RSC Advances
Paper
three crystals of 2,6-ditertbutyl-4-methylphenol dissolved in dry
toluene (2 mL), ushed the ask for 10 min with nitrogen gas.
Bioorg. Med. Chem., 2004, 12, 4393; (d) N. Vicker,
H. R. Lawrence, G. M. Allan, C. Bubert, A. Smith,
H. J. Tutill, A. Purohit, J. M. Day, M. F. Mahon, M. J. Reed
and B. V. L. Potter, ChemMedChem, 2006, 1, 464.
Added 6 mg of Pd-catalyst and again ush with N gas for 5 min.
2
ꢁ
Then, the mixture was stirred for 2 days at 100–110 C. Aer
completion of reaction, the solvent was evaporated under
reduced pressure, followed by washing with hexane to remove
excess tin derivative. Puried using silica gel column chroma-
tography using hexane : ethyl acetate (1 : 4) to obtain avones–
estradiol adducts in 60–70% yields.
9 (a)
M.
de
Angelis,
F.
Stossi,
M.
Waibel,
B. S. Katzenellenbogen and J. A. Katzenellenbogen, Bioorg.
Med. Chem., 2005, 13, 6529; (b) A. T. Vu, S. T. Cohn,
E. S. Manas, H. A. Harris and R. E. Mewshaw, Bioorg. Med.
Chem., 2005, 13, 6529; (c) A. T. Vu, S. T. Cohn, E. S. Manas,
H. A. Harris and R. E. Mewshaw, Bioorg. Med. Chem. Lett.,
2005, 15, 4520.
(Z)-5-Chloro-1-(1-(4-hydroxyphenyl)propylidene)-3-(4-(2-(piperi-
din-1-yl)ethoxy)phenyl)-2,3-dihydro-1H-inden-2-ol (5af). Light
ꢂ1
yellow semi solid; yield: 8%; IR nmax (KBr, cm ): 3431 (OH str), 10 M. M. Gottardis and V. C. Jordan, Cancer Res., 1988, 48, 5183.
2
1
8
4
951, 2880 (aromatic C–H str), 1608 (aromatic, C]C str), 1271, 11 K. Yao, E. S. Lee and D. J. Bentreme, Clin. Cancer Res., 2000,
1
109, 843, 729; H-NMR (CDCl
.0 Hz, 3H), 7.52–7.11 (m, 3H), 7.01–6.92 (m, 5H), 5.61 (s, 1H), 12 J. N. Ingle, D. J. Ahmann and S. J. Green, N. Engl. J. Med.,
.67 (d, J ¼ 2.0 Hz, 1H), 4.23 (d, J ¼ 2.0 Hz, 1H), 4.11 (t, J ¼ 2.5 1981, 304, 16.
3
, 500 MHz) d (ppm): 7.87 (t, J ¼
6, 2028.
Hz, 2H), 2.67–2.52 (m, 6H), 1.86 (q, J ¼ 7.0 Hz, 2H), 1.49–1.25 13 R. Chesworth, M. D. Wessel, L. Heyden, F. M. Mangano,
1
3
(
m, 6H), 0.68 (t, J ¼ 7.0 Hz, 3H); C (CDCl , 125 MHz) d (ppm):
M. Zawistoski, L. Gegnas, D. Galluzzo, B. Leer,
K. O. Cameron, J. Lu, B. Tickner, T. A. Castleberry,
D. N. Petersen, A. Brault, P. Pia Perry, O. Ng, T. A. Owen,
L. Pan, H. Z. Ke, T. A. Brown, D. D. Thompson and P. Da
Silva-Jardine, Bioorg. Med. Chem. Lett., 2005, 15, 5562.
14 A. K. Fink, J. Gurwitz, W. Rakowski, E. Guadagnoli and
R. A. Silliman, J. Clin. Oncol., 2004, 22, 3309.
3
1
1
7
60.12, 158.41, 144.87, 144.67, 140.10, 139.54, 136.22, 133.62,
31.50, 130.77, 129.64, 129.32, 124.36, 123.12, 117.69, 117.10,
3.19, 69.13, 58.10, 57.44, 52.85, 25.67, 23.83, 21.14, 11.10;
HRMS (ES-TOF) calcd for C31
03.2228.
3
H34ClNO 503.2227, found
5
1
5 T. L. Lash, M. P. Fox, J. L. Westrup, A. K. Fink and
R. A. Silliman, Breast Cancer Res. Treat., 2006, 99, 215.
Acknowledgements
Financial support and award of junior research fellowship by 16 E. A. Grunfeld, M. S. Hunter, P. Sikka and S. Mittal, Patient
the Department of Science and Technology (DST), New Delhi
and BRNS, BARC Mumbai, India is greatfully acknowledged.
Educ. Counsel., 2005, 59, 97.
17 (a) V. C. Jordan, Endocr.-Relat. Cancer, 2014, 21, R235; (b)
S. Husain, S. N. Alvi and R Nageswara Rao, Anal. Lett.,
1
994, 27, 2485.
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