) (cm-1): 3396, 1744, 1462, 1253, 1181, 1002, 811, 780, 552. 1H NMR (DMSO-d6): δ 1.32-1.40 (t, 3H, CH2CH3), 2.57 (s, 3H, CH3), 2.78 (s, 3H, CH3), 4.28–4.35 (q, 2H, CH2CH3), 6.91 (d, 1H, J = 7.08 Hz, Ar), 7.16 (d, 1H, J = 7.32 Hz, Ar), 7.29 (dd, 1H, J1 = 1.72 Hz, J2 = 8.56 Hz, Ar), 7.58 (d, 1H, J = 8.56 Hz, Ar), 7.94 (s, 1H, Ar), 11.36 (s, 1H, NH). MS (ESI+): 284 (M+ +1).
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• (1f) White solid, mp 202°C. IR (KBr) (cm-1): 3415, 1587, 1460, 1165, 809, 543. 1H NMR (CDCl3): δ 8.23 (d, J = 1.96 Hz, 1H, Ar); 7.52 (dd, J = 8.80 Hz, 1H, Ar); 7.23 (d, J = 8.80 Hz, 1H, Ar); 7.07 (d, J = 7.32 Hz, 1H, Ar); 6.88 (d, J = 7.32 Hz, 1H, Ar); 4.07 (s, 3H, NCH3); 2.80 (s, 3H, CH3); 2.78 (s, 3H, CH3). MS (ESI+): 226 (M+ +1).
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• (1g) White solid, mp 205°C. IR (KBr) (cm-1): 3410, 1701, 1449, 1329, 1157, 807. 1HNMR (CDCl3): δ 1.64 (s, 9H, CH3); 2.43 (s, 3H, CH3); 2.74 (s, 3H, CH3); 6.91 (d, J = 8.56 Hz, 1H, Ar); 6.98 (d, J = 7.32 Hz, 1H Ar,); 7.09 (d, J = 7.32 Hz, 1H, Ar); 7.46 (s, 1H, OH); 7.63 (d, J = 8.56 Hz, 1H, Ar); 7.85 (s, 1H, Ar). MS (EI) m/z (%): 311 (M+, 15), 255 (48) (M+, -tBu), 211 (100) (M+, -CO2tBu).
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