2692
W.-H. Chen et al. / Bioorg. Med. Chem. Lett. 15 (2005) 2689–2692
Baldeyron, B.; Colson, P.; Rasoanaivo, P.; Mambu, L.;
349.1309. Found: 349.1318. Compound 3d: 1H NMR
(DMSO-d6, 300 MHz) d 1.65–1.80 (m, 2H, CH2CH2CH2O),
1.99 (m, 4H, CH2CH2CH2O), 3.15–3.23 (m, 4H, 5-H), 4.04
(s, 6H, OCH3), 4.32 (t, 4H, J = 6.3 Hz, OCH2CH2), 4.93
(t, 4H, J = 6.4 Hz, 6-H), 6.16 (s, 4H, OCH2O), 7.07 (s, 2H,
4-H), 7.75 (s, 2H, 1-H), 7.97 (d, 2H, J = 8.7 Hz, 12-H), 8.18
(d, 2H, J = 8.7 Hz, 11-H), 8.90 (s, 2H, 13-H), 9.75 (s, 2H,
8-H); HRMS for C43H40N2O8 ([Mꢀ2Cl]2+) calcd: 356.1387.
Found: 356.1385. Compound 3e: 1H NMR (DMSO-d6,
300 MHz) d 1.60 (s, 4H, CH2CH2CH2O), 1.90–2.00 (m, 4H,
CH2CH2CH2O), 3.15–3.23 (m, 4H, 5-H), 4.03 (s, 6H,
OCH3), 4.29 (t, 4H,J = 5.8 Hz, OCH2CH2), 4.92 (t, 4H,
J = 6.9 Hz, 6-H), 6.16 (s, 4H, OCH2O), 7.07 (s, 2H, 4-H),
7.75 (s, 2H, 1-H), 7.97 (d, 2H, J = 9.3 Hz, 12-H), 8.18 (d,
2H, J = 9.3 Hz, 11-H), 8.90 (s, 2H, 13-H), 9.73 (s, 2H, 8-H);
HRMS for C44H42N2O8 ([Mꢀ2Cl]2+) calcd: 363.1471.
Found: 363.1504.
Frappier, F.; Bailly, C. Eur. J. Pharm. Sci. 2003, 20, 381–
391; (i) Park, H.; Kim, E. H.; Sung, Y.-H.; Kang, M. R.;
Chung, I. K.; Cheong, C.; Lee, W. Bull. Korean Chem. Soc.
2004, 25, 539–544; (j) Chen, W.-H.; Chan, C.-L.; Cai, Z.;
Luo, G.-A.; Jiang, Z.-H. Bioorg. Med. Chem. Lett. 2004,
14, 4955–4959; (k) Chen, W.-H.; Qin, Y.; Cai, Z.; Chan, C.-
L.; Luo, G.-A.; Jiang, Z.-H. Bioorg. Med. Chem. 2005, 13,
1859–1866.
5. Iwasa, K.; Kamigauchi, M.; Ueki, M.; Taniguchi, M. Eur.
J. Med. Chem. 1996, 31, 469–478.
6. Structural data for compound 3a: 1H NMR (DMSO-d6,
300 MHz) d 3.17 (s, 4H, 5-H), 4.02 (s, 6H, OCH3), 4.79 (s,
4H, OCH2), 4.85 (s, 4H, 6-H), 6.16 (s, 4H, OCH2O), 7.08 (s,
2H, 4-H), 7.75 (s, 2H, 1-H), 7.98 (d, 2H, J = 9.6 Hz, 12-H),
8.19 (d, 2H, J = 9.6 Hz, 11-H), 8.91 (s, 2H, 13-H), 9.83 (s,
2H, 8-H); HRMS for C40H34N2O8 ([Mꢀ2Cl]2+) calcd:
335.1152. Found: 335.1129. Compound 3b: 1H NMR
(CD3OD–CDCl3, 300 MHz,) d 2.65 (m, 2H, CH2CH2O),
3.23 (t, 4H, J = 6.3 Hz, 5-H), 4.09 (s, 6H, OCH3), 4.76 (t,
4H, OCH2CH2), 4.92 (t, 4H, 6-H), 6.09 (s, 4H, OCH2O),
6.91 (s, 2H, 4-H), 7.59 (s, 2H, 1-H), 7.98 (d, 2H, J = 9.0 Hz,
12-H), 8.07 (d, 2H, J = 9.0 Hz, 11-H), 8.65 (s, 2H, 13-H),
7. Association constants are derived from nonlinear
curve fitting, using the equation I = I0 + ((I1 ꢀ I0)/
2[B]0) {([DNA]0 + [B]0 + 1/Ka) ꢀ (([DNA]0 + [B]0 + 1/Ka)2 ꢀ
4[DNA]0[B]0)1/2}, wherein [DNA]0 and [B]0 are the initial
concentrations of DNA and 3a–e, respectively. I, I0, and I
1
represent the fluorescence intensities of the sample, 3a–e
alone and the intensity when 3a–e are totally bound,
respectively. For reference, see: (a) Schneider, H.-J.; Yat-
simirski, A. K. In Principles and Methods in Supramolecular
Chemistry; J Wiley: New York, 2000, pp 137–143; (b) Xi,
Z.; Jones, G. B.; Qabaja, G.; Wright, J.; Johnson, F.;
Goldberg, I. H. Org. Lett. 1999, 1, 1375–1377.
9.87 (s, 2H, 8-H); HRMS for C41H36N2O8 ([Mꢀ2Cl]2+
)
calcd: 342.1231. Found: 342.1213. Compound 3c: 1H NMR
(DMSO-d6, 300 MHz) d 2.14 (s, 4H, CH2CH2O), 3.15–3.24
(m, 4H, 5-H), 4.04 (s, 6H, OCH3), 4.40 (t, 4H, J = 5.6 Hz,
OCH2CH2), 4.93 (s, 4H, 6-H), 6.17 (s, 4H, OCH2O), 7.08 (s,
2H, 4-H), 7.78 (s, 2H, 1-H), 7.98 (d, 2H, J = 9.0 Hz, 12-H),
8.19 (d, 2H, J = 9.0 Hz, 11-H), 8.92 (s, 2H, 13-H), 9.78 (s,
2H, 8-H); HRMS for C42H38N2O8 ([Mꢀ2Cl]2+) calcd:
8. Leng, F.; Priebe, W.; Chaires, J. B. Biochemistry 1998, 37,
1743–1752.