4010
M. S. Kim, S. L. Diamond / Bioorg. Med. Chem. Lett. 16 (2006) 4007–4010
15. Compound 5: yield 63%. 1H NMR (CDCl3): 7.91–7.46 (m,
13H, –(C6H5), –2(NO2C6H4)), 5.55 (m, 4H, 2(–CH2–)).
13C NMR (CDCl3): 153.0, 134.0, 133.1, 131.9, 131.7,
128.8, 128.5, 124.9, 64.4. Anal. Calcd for C20H17N2PO7:
C, 56.08; H, 4.00, N; 6.54. Found: C; 55.92; H; 3.93, N;
6.16.
o-nitrobenzyl derivatives. This detail decomposition
study can serve as the basis for the design of new gene
delivery system (i.e., photolytic cationic polymers) to
control gene release using photoirradiation. Further
research on the synthesis of gene carrier modified with
o-nitrobenzyl derivatives for triggered extracellular or
intracellular DNA release by photoirradiation is now
in progress.
16. 1-o-Nitrophenylethyl alcohol: yield 95%. 1H NMR
(CDCl3): 7.83–7.32 (m, 4H, –(C6H4)), 5.30 (m, 1H,
(–CH–)), 3.16 (br, 1H, OH), 1.46 (d, J = 6.2 Hz, CH3).
17. Compound 6: yield 69%. 1H NMR (CDCl3): 7.91–7.20 (m,
7H, –(C6H4), –(C6H3)), 6.12 (m, 1H, (–CH–)), 2.40 (s, 3H,
CH3), 1.64 (d, J = 6.2 Hz, CH3). 13C NMR (CDCl3):
144.8, 133.8, 133.1, 129.7, 128.7, 128.1, 127.7, 124.2, 75.3,
23.5, 21.5. Anal. Calcd for C15H15NSO5: C; 56.06, H; 4.70,
N; 4.36. Found: C; 56.54; H; 4.65, N; 4.07.
References and notes
1. Fisher, R. S.; Ho, J. CNS Drugs 2002, 16, 579.
2. Epe, B.; Muller, E.; Adam, W.; Saha-Moller, C. R. Chem.
Biol. Interact. 1992, 85, 265.
18. Compound 7: yield 65%. 1H NMR (CDCl3): 7.88–7.34 (m,
4H, –(C6H4)), 5.91 (m, 1H, –CH–), 3.93 (m, 4H, 2CH2),
1.60 (d, J = 6.2 Hz, 3H, CH3), 1.15 (m, 6H, 2CH3). 13C
NMR (CDCl3): 169.4, 146.6, 137.6, 133.5, 128.4, 127.6,
124.1, 71.7, 63.7, 24.1, 15.6. Anal. Calcd for C12H18NPO6:
C; 47.53, H; 5.98, N; 4.62. Found: C; 47.20, H; 6.37, N;
4.58.
3. Givens, R. S.; Kueper, L. W., III Chem. Rev. 1993, 93, 55.
4. Olejnik, J.; Sonar, S.; Krzymanska-Olejnik, E.; Roths-
child, K. J. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 7590.
5. Ramamurthy, V.; Schanze, K. S. Organic Molecular
Photochemistry; Marcel Dekker, Inc: New York, 1999.
6. Holmes, C. P.; Jones, D. G. J. Org. Chem. 1995, 60, 2318.
7. Holmes, C. P. J. Org. Chem. 1997, 62, 2370.
8. Smet, M.; Liao, L. X.; Dehaen, W.; McGrath, D. Org.
Lett. 2000, 2, 511.
19. Compound 8: yield 72%. 1H NMR (CDCl3): 8.08–7.25 (m,
9H, –(C6H4), –(C6H5)), 6.57 (m, 1H, (–CH–)), 1.79 (d,
J = 6.2 Hz, CH3). 13C NMR (CDCl3): 165.3, 147.6, 138.0,
133.6, 133.1, 129.5, 128.3, 127.0, 124.4, 68.7, 22.0. Anal.
Calcd for C15H13NO4: C; 66.41, H; 4.83, N; 5.16. Found:
C; 66.76, H; 5.02, N; 4.86.
20. Jean, S.; Bideau, C.; Bellon, L.; Halimi, G.; De Meo, M.;
Orsiere, T.; Dumenil, G.; Berge-Lefranc, J. L.; Botta, A.
Biochim. Biophys. Acta 2001, 1522, 89.
9. McCray, J. A.; Trentham, D. R. Annu. Rev. Biophys.
Biophys. Chem. 1989, 18, 239.
10. Kim, M. S.; Gruneich, J.; Diamond, S. L., in preparation.;
11. Compound 1: yield 51%. 1H NMR (CDCl3): 8.12–7.36 (m,
8H, –2(C6H4)), 5.48 (s, 2H, (–CH2–)), 2.46 (s, 3H, CH3).
Anal. Calcd for C14H13NSO5: C, 54.71; H, 4.26, N; 4.56.
Found: C; 54.68; H; 4.05, N; 4.11.
21. Setlow, R. B.; Grist, E.; Thompson, K.; Woodhead, A. D.
Proc. Natl. Acad. Sci. U.S.A. 1993, 87, 6666.
12. Compound 2: yield 51%. 1H NMR (CDCl3): 7.95–7.43 (m,
8H, –(C6H4), –(C6H4)), 2.50 (s, 3H, CH3). Anal. Calcd for
C15H11NSO5: C; 56.78, H; 3.49, N; 4.41. Found: C; 56.40;
H; 3.28, N; 4.22.
22. Photolysis was performed at a distance of 10 cm using
Rayonet Photochemical Chamber Reactor Model RPR-
100 (Southern New England Ultraviolet Company [0.6–
0.8 mW/cm2]) which was equipped with 12 UV lamps
(each 21 W) used for 300 nm and ENF-240 C (SPEC-
TRONICS Corp., Optical density is 0.3 mW/cm2 at
15 cm), Model XX-15 L (UVP Inc, Optical density is
1.6 mW/cm2 at 15 cm), and Model B-100A Hi Intensity
UV Lamp (UVP Inc, Optical density is 3.5 mW/cm2 at
30 cm) for 365 nm.
13. Compound 3: yield 75%. 1H NMR (CDCl3): 8.65–7.42 (m,
10H, –(C6H4), –(C12H6)), 2.51 (s, 3H, CH3). Anal. Calcd
for C19H13NSO5: C; 62.12, H; 3.57, N; 3.81. Found: C;
61.99; H; 3.30, N; 3.59.
14. Compound 4: yield 31%. 1H NMR (CDCl3): 8.18–7.48 (m,
4H, –C6H4), 5.51 (d, J = 6.9 Hz, 2H, (–CH2–)), 4.18 (m,
4H, 2CH2), 1.35 (m, 6H, 2CH3). Anal. Calcd for
C11H16NPO6: C, 45.68; H, 5.58, N; 4.84. Found: C;
45.50; H; 5.64, N; 4.29.
23. Walker, J. W.; McCray, J. A.; Hess, G. P. Biochemistry
1986, 25, 1799.