125.3, 125.6, 127.3, 129.2, 129.7, 132.4, 133.7, 140.6, 143.1, 146.1,
180.7, 181.8. FT-IR (KBr): 3269, 2332, 1518, 1323, 1267, 1166,
1065, 1021, 831, 767, 729, 669 cm−1. UV (DMSO): 521 nm (e =
21 344), 596 nm (e = 10 253), 643 nm (e = 10 626). HRMS (FAB)
calcd for C37H30F3N7O4S2 [M+] 757.1744; found 757.1756.
Acknowledgements
We thank the National Science Council of the Republic of China
for financial support (NSC 95-2113-M-126-002) and the National
Center for High-Performance Computation.
1-(4-Nitronaphthylthiourelyene-ethene-amino)-4-(4-
nitrophenylthiourelyene-ethene-amino)anthraquinone (2)
References
1 J. L. Pierre and P. Baret, Bull. Soc. Chim. Fr., 1983, 367.
2 M. Mei and S. Wu, New J. Chem., 2001, 25, 471.
A similar procedure to the synthesis of 1 was carried out using
3 (a) C. Suksai and T. Tuntulani, Chem. Soc. Rev., 2003, 32, 192;
(b) R. Martinez-Manez and F. Sancenon, Chem. Rev., 2003, 103, 4419;
(c) X. H. Qian and F. Liu, Tetrahedron Lett., 2003, 44, 795; (d) J. L.
Sessler, S. Camiolo and P. A. Gale, Coord. Chem. Rev., 2003, 240, 17;
(e) P. D. Beer and E. J. Hayes, Coord. Chem. Rev., 2003, 240, 167; (f) P. A.
Gale, Chem. Rev., 2003, 240, 191; (g) D.-W. Yoon, H. Hwang and C.-H.
Lee, Angew. Chem., Int. Ed., 2002, 41, 1757; (h) J. Ren, Q. Wang, D.
Qu, X. Zhao and H. Tian, Chem. Lett., 2004, 33, 974; (i) B. Liu and H.
Tian, Chem. Lett., 2005, 34, 686; (j) V. Amendola, D. Esteban-Go´mez,
L. Fabbrizzi and M. Licchelli, Acc. Chem. Res., 2006, 39, 343.
4 (a) P. A. Gale, Coord. Chem. Rev., 2001, 213, 79; (b) P. D. Beer and P. A.
Gale, Angew. Chem., Int. Ed., 2001, 40, 486.
5 (a) T. R. Kelly and M. H. Kim, J. Am. Chem. Soc., 1994, 116, 7072;
(b) E. Fan, S. A. Van Arman, S. Kincaid and A. D. Hamilton, J. Am.
Chem. Soc., 1993, 115, 369; (c) K. S. Jeong, J. W. Park and Y. L. Cho,
Tetrahedron Lett., 1996, 37, 2795; (d) P. Schiessl and F. P. Schmidtchen,
Tetrahedron Lett., 1993, 34, 2449; (e) P. D. Beer, M. G. B. Drew,
C. Hazlewood, D. Hesek, J. Hodacova and S. E. Stokes, J. Chem.
Soc., Chem. Commun., 1993, 229; (f) M. S. Goodman, V. Jubian and
A. D. Hamilton, Tetrahedron Lett., 1995, 36, 2551; (g) J. L. Sessler,
A. Andrievsky, V. Kral and L. Vincent, J. Am. Chem. Soc., 1997, 119,
9385; (h) C. Bazzicalupi, A. Bencini, A. Bianchi, V. Fusi, E. Garcia-
Espana, C. Giorgi, J. M. Llinares, J. A. Ramirez and B. Valtancoli,
Inorg. Chem., 1999, 38, 620; (i) J.-L. Wu, Y.-B. He, Z.-Y. Zeng, L.-H.
Wei, L.-Z. Meng and T.-X. Yang, Tetrahedron, 2004, 60, 4309; (j) T.
Gunnlaugsson, A. P. Davis, J. E. O’Brient and M. Glynn, Org. Lett.,
2002, 4, 2449; (k) J. J. Lavigne and E. V. Anslyn, Angew. Chem., Int. Ed.,
1999, 38, 3666; (l) A. Metzger and E. V. Anslyn, Angew. Chem., Int.
Ed., 1998, 37, 649; (m) S.-Y. Liu, Y.-B. He, W. H. Chan and A. W. M.
Lee, Tetrahedron, 2006, 62, 11687.
4-nitrophenylisothiocyanate in place of 4-trifluoromethylphenyl-
◦
1
isothiocyanate. Yield: 0.16 g (41%), mp: 197–199 C. H NMR
(400 MHz, DMSO-d6): d 3.74–3.76 (m, 8H), 7.69–7.71 (m, 2H),
7.75–7.82 (m, 7H), 8.09–8.15 (m, 4H), 8.25–8.31 (m, 3H), 8.54
(br s, 2H), 10.28 (br s, 2H), 10.91 (br s, 2H). 13C NMR (DMSO-
d6): d 40.6, 40.8, 44.0, 108.9, 109.0, 114.7, 120.9, 122.4, 123.9,
124.7, 125.9, 127.6, 129.9, 132.6, 134.0, 142.1, 143.4, 146.2, 180.8,
181.0, 181.1, 182.2. FT-IR (KBr): 3263, 3053, 2935, 2858, 2341,
1639, 1593, 1568, 1506, 1322, 1250 cm−1. UV (DMSO): 360 nm
(e = 24 925), 596 nm (e = 15 195), 643 nm (e = 17 544). HRMS
(FAB) calcd for C36H30N8O6S2 [M+] 734.1730; found 734.1719.
1-(4-Nitronaphthylthiourelyene-ethene-amino)-4-(4-
cyanophenylthiourelyene-ethene-amino)anthraquinone(3)
A
similar procedure to the synthesis of 1 was carried
out using 4-cyanophenylisothiocyanate in place of 4-trifluoro-
methylphenylisothiocyanate. Yield: 0.15 g (36%), mp: 197–198 ◦C.
1H NMR (400 MHz, DMSO-d6): d 3.73–3.76 (m, 8H), 7.66–7.68
(m, 2H), 7.75–7.82 (m, 6H), 8.11 (d, 2H, J = 8.4 Hz), 8.26–8.30
(m, 6H), 8.42 (d, 2H, J = 8.8 Hz), 10.14 (br s, 2H), 10.91 (br s,
2H). 13C NMR (DMSO-d6): d 39.6, 39.8, 44.0, 108.8, 122.5, 122.8,
123.8, 124.7, 125.5, 125.8, 127.6, 129.4, 130.1, 132.8, 134.1, 141.1,
143.5, 146.3, 181.2, 182.1. FT-IR (KBr): 3295, 3064, 2928, 2854,
2335, 1570, 1510, 1310, 1264, 1170 cm−1. UV (DMSO): 524 nm
(e = 10 320), 596 nm (e = 11 160), 643 nm (e = 13 540). HRMS
(FAB) calcd for C37H30N8O4S2 [M+] 714.8153; found 714.8157.
6 (a) Y.-P. Yen and K.-W. Ho, Tetrahedron Lett., 2006, 47, 1193; (b) Y.-P.
Yen and K.-W. Ho, Tetrahedron Lett., 2006, 47, 7357.
7 (a) F. Sancenon, R. Martinez-Manez, M. A. Miranda, M.-J. Segui and
J. Soto, Angew. Chem., Int. Ed., 2003, 42, 647; (b) A. M. Costero, M.
Colera, P. Gavina and S. Gil, Chem. Commun., 2006, 761.
8 (a) J. Tepinski, D. Pawlowska and S. Angielski, Acta Biochim. Pol., 1984,
31, 229; (b) A. Gougoux, G. Lemieux and N. Lavoie, Am. J. Physiol.,
1976, 231, 1010; (c) S. EiamOng, M. Spohn, N. A. Kurtzman and S.
Sabatini, Kidney Int., 1995, 48, 1542.
1-(4-Nitronaphthylthiourelyene-ethene-amino)-4-(phenyl-
thiourelyene-ethene-amino)anthraquinone (4)
A similar procedure to the synthesis of 1 was carried out
9 G. Latini, Clin. Chim. Acta, 2005, 361, 20.
using phthylisothiocyanate in place of 4-trifluoromethylphenyl-
10 C. W. Greenhalgh and N. Hughes, J. Chem. Soc. C, 1968, 85, 1284.
11 K. A. Connors, Binding Constants. The Measurement of Molecular
Complex Stability, John Wiley and Sons, New York, 1987.
12 S. Gronert, J. Am. Chem. Soc., 1993, 115, 10258.
13 (a) L. J. Altman, D. Laungani, G. Gunnarsson, H. Wennerstrom and S.
Forsen, J. Am. Chem. Soc., 1978, 100, 8264; (b) P. Schah-Mohammedi,
I. G. Shenderovich, C. Detering, H.-H. Limbach, P. M. Tolstoy, S. N.
Smirnov, G. S. Denisov and N. S. Golubev, J. Am. Chem. Soc., 2000,
122, 12878.
14 M. Boiocchi, L. Del Boca, D. Esteban-Gomez, L. Fabbrizzi, M.
Licchelli and E. Monzani, J. Am. Chem. Soc., 2004, 126, 16507.
15 Y.-J. Kim, S. J. Kwak, J. S. Lee, H. J. Kwon Nam, S. H. K. Lee and C.
Kim, Tetrahedron, 2006, 62, 9635.
16 P. J. Choi, K. A. Petterson and J. D. Roberts, J. Phys. Org. Chem., 2002,
15, 278.
◦
1
isothiocyanate. Yield: 0.23 g (59%), mp: 206–207 C. H NMR
(400 MHz, DMSO-d6): d 3.72–3.75 (m, 8H), 7.60–7.64 (m, 1H),
7.67–7.73 (m, 2H), 7.76–7.86 (m, 6H), 8.10 (d, 2H, J = 8.4 Hz),
8.26–8.34 (m, 6H), 8.41 (d, 2H, J = 8.4 Hz), 10.13 (br s, 2H),
10.92 (br s, 2H). 13C NMR (DMSO-d6): d 30.9, 40.8, 44.3, 108.9,
122.4, 122.9, 123.9, 124.8, 125.6, 125.9, 127.7, 129.5, 130.0, 132.7,
134.0, 141.0, 143.4, 146.4, 181.1, 182.2. FT-IR (KBr): 3293, 3068,
2930, 2853, 2330, 1639, 1568, 1506, 1311, 1265, 1168, 1045, 1025,
830 cm−1. UV (DMSO): 382 nm (e = 10 438), 523 nm (e = 8768),
596 nm (e = 17 290), 643 nm (e = 19 294). HRMS (FAB) calcd for
C36H31N7O4S2 [M+] 689.1789; found 689.1792.
3598 | Org. Biomol. Chem., 2007, 5, 3592–3598
This journal is
The Royal Society of Chemistry 2007
©