6940 Journal of Medicinal Chemistry, 2009, Vol. 52, No. 21
Pizzirani et al.
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(2β,6β)-2-(4-Hydroxyphenyl)-6-phenylspiro[cyclohexane-1,20-
indene]-10,30,4-trione 8. 4-Hydroxybenzaldehyde 18 (0.12 g, 1.0
mmol), 1,3-indandione 21, and (E)-4-phenyl-3-buten-2-one 23
were allowed to react according to the described general proce-
dure, and the crude Diels-Alder product was purified on silica,
eluting with 8:2 petroleum ether/EtOAc. Yield, 0.19 g (51%);
white solid (mp 204 °C); 1H NMR (CDCl3, 300 MHz) δ
2.61-2.68 (m, 2H), 3.70-3.87 (m, 4H), 6.50 (d, J = 9 Hz,
2H), 6.88 (d, J = 9 Hz, 2H), 6.95-7.02 (m, 5H), 7.42-7.53 (m,
3H), 7.66 (d, J = 7.8 Hz, 1H); 13CNMR (CDCl3, 75 MHz,
DEPT) δ 43.3 (CH2), 43.6 (CH2), 47.9 (CH), 48.6 (CH), 62.2 (C),
115.2 (CH), 122.1 (CH), 122.4 (CH), 127.6 (CH), 127.9 (CH),
128.2 (CH), 128.3 (CH), 129.2 (CH), 135.4 (CH), 137.2 (C),
141.9 (C), 142.7 (C), 155.2 (C), 202.3 (C, CdO), 203.7 (C, CdO),
209.4 (C, CdO); IR νmax (Nujol) cm-1 1174, 1255, 1376, 1462,
1516, 1591, 1613, 1694, 1732, 3498. Anal. (C26H20O4) C, H.
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Acknowledgment. This work was supported by
PRIN2006 Project Grant from MIUR, Italy.
a
Note Added after ASAP Publication. This paper was pub-
lished ASAP on September 18, 2009 with an error in the Results
and Discussion section. The revised version was published on
October 1, 2009.
Supporting Information Available: Synthesis of (E)-4-substi-
tuted-3-buten-2-ones (24, 25); physical and spectroscopic data
for derivatives 7-13, 24, 25; detailed biological protocols;
Figure A, B. This material is available free of charge via the
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