0.09 mmol) in anhydrous dimethoxyethane (0.5 mL) was added
dropwise. The reaction was stirred overnight before icy brine
was added to quench the reaction. The reaction mixture was
partitioned between CH2Cl2 and basified brine (pH = 11). The
organic layer was dried over Na2SO4, followed by solvent removal
under vacuum. The residue was chromatographed on alumina
gel by using 10% EtOAc in CH2Cl2. The isolated product was
precipitated from a CH2Cl2 solution by addition of hexanes to
afford pure trans-2a (14.9 mg, 46%). 1H NMR (300 MHz, CDCl3):
d (ppm) 8.81 (d, J = 1.8 Hz, 1H), 8.55 (d, J = 4.8 Hz, 1H), 8.52
(s, 1H), 8.38 (d, J = 8.4 Hz, 1H), 8.31 (d, J = 8.4 Hz, 1H), 8.02
(dd, J = 1.8, 8.4 Hz, 1H), 7.71–7.63 (m, 7H), 7.50 (d, J = 7.8 Hz,
1H), 7.29–7.18 (m, 3H), 7.18–7.14 (m, 2H), 3.95 (s, 6H), 2.41 (s,
3H); 13C NMR (75 MHz, CDCl3): d (ppm) 159.8, 155.9, 154.6,
153.6, 145.0, 149.4, 148.8, 137.6, 137.2, 136.6, 134.2, 133.7, 132.4,
130.3, 129.0, 123.2, 122.2, 121.9, 120.9, 120.9, 120.8, 60.5, 60.5,
18.6; HRMS (ESI+): calcd. (C31H28N6 + Na+) 507.2273, found
507.2255.
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A very irregular crystal of 2b was mounted on a nylon loop with the
useofheavy oil. The sample was held at -120◦C for datacollection.
Full data were taken on a Bruker SMART APEX diffractometer
using a detector distance of 5 cm. The number of frames taken was
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refined anisotropically and the hydrogens were assigned as a riding
model. Owing to the small size of the best crystal that could be
found, reflections were not found at as high an angle as we would
have liked.‡
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Acknowledgements
This work was supported, in part, by a New Investigator Research
grant from the James and Esther King Biomedical Research
Program administered by the Florida Department of Health
(08KN-16), National Science Foundation (CHE-0809201), and
National Institute of General Medical Sciences (R01GM-081382).
The authors also thank Chris Murphy at NHMFL for assistance
in live cell fluorescence imaging experiments.
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Notes and references
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40 See a preliminary study on a new heteroditopic design: R. J. Wandell, A.
H. Younes and L. Zhu, New J. Chem., 2010, DOI: 10.1039/c0nj00241k.
¯
‡ Crystallographic data of 2b: C36H31N5S2, MW = 597.78, Triclinic, P1 (Z◦=
˚
˚
˚
2), a = 6.2947(10) A, b = 9.8820(12) A, c = 25.1671(19) A, a = 86.318(5) ,
◦
◦
3
˚
b = 83.519(6) , g = 81.658(7) , V = 1537.2(3) A , T = 153 K, 2148 unique
reflections, Observed data with I > 2s(I) = 2091, R1 = 0.0378, wR2
=
0.0996.
This journal is
The Royal Society of Chemistry 2010
Org. Biomol. Chem., 2010, 8, 5431–5441 | 5441
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