40
MARYAM RAHBARI et al.
Table 3. Thermodynamic and binding parameters of HSA H, 3.51; N, 13.29%. Found: C, 60.60; H, 3.48; N,
with (Va ) at 280 nm
–f
λ
ex
13.66%.
–1
R2
G
° (kJ M–1)
Ligand Ka (M )
n
Δ
REFERENCES
(
Va
)
2.50
2.90
2.34
2.45
3.16
3.16
×
×
×
×
×
×
105
105
105
106
105
0.94
0.98
1.03
1.07
1.14
0.94
0.9945
0.9984
0.9604
0.9942
0.9774
0.9651
–30.79
–31.16
–30.63
–36.45
–31.38
–37.08
1. Bhattacharya, A.A., Grüne, T., and Curry, S., J. Mol.
Biol., 2000, vol. 303, pp. 721–732.
. Varshney, A., Sen, P., Ahmed, E., Rehan, M., and Subꢀ
(Vb
)
(
Vc)
2
(Vd
)
)
)
barao, N., Chirality, 2010, vol. 22, pp. 77–87.
(
Ve
Vf
3. Gulam,
J.,
Zunszain,
P.A.,
Petipas,
I.,
106
Bhattacharaya, A.A., Otagiri, M., and Curry, S., J. Mol.
Biol., 2005, vol. 353, pp. 38–52.
(
4
. Zaidi, N., Ahmad, E., Rehan, M., Rabbani, G., Ajmal,
M. R., Zaidi, Y., et al., J. Phys. Chem. B, 2013, vol. 117,
pp. 2595–2604.
q,
= 9.6), 7.61 (1H, d,
.2), 8.05 (1H, d, = 7.6), 8.28 (1H, d,
1 H, s), 11.90 (NH, br s); C NMR (DMSOꢀd6):
J
= 7.2), 7.26 (1H, dt,
= 9.6), 7.70 (1H, dt,
= 8.0), 8.37
J
= 7.6, 7.2), 7.48 (1H, d,
J
7
(
J
J
= 8.0,
5
. Moreno, F., Cortijo, M., and GonzalezꢀJimenez, J.,
J. Photochem. Photobiol., 1999, vol. 70, pp. 695–700.
J
J
13
6
. Sato, T., Saito, Y., Chikuma, M., Saito, Y., and
Nagai, S., Biol. Pharm. Bull., 2008, vol. 31, no. 3,
pp. 336–339.
. Jones, L.J., Haugland, R.P., and Singer, V.L., Biotechꢀ
niques, 2003, vol. 34, pp. 850–854.
1
5.3, 45.1, 102.6, 105.9, 110.1, 112.3, 112.6, 120.2,
126.6, 132.5, 133.4, 135.4, 135.8, 153.8, 158.4, 181.3.
IR: 3415 (NH), 1660 (C=O). MS,
+
m/z: 263 (
M
Calcd. for C H N O (263.3): C, 72.99; H, 4.98; N,
).
7
16
13
3
1
5.96%. Found: C, 72.78; H, 4.95; N, 15.76%.
ꢀChloroꢀ3ꢀethylꢀ6,11ꢀdihydroꢀ3 ꢀimidazo[4,5ꢀ
acridinꢀ11ꢀone (IVb) was obtained as pale yellow powꢀ
der (EtOH + CH CN), yield 63%, mp >300 C (deꢀ
= 7.2),
= 9.5, 2.1), 7.52
= 9.4), 8.10 (1H, d,
= 9.5) 8.37 (1H, s), 12.22
NH, br s); C NMR (DMSOꢀd6): 15.1, 45.3, 102.4,
8
. Belmont, P., Bosson, J., Godet, T., and Tiano, M.,
AntiꢀCancer Agents Med. Chem., 2007, vol. 7, pp. 139–
8
H
a]
169.
°
J
9. Kamal, A., Srinivas, O., Ramulu, P., Ramesh, G., and
K u m a r, P. P. , Bioorg. Med. Chem. Lett., 2004, vol. 14,
pp. 4107–4111.
3
1
comp). H NMR (DMSOꢀd6): 1.44 (3H, t,
.40 (2H, q, = 7.2), 7.27 (1H, dd,
1H, d, = 9.4), 7.68 (1H, d,
= 2.1), 8.28 (1H, d,
4
(
J
(
J
J
10. Demeunynck, M., Expert Opin. Ther. Pat., 2004,
J
J
vol. 14, pp. 55–70.
J
1
1. Robertson, I.G.C., Palmer, B.D., Officer, M.,
Siegers, D.J., Paxton, J.W., and Shaw, G.J., Biochem.
Pharmacol., 1991, vol. 42, pp. 1879–1884.
13
1
05.4, 109.4, 112.1, 112.8, 120.7, 126.9, 132.5, 133.7,
135.7, 142.1, 154.9, 157.8, 180.5. IR: 3392(NH), 1633
+
1
2. Tabarrini, O., Cecchetti, V., Fravolini, A.,
Nocentini, G., Barzi, A., Sabatini, S., Miao, H., and
Sissi, C., J. Heterocycl. Chem., 1999, vol. 42, pp. 2136–
2144.
(
C=O). MS,
14
m/z: 285 (
M
+ 2). Calcd. for
C H BrN O (283.7): C, 63.50; H, 3.55; N, 14.81%.
17
3
Found: C, 63.70; H, 3.58; N, 14.66%.
1ꢀChloroꢀ3ꢀethylꢀ3 ꢀimidazo[4,5ꢀ
was obtained as yellow crystals (CH CN), yield 70%,
13. Denny, W.A., Curr. Med. Chem., 2002, vol. 9, pp. 1655–
1
H
a]acridine (Va)
1665.
3
1
14. Goodell, J.R., Madhok, A.A., Hiasab, H., and Ferguꢀ
son, D.M., Bioorg. Med. Chem., 2006, vol. 14,
pp. 5467–5480.
mp 196–198
= 7.2), 4.43 (2H, q,
.83 (1H, dt, = 9.0, 7.2), 7.95 (1H, d,
1H, s), 8.07 (1H, dd, = 7.2, 2.0), 8.68 (1H, dd,
°C. H NMR (CDCl ): 1.67 (3H, t,
3
J
7
(
J
= 7.2), 7.65–7.69 (2H, m),
= 9.6), 8.03
J
J
15. KukowskaꢀKaszuba, M. and Dzierzbicka, K., Curr.
Med. Chem., 2007, vol. 14, pp. 3079–3104.
J
J
=
13
9
1
1
.0, 2.0); C NMR (CDCl ): 15.1, 43.4, 116.3, 119.5,
3
26.2, 127.6, 127.9, 128.3, 129.3, 130.7, 131.5, 132.3,
42.7, 144.9, 145.4, 149.8. MS,
1
6. Winter, R.W., Kelly, J.X., Smilkstein, M.J., Dodean R.,
Hinrichs, D., and Riscoe, M.K., Exp. Parasitol., 2008,
vol. 118, pp. 487–497.
+
m/
z: 283 (
M
+ 2).
Calcd. for C H ClN (281.7): C, 68.21; H, 4.29; N,
16
12
3
17. Smith, J.A., West, R.M., and Allen, M., J. Fluoresc.
2004, vol. 14, pp. 151–171.
18. Bl zquez, M.T., Mu iz, F.M., Sèez, S., Simón, L.M.,
,
1
4.91%. Found: C, 67.95; H, 4.25; N, 14.76%.
,11ꢀDichloroꢀ3ꢀethylꢀ3 ꢀimidazo[4,5ꢀ ]acridine
Vb) was obtained as yellow crystals (CH CN), yield
8
H
a
á
ñ
Alonso, A., Raposo, C., Lithgow, A., Alcázar, V., and
Morán, J.R., Heterocycles, 2006, vol. 69, pp. 73–81.
(
6
3
1
5%, mp 210–212
= 7.2), 1.88–2.11 (2H, m), 4.30 (2H, t,
= 9.2, 2.0), 7.89 (1H, d, = 9.2), 8.05 (1H,
= 9.2), 8.17 (1H, s), 8.23 (1H, d, = 2.0), 8.56
= 9.2); C NMR (CDCl ): 15.3, 43.6, 116.5,
°C. H NMR (CDCl ): 1.01 (3H, t,
3
1
2
2
9. Sadeghian,
A.,
Pordel,
M.
Safdari,
H.,
J
J = 7.2), 7.61
Fahmidekar, M.A., and Sadeghian, H., Med. Chem.
Res., 2012, vol. 21, pp. 3897–3901.
0. Rahimizadeh, M., Pordel, M., Bakavoli, M., Bakhtiarꢀ
poor, Z., and Orafaie, A., Monatsh. Chem., 2009,
vol. 140, pp. 633–638.
(
1H, dd,
d,
1H, d,
19.2, 125.7, 127.3, 128.3, 128.7, 129.7, 131.5, 133.2,
35.8, 142.3, 144.6, 145.8, 148.7. MS, : 320
+ 4). Calcd. for C H Cl N (316.1): C, 60.78;
J
J
J
J
13
(
J
3
1
1
m/z
1. Sahraei, R., Pordel, M., Behmadi, H., and Razavi, B.,
+
(M
J. Lumin., 2013, vol. 136, pp. 334–338.
16
11
2
3
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY Vol. 42
No. 1
2016