Design, synthesis, and pharmacological investigation of iodined salicylimines, new prototypes of antimicrobial drug candidates

Article abstract of DOI:10.1002/ardp.200900129

A series of 3,5-diiodo-salicylalidene Schiff bases (compounds 1 - 35) has been synthesized and tested for antimicrobial activity. The compounds were assayed for antibacterial activities by the MTT method. Some of the compounds inhibit the growth of a broad range of bacteria including the species of Bacillus subtilis, Staphylococcus aureus, Streptococcus faecalis, Pseudomonas aeruginosa, Escherichia coli, and Enterobacter cloacae. Among them, compounds 2-[(4-chloro-phenylimino)-methyl]-4,6-diiodo-phenol 11 and 2,4-diiodo-6-[(2- morpholin-4-yl-ethylimino)methyl]phenol 19 showed the most potent antibacterial activity with MIC of 3.1, 12.9, 3.3, 6.5, 12.9, 3.3 and 3.2, 12.8, 3.2, 12.8, 12.8, 3.2 μM against B. subtilis, S. aureus, S. faecalis, P. aeruginosa, E. Coli, and E. cloacae, respectively.

Full text of DOI:10.1002/ardp.200900129

282
Arch. Pharm. Chem. Life Sci. 2010, 343, 282–290
Full Paper
Design, Synthesis, and Pharmacological Investigation of
Iodined Salicylimines, New Prototypes of Antimicrobial Drug
Candidates
Suo-Ping Xu1,2, Peng-Cheng Lv1,2, Lei Shi1,2, and Hai-Liang Zhu1,2
1 Key Laboratory of Anhai Educational Department, Anhai University of Technology, Maanshan, P.R. China
2 School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, P.R. China
A series of 3,5-diiodo-salicylalidene Schiff bases (compounds 1–35) has been synthesized and
tested for antimicrobial activity. The compounds were assayed for antibacterial activities by the
MTT method. Some of the compounds inhibit the growth of a broad range of bacteria including
the species of Bacillus subtilis, Staphylococcus aureus, Streptococcus faecalis, Pseudomonas aeruginosa,
Escherichia coli, and Enterobacter cloacae. Among them, compounds 2-[(4-chloro-phenylimino)-
methyl]-4,6-diiodo-phenol 11 and 2,4-diiodo-6-[(2-morpholin-4-yl-ethylimino)methyl]phenol 19
showed the most potent antibacterial activity with MIC of 3.1, 12.9, 3.3, 6.5, 12.9, 3.3 and 3.2,
12.8, 3.2, 12.8, 12.8, 3.2 lM against B. subtilis, S. aureus, S. faecalis, P. aeruginosa, E. Coli, and E.
cloacae, respectively.
Keywords: Antibacterial activity / 3,5-Diiodosalicylalidene / Schiff base / Structure-activity relationship /
Received: June 9, 2009; Accepted: December 11, 2009
DOI 10.1002/ardp.200900129
tron-withdrawing substituents on that ring were calcu-
Introduction
lated to increase the electropositive surface area on the
halogen [11]. In addition, C. L. Gentry et al. reported that
halogen insertion can increase membrane partitioning
and permeability and, therefore, improve the oral
absorption or enhance the blood-brain barrier permeabil-
ity [12, 13]. From these former investigations we con-
cluded that compounds of 3,5-diiodosalicylaldehyde
could possess potential biological activities and antimi-
crobial properties. In this paper, the synthesis of some
compounds of 3,5-diiodo-salicylaldehyde with primary
amines are reported and the results of this study may be
useful for researchers attempting to gain more under-
standing of the antimicrobial activity of 3,5-diiodosalicyl-
alidene Schiff base' compounds.
Compounds with the structure of AC=NB are known as
Schiff bases, which are usually synthesized from the con-
densation of primary amines and active carbonyl groups.
Salicylaldehyde-type Schiff bases show a wide spectrum
of antimicrobial properties [1–5]. Lots of researchers stud-
ied the synthesis, characterization, and structure-activity
relationship (SAR) of Schiff bases [6–9]. It is also reported
that salicylaldehyde derivatives, with one or more halo-
atoms in the aromatic ring, showed a variety of biological
activities like anti-bacterial and antifungal activities [10].
Furthermore, chlorine, bromine, and especially iodine in
small organic molecules have an anisotropic surface-
charge distributions, including significant electroposi-
tive patches which make it possible for these halogens to
serve as Lewis acids for certain geometries. For example,
if the halogen is located on an aromatic ring, then elec-
Chemistry
In the present study, a series of simple Schiff bases have
been designed and synthesized with 3,5-diiodosalicylali-
dene and 35 different primary amines (Scheme 1). Four
compounds (5, 6, 8, and 9) were determined by X-ray dif-
fraction analysis for their molecular structures. The
Correspondence: Hai-Liang Zhu, State Key Laboratory of Pharmaceuti-
cal Biotechnology, Nanjing University, Nanjing Jiangsu 210093, P.R.
China.
E-mail: zhuhl@nju.edu.cn and xsp62@xznu.edu.cn
Fax: +86-25-8359 2672
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Arch. Pharm. Chem. Life Sci. 2010, 343, 282–290
Iodined Salicylimines
283
Scheme 1. Syntheses of the Schiff bases.
molecular structures of compounds 5, 6, 8, and 9 are
showed in Fig. 1; their crystallographic data are presented
in Table 1, and their selected bond lengths are given in
Table 2. All the compounds gave satisfactory chemical
analyses (€ 0.4%). H-NMR, IR spectroscopy, and ESI-MS
spectra were consistent with the assigned structures.
Pharmacology
All the synthesized compounds were screened for anti-
bacterial activity against three Gram-(+) bacterial strains
(Bacillus subtilis, Staphylococcus aureus, and Streptococcus
faecalis) and three Gram-(–) bacterial strains (Escherichia
1
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S.-P. Xu et al.
Arch. Pharm. Chem. Life Sci. 2010, 343, 282–290
Table 1. Crystal structure data for compounds 5, 6, 8, and 9.
Compound
5
6
8
9
Formula
C13H8FI2NO
467.02
0.260.160.1
Monoclinic
Cc
C10H11I2NO
415.00
0.260.160.1
Orthorhombic
pbca
C13H8ClI2NO
483.45
0.260.160.1
Orthorhombic
Pnma
C13H8BrI2NO
527.92
0.360.260.1
Triclinic
P–1
Mr
Crystal size (mm3)
Crystal system
Space group
a (ꢀ)
b (ꢀ)
c (ꢀ)
a (8C)
4.5485 (13)
35.025 (10)
17.307 (5)
90
95.255 (4)
90
2745.6 (14)
8
2.260
10.7019 (14)
7.1483 (9)
32.404 (4)
90
90
90
2478.9 (5)
8
2.502
15.8432 (17)
6.9942 (8)
13.1975 (14)
90
90
90
1462.4 (3)
4
2.196
7.9870 (13)
8.9811 (14)
11.3907 (18)
91.093 (2)
99.873 (2)
114.570 (2)
728.4 (2)
b (8C)
c (8C)
V (ꢀ3)
Z
2
Dc (g/cm–1)
2.413
7.045
l (mm–1)
4.578
5.676
4.471
F (000)
1728
1728
896
486
h range (8C)
1.66/27.43
–5/5,–44/44,–22/20
6250
2.28/27.52
–13/13,–9/8,–41/42
19683
2.01/27.61
–20/20,–9/9,–17/17
9861
1.82/27.62
–10/10,–10/11,–14/14
6439
Index range (h,k,l)
Measured reflections
Observed reflections I > 2 s (I)
Min. and max. Transmission
Data/restraints/parameters
Goodness-of-fit on F2
R1, w R2[I > 2 s (I)]
R1, w R2
3136
2849
1829
3315
0.3500/0.5560
3136/2/327
1.021
0.0685/0.1622
0.0937/0.1790
0.4684/0.6634
1829/1/113
0.976
0.0387/0.1385
0.0423/0.1436
1.128/–0.757
0.198/0.494
3315/0/164
0.874
0.0328/0.0961
0.0480/0.1117
1.328/–0.807
2849/0/129
1.222
0.0355/0.1000
0.0465/0.1074
1.020/–0.909
Large diff. peak and hole(e ꢀ–3) 2.042/–1.240
Table 2. Important bond lengths (in ꢀ) of compounds 5, 6, 8, and
9.
coli, Pseudomonas aeruginosa, and Enterobacter cloacae) by
the MTT method. The MICs (minimum inhibitory concen-
trations) of the complexes against six bacteria are pre-
sented in Table 3. Also included are the activity data of
reference compounds penicillin (North China Pharma-
ceutical Co. Ltd, D0211107, Hebei, China) and kanamycin
(Nanjing Zhuyan Biotechnology Co. Ltd, Amresco
060D0504, Nanjing, China).
5
6
8
9
C7-N1
C2-O1
C3-I1
1.23(2)
1.33(2)
2.040(17) 2.091(5)
2.104(18) 2.097(5)
1.48(2)
1.30(2)
1.280(7)
1.326(7)
1.278(10) 1.276(6)
1.325(9)
2.100(6)
2.090(6)
1.425(8)
–
1.341(6)
2.091(5)
2.101(5)
1.427(6)
–
C5-I2
C8-N1
C11-F1
C9-Cl1
C11-Br1
1.472(7)
–
–
–
–
–
1.709(7)
–
–
1.905(5)
Results and discussion
Schiff base compounds with different structures react
with bacteria differently in activity. Structural analysis
of these compounds may provide some explanation for
the structure-activity relationships. Such an analysis
might be helpful in the design of better inhibitors. The
biological activity of a particular substance depends on a
complex sum of individual properties including com-
pound structure, affinity for the target site, and survival
in the medium of application, survival within the biolog-
ical system, transport properties, and the state of the tar-
get organism [14]. In this study, we focused our attention
on the structure-activity relationships.
values of 3.1, 12.9, 3.3, 6.5, 12.9, 3.3 and 3.2, 12.8, 3.2,
12.8, 12.8, 3.2 lM against B. subtilis, S. aureus, S. faecalis, P.
aeruginosa, E. coli and E. cloacae, respectively.
As shown in Table 3, it can be concluded that com-
pounds with aromatic rings were more active than com-
pounds with aliphatic chains. For example, in general,
compounds 4, 5, 8–17 showed higher antibacterial activ-
ity than many other compounds. Among the compounds
with aromatic rings, compound 4, 5, 8–11 and 13–17
showed the highest activity. This observation indicated
that the aromatic ring structure with tert-electron with-
drawing group (F, Cl, Br, I) had a higher antibacterial
activity.
Among the compounds tested, compounds 11 and 19
showed the most potent antibacterial activity with MIC
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Arch. Pharm. Chem. Life Sci. 2010, 343, 282–290
Iodined Salicylimines
285
Table 3. MICs (minimum inhibitory concentrations in lM) of the synthetic compounds.
Compound
MICs (lM)
Gram-positive
Gram-negative
B. subtilis
S. aureus
S. faecalis
P. aeruginosa
E. coli
E. cloacae
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
29.2
3.6
3.3
26.1
6.7
15.2
7.5
12.9
5.9
10.9
3.1
13.4
13.3
48.3
3.1
5.1
48.3
3.3
3.2
6.2
6.7
50.9
3.4
13.3
12.2
22.8
3.2
30.3
14.8
14.6
14.9
28.3
1.9
29.1
58.2
26.9
13.1
26.8
60.2
55.8
12.9
11.9
21.7
12.9
6.8
26.8
24.2
12.9
20.5
12.4
27.0
12.8
3.2
53.6
25.5
53.8
3.4
48.7
2.9
25.8
2.0
15.0
7.4
14.5
58.2
3.4
6.6
13.4
7.5
14.0
25.8
23.8
21.7
3.3
26.8
107.1
48.3
25.8
10.3
3.1
3.3
3.2
6.3
3.4
6.4
6.7
6.8
48.7
22.8
3.3
7.8
3.9
3.7
15.0
7.1
3.9
8.0
116.5
58.2
107.9
26.4
26.8
60.2
7.0
25.8
5.9
5.4
29.1
58.2
107.9
3.3
3.3
30.1
7.0
3.2
23.8
2.7
12.9
13.4
53.6
6.0
14.8
1.562
53.9
13.1
3.3
15.0
14.0
12.9
2.8
10.8
3.3
26.8
3.3
6.5
13.4
107.1
96.6
25.8
41.3
96.8
108.0
12.8
25.0
53.6
101.9
53.8
53.3
6.1
22.8
6.5
15.2
3.9
3.7
1.8
6.0
3.3
10.3
12.1
3.3
6.5
2.5
24.2
54.0
12.8
12.5
6.7
6.4
6.7
3.4
12.2
22.8
12.9
3.9
30.0
14.8
30.0
3.6
3.2
12.5
53.6
51.0
53.8
13.3
6.1
22.8
12.9
7.8
7.5
7.4
30.0
3.6
30.8
8.0
15.0
7.1
15.4
4.0
8.0
3.6
14.2
7.8
16.0
4.0
18.7
6.4
33
34
35
7.8
7.9
4.0
3.6
0.8
16.0
32.0
18.7
6.4
16.0
3.6
6.4
16.0
9.3
3.2
Penicillin
Kanamycin
4.6
Conclusion
Experimental
A series of 3,5-diiodo-salicylalidene Schiff bases have General
The 3,5-diiodosalicylalidene was synthesized with salicylalde-
hyde, KI, and KIO3 [5]. The other chemicals (reagent grade) used
were commercially available. All the 1H-NMR spectra were
recorded on a Bruker DPX 300 model spectrometer (Bruker Bio-
science, USA) in CDCl3 or DMSO-d6. Chemical shifts (d) for1H-NMR
spectra were reported in parts per million to residual solvent
protons. IR spectra were recorded on a Nexus 870 FT-IR (Thermo
Nicolet, Madison, WI, USA). ESI-MS spectra were recorded on a
Mariner System 5304 Mass spectrometer. Elemental analyses
were performed on a CHN-O-Rapid instrument (Heraeus, Ger-
many) and were within €0.4% of the theoretical values. Melting
points were measured on a Boetius micro melting-point appara-
tus.
been synthesized and tested for their antimicrobial activ-
ity by the MTT method. Biological data indicated that
most compounds showed potent antibacterial activity
against the six bacterial strains. Most importantly, com-
pounds 11 and 19 showed the most potent antibacterial
activity with MIC values of 3.1, 12.9, 3.3, 6.5, 12.9, 3.3 and
3.2, 12.8, 3.2, 12.8, 12.8, 3.2 lM against B. subtilis, S. au-
reus, S. faecalis, P. aeruginosa, E. coli and E. cloacae, respec-
tively.
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ethanol, washed with ethanol for three times, and dried in a
vacuum desiccator containing anhydrous CaCl2.
2-Butyliminomethyl-4,6-diiodophenol 1
Yellow crystals, yield: 90%, m.p.: 84–868C, standing for 3 d;
selected IR data (cm–1, KBr): 2953.5 (s), 1645.1 (s), 1214.6 (s), 544.2
(m);1H-NMR (300 MHz, CDCl3) d ppm: 15.074 (s, 1H), 8.052 (s, 1H),
8.038 (d, J = 2.1 Hz, 1H), 7.466 (d, J = 2.1 Hz, 1H), 3.619 (d, J = 12.9
Hz, 2H), 1.692 (d, J = 14.7 Hz, 2H), 1.427 (d, J = 30.0 Hz, 2H), 0.949
(d, J = 14.7 Hz, 3H); ESI-MS C11H14I2NO+: 429.9 [M+ + H]. Anal. calcd.
for C11H13I2NO: C, 30.79; H, 3.05; N, 3.26. Found: C, 30.89; H, 3.12;
N, 3.34.
2-(tert-Butyliminomethyl)-4,6-diiodophenol 2
Yellow crystals, yield: 92%, m.p.: 115–1178C, standing for 3 d;
selected IR data (cm–1, KBr): 2967.7 (s), 1631.8 (s), 1214.9 (s), 539.8
(m); 1H-NMR (300 MHz, CDCl3) d ppm: 15.714 (s, 1H), 8.043 (d, J =
2.1 Hz, 1H), 8.014 (s, 1H), 7.469 (d, J = 2.1 Hz, 1H), 1.404 (s, 9H);
ESI-MS C11H14I2NO+: 429.9 [M+ + H]. Anal. calcd. for C11H13I2NO: C,
30.79; H, 3.05; N, 3.26. Found: C, 30.88; H, 3.17; N, 3.13.
2-(Benzyliminomethyl)-4,6-diiodophenol 3
Brown dope, yield: 87%, standing for 3 d; selected IR data (cm–1,
1
KBr): 1625.0 (s), 1277.5 (m), 1158.0 (s), 598.7 (m); H-NMR (300
MHz, CDCl3) d ppm: 15.714 (s, 1H), 8.220 (s, 1H), 8.075 (d, J = 2.1
Hz, 1H), 7.551 (d, J = 2.1 Hz, 1H), 7.390 (d, J = 7.5 Hz, 2H), 7.352 (d,
J = 6.3 Hz, 2H), 7.310 (d, J = 12.3 Hz, 1H), 4.851 (s, 2H); ESI-MS
C14H12I2NO+: 463.9 [M+ + H]. Anal. calcd. for C14H11I2NO: C, 36.31;
H, 2.39; N, 3.02. Found: C, 36.16; H, 2.52; N, 3.17.
2-(4-Fluorobenzyliminomethyl)-4,6-diiodophenol 4
Yellow crystals, yield: 85%, m.p.: 107–1088C, standing for 3 d;
selected IR data (cm–1, KBr): 1624.3 (s), 1271.4 (m), 1158.2 (s),
566.7 (m); 1H-NMR (300 MHz, CDCl3) d ppm: 14.674 (s, 1H), 8.194
(s, 1H), 8.050 (d, J = 2.1 Hz, 1H), 7.525 (d, J = 2.1 Hz, 1H), 7.247 (d,
J = 8.7 Hz, 2H), 7.064 (d, J = 8.7 Hz, 2H), 4.874 (s, 2H); ESI-MS
C14H11FI2NO+: 481.9 [M+ + H]. Anal. calcd. for C14H10FI2NO: C,
34.96; H, 2.10; N, 2.91. Found: C, 35.08; H, 2.19; N, 3.08.
2-[(4-Fluorophenylimino)methyl]-4,6-diiodophenol 5
Nacarat crystals, yield: 90%, m.p.: 145–1478C, standing for 4 d;
selected IR data (cm–1, KBr): 1614.6 (s), 1280.0 (m), 1150.0 (s),
532.9 (m); 1H-NMR (300 MHz, CDCl3) d ppm: 14.467 (s, 1H), 8.426
(s, 1H), 8.113 (d, J = 2.1 Hz, 1H), 7.764 (d, J = 2.1 Hz, 1H), 7.274 (d,
J = 8.1 Hz, 2H), 7.152 (d, J = 8.1 Hz, 2H); ESI-MS C13H9FI2NO+: 467.9
[M+ + H]. Anal. calcd. for C13H8FI2NO: C, 33.43; H, 1.73; N, 3.00.
Found: C, 34.58; H, 1.62; N, 2.89.
Displacement ellipsoids are draw at the 30% probability level.
Figure 1. Molecular structures of 5, 6, 8, and 9.
(E)-2,4-diiodo-6-((propylimino)methyl)phenol 6
Kelly crystals, yield: 81%, m.p.: 72–738C, standing for 4 d;
selected IR data (cm–1, KBr): 2957.2 (s), 1631.1 (s), 1276.2 (s), 548.8
(m);1H-NMR (300 MHz, CDCl3) d ppm: 15.065 (s, 1H), 8.057 (s, 1H),
8.041 (d, J = 2.1 Hz, 1H), 7.471 (d, J = 2.1 Hz, 1H), 3.586 (d, J = 13.5
Hz, 2H), 1.753 (d, J = 28.8 Hz, 2H), 0.990 (d, J = 13.5 Hz, 3H); ESI-MS
C10H12I2NO+: 415.9 [M+ + H]. Anal. calcd. for C10H11I2NO: C, 28.94;
H, 2.67; N, 3.38. Found: C, 28.78; H, 2.48; N, 3.24.
General method for the synthesis of compounds 1–27
Equimolar quantities (0.4 mmol) of 3,5-diiodo-salicylaldehyde
and the primary amine with one amino group were dissolved in
ethanol (10 mL) and stirred at room temperature for 10–15 min
to give a clear solution. After standing for approximately 3–5 d,
the precipitates were separated by filtration, recrystallized from
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Arch. Pharm. Chem. Life Sci. 2010, 343, 282–290
Iodined Salicylimines
287
Hz, 1H), 7.356 (d, J = 12.6 Hz, 1H); ESI-MS C13H9FI2NO+: 467.9 [M+ +
H]. Anal. calcd. for C13H8FI2NO: C, 33.43; H, 1.73; N, 3.00. Found:
C, 33.36; H, 1.66; N, 2.93.
2,4-Diiodo-6-phenyliminomethylphenol 7
Saffron crystals, yield: 91%, m.p.: 145–1478C, standing for 4 d;
selected IR data (cm–1, KBr): 1611.2 (s), 1279.4 (m), 1149.9 (s),
534.8 (m); 1H-NMR (300 MHz, CDCl3) d ppm: 14.688 (s, 1H), 8.456
(s, 1H), 8.107 (d, J = 2.1 Hz, 1H), 7.671 (d, J = 2.1 Hz, 1H), 7.433 (d,
J = 7.8 Hz, 2H), 7.303 (d, J = 1.8 Hz, 1H), 7.267 (d, J = 7.8 Hz, 2H);
ESI-MS C13H10I2NO+: 449.9 [M+ + H]. Anal. calcd. for C13H9I2NO: C,
34.77; H, 2.02; N, 3.12. Found: C, 34.55; H, 1.92; N, 3.01.
2-[(2,4-Dichlorophenylimino)methyl]-4,6-diiodophenol 14
Bisque crystal, yield: 91%, m.p.: 173–1748C, standing for 5 d;
selected IR data (cm–1, KBr): 1606.6 (s), 1290.7 (m), 1150.9 (s),
544.3 (m); 1H-NMR (300 MHz, DMSO-d6) d ppm: 14.298 (s,1H),
8.980 (s, 1H), 8.198 (d, J = 2.1 Hz, 1H), 8.022 (d, J = 2.1 Hz, 1H),
7.814 (d, J = 2.4 Hz, 1H), 7.685 (d, J = 8.4 Hz, 1H), 7.596 (d, J = 8.4
Hz, 1H); ESI-MS C13H8Cl2I2NO+: 517.8 [M+ + H]. Anal. calcd. for
C13H7Cl2I2NO: C, 30.15; H, 1.36; N, 2.70. Found: C, 30.09; H, 1.32;
N, 2.65.
2-[(2-Chlorophenyliminomethyl)-4,6-diiodophenol 8
Nacarat crystal, yield: 90%, m.p.: 150–1528C, standing for 4 d;
selected IR data (cm–1, KBr): 1608.1 (s), 1272.6 (m), 1152.6 (s),
537.5 (m); 1H-NMR (300 MHz, CDCl3) d ppm: 14.231 (s, 1H), 8.460
(s, 1H), 8.134 (d, J = 2.1 Hz, 1H), 7.690 (d, J = 2.1 Hz, 1H), 7.505 (d,
J = 7.8 Hz, 1H), 7.573 (d, J = 19.8 Hz, 2H), 7.232 (d, J = 7.8 Hz, 1H);
ESI-MS C13H9ClI2NO+: 483.8 [M+ + H]. Anal. calcd. for C13H8ClI2NO:
C, 32.30; H, 1.67; N, 2.90. Found: C, 32.15; H, 1.56; N, 2.85.
2-[(2,4-Difluorophenylimino)methyl]-4,6-diiodophenol 15
Bisque crystal, yield: 86%, m.p.: 154–1558C, standing for 5 d;
selected IR data (cm–1, KBr): 1615.4 (s), 1266.4 (s), 1150.4 (s), 478.9
(m); 1H-NMR (300 MHz. DMSO-d6) d ppm: 14.383 (s, 1H), 8.982 (s,
1H), 8.175 (d, J = 2.1 Hz, 1H), 8.007 (d, J = 2.1 Hz, 1H), 7.715 (d, J =
6.0 Hz,1H), 7.455 (d, J = 11.1 Hz, 1H), 7.256 (d, J = 13.2 Hz, 1H); ESI-
MS C13H8F2I2NO+: 485.9 [M+ + H]. Anal. calcd. for C13H7F2I2NO: C,
32.19; H, 1.45; N, 2.89. Found: C, 32.06; H, 1.41; N, 2.92.
2-[(4-Bromophenyliminomethyl)-4,6-diiodophenol 9
Bisque crystal, yield: 90%, m.p.: 175–1788C, standing for 4 d;
selected IR data (cm–1, KBr): 1607.5 (s), 1276.0 (s), 1154.7 (s), 527.9
(s); 1H-NMR (300 MHz, CDCl3) d ppm: 14.325 (s, 1H), 8.433 (s, 1H),
8.118 (d, J = 2.1 Hz, 1H), 7.689 (d, J = 2.1 Hz, 1H), 7.565 (d, J = 9.0
Hz, 2H), 7.161 (d, J = 9.0 Hz, 2H); ESI-MS C13H9BrI2NO+: 527.8 [M+ +
H]. Anal. calcd. for C13H8BrI2NO: C, 29.58; H, 1.53; N, 2.65. Found:
C, 29.36; H, 1.43; N, 2.55.
2-[(2,4-Dibromophenylimino)methyl]-4,6-diiodophenol 16
Bisque crystal, yield: 93%, m.p.: 208–2108C, standing for 5 d;
selected IR data (cm–1, KBr): 1604.5 (s), 1288.6 (m), 1149.9 (s),
1
544.3 (m); H-NMR (300 MHz, DMSO-d6) d ppm: 14.152 (s, 1H),
8.941 (s, 1H), 8.200 (d, J = 2.4 Hz, 1H), 8.047 (d, J = 2.4 Hz, 1H),
8.027 (d, J = 2.1 Hz, 1H), 7.600 (d, J = 8.7 Hz, 1H), 7.596 (d, J = 8.7
Hz, 1H); ESI-MS C13H8Br2I2NO+: 605.7 [M+ + H]. Anal. calcd. for
C13H7Br2I2NO: C, 25.73; H, 1.16; N, 2.31. Found: C, 25.65; H, 1.14;
N, 2.28.
2,4-Diiodo-6-[(4-iodophenylimino)methyl]phenol 10
Brown crystal, yield: 85%, m.p.: 180–1838C, standing for 4 d;
selected IR data (cm–1, KBr): 1606.0 (s), 1275.7 (m), 1155.3 (s),
528.4 (m); 1H-NMR (300 MHz, CDCl3) d ppm: 14.352 (s, 1H), 8.431
(s, 1H), 8.117 (d, J = 2.1 Hz, 1H), 7.764 (d, J = 8.7 Hz, 2H), 7.671 (d,
J = 2.1 Hz, 1H), 7.031 (d, J = 8.7 Hz, 2H); ESI-MS C13H9I3NO+: 575.8
[M+ + H]. Anal. calcd. for C13H8I3NO: C, 27.16; H, 1.40; N, 2.44.
Found: C, 27.23; H, 1.32; N, 2.51.
2-[(3,5-Dichlorophenylimino)methyl]-4,6-diiodophenol 17
Nacarat crystal, yield: 92%, m.p.: 253–2558C, standing for 5 d;
selected IR data (cm–1, KBr): 1608.2 (s), 1277.2 (m), 1158.0 (s),
1
532.5 (m); H-NMR (300 MHz, DMSO-d6) d ppm: 13.775 (s, 1H),
2-[(4-Chlorophenyliminomethyl]-4,6-diiodophenol 11
Saffron crystal, yield: 82%, m.p.: 143–1458C, standing for 4 d;
selected IR data (cm–1, KBr): 1611.3 (s), 1279.8 (m), 1151.8 (s),
8.933 (s, 1H), 8.190 (d, J = 2.1 Hz, 1H), 7.991 (d, J = 2.1 Hz, 1H),
7.622 (d, J = 1.8 Hz, 2H), 7.580 (d, J = 1.8 Hz, 1H); ESI-MS
C13H8Cl2I2NO+: 517.8 [M+ + H]. Anal. calcd. for C13H7Cl2I2NO: C,
30.15; H, 1.36; N, 2.70. Found: C, 29.92; H, 1.31; N, 2.64.
1
531.4 (m); H-NMR (300 MHz, DMSO-d6) d ppm: 14.408 (s, 1H),
8.931 (s, 1H), 8.180 (d, J = 2.1 Hz, 1H), 8.018 (d, J = 2.1 Hz, 1H),
7.571 (d, J = 2.7 Hz, 2H), 7.556 (d, J = 2.7 Hz, 2H); ESI-MS
C13H9ClI2NO+: 483.8 [M+ + H]. Anal. calcd. for C13H8ClI2NO: C,
32.30; H, 1.67; N, 2.90. Found: C, 32.18; H, 1.62; N, 2.81.
2,4-Diiodo-6-(p-tolyliminomethyl)phenol 18
Nacarat crystal, yield: 87%, m.p.: 145–1468C, standing for 5 d;
selected IR data (cm–1, KBr): 2911.8 (m), 1616.3 (s), 1280.2 (m),
1154.2 (s), 534.1 (m); 1H-NMR (300 MHz, DMSO-d6) d ppm: 14.886
(s, 1H), 8.910 (s, 1H), 8.123 (d, J = 2.1 Hz, 1H), 7.971 (d, J = 2.1 Hz,
1H), 7.398 (d, J = 8.7 Hz, 2H), 7.299 (d, J = 8.7 Hz, 2H), 2.348 (s, 3H);
ESI-MS C14H12I2NO+: 463.9 [M+ + H]. Anal. calcd. for C14H11I2NO: C,
36.31; H, 2.39; N, 3.02. Found: C, 36.27; H, 2.36; N, 2.97.
2-[(4-Hydroxyphenylimino)methyl]-4,6-diiodophenol 12
Nacarat crystal, yield: 92%, m.p.: 227–2308C, standing for 4 d;
selected IR data (cm–1, KBr): 3046.2 (m), 1619.7 (s), 1277.2 (s),
1137.2 (m), 524.0 (m); 1H-NMR (300 MHz, DMSO-d6) d ppm: 15.120
(s, 1H), 9.814 (s, 1H), 8.862 (s, 1H), 8.105 (d, J = 2.1 Hz, 1H), 7.946
(d, J = 2.1 Hz, 1H), 7.410 (d, J = 1.8 Hz, 2H), 6.893 (d, J = 1.8 Hz, 2H);
ESI-MS C13H10I2NO+: 465.9 [M+ + H]. Anal. calcd. for C13H9I2NO: C,
33.58; H, 1.95; N, 3.01. Found: C, 33.43; H, 1.92; N, 2.94.
2,4-Diiodo-6-[(2-morpholin-4-yl-ethylimino)methyl]phenol
19
Yellow crystal, yield: 82%, m.p.: 86–888C, standing for 5 d;
selected IR data (cm–1, KBr): 3423.2 (m), 2816.7 (s), 1640.6 (s),
1278.6 (m), 1113.9 (s), 539.8 (m); 1H-NMR (300 MHz, CDCl3) d
ppm: 14.810 (s, 1H), 8.119 (d, J = 2.1 Hz, 1H), 8.050 (s, 1H), 7.496
(d, J = 2.1 Hz, 1H), 3.722 (s, 6H), 2.709 (s, 2H), 2.530 (s, 4H); ESI-MS
2-[(2-Fluorophenylimino)methyl]-4,6-diiodophenol 13
Nacarat crystal, yield: 95%, m.p.: 121–1228C, standing for 4 d;
selected IR data (cm–1, KBr): 1614.3 (s), 1279.1 (m), 1150.0 (s),
522.7 (m); H-NMR (300 MHz, DMSO-d6) d ppm: 14.579 (s, 1H),
9.006 (s, 1H), 8.175 (d, J = 2.1 Hz, 1H), 8.023 (d, J = 2.1 Hz, 1H),
7.643 (d, J = 15.6 Hz, 1H), 7.412 (d, J = 4.5 Hz, 1H), 7.369 (d, J = 4.5
1
+
C13H17I2N2O2 : 486.9 [M+ + H]. Anal. calcd. for C13H16I2N2O2: C,
32.12; H, 3.32; N, 5.76. Found: C, 32.06; H, 3.28; N, 5.81.
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288
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Arch. Pharm. Chem. Life Sci. 2010, 343, 282–290
2,4-Diiodo-6-[(3-morpholin-4-yl-
2-[(1-Benzylpiperidin-4-ylimino)methyl]-4,6-diiodophenol
prorylimino)methyl]phenol 20
26
Yellow dope, yield: 80%, standing for 5 d; selected IR data (cm–1,
KBr): 3445.6 (m), 2923.1 (s), 1629.4 (s), 1275.4 (m), 1114.7 (s),
545.6 (m); 1H-NMR (300 MHz, CDCl3) d ppm: 14.935 (s, 1H), 8.102
(d, J = 2.1 Hz, 1H), 8.045 (s, 1H), 7.474 (d, J = 2.1 Hz, 1H), 3.715 (d,
J = 12.6 Hz, 6H), 2.429 (d, J = 12.6 Hz, 6H), 1.898 (d, J = 27.3 Hz,
Yellow crystal, yield: 80%, m.p.: 68–728C, standing for 3 d;
selected IR data (cm–1, KBr): 2938.8 (s), 2804.5 (s), 2761.8 (s),
1624.6 (s), 1283.0 (m), 1154.3 (s), 549.2 (m); H-NMR (300 MHz,
1
CDCl3) d ppm: 14.674 (s, 1H), 8.125 (s, 1H), 8.041 (d, J = 2.1 Hz, 1H),
7.479 (d, J = 2.1 Hz, 1H), 7.326 (d, J = 8.1 Hz, 4H), 7.262 (s, 1H),
3.533 (d, J = 6.6 Hz, 2H), 2.857 (d, J = 12 Hz, 2H), 2.062 (d, J = 21 Hz,
2H), 1.839 (d, J = 21 Hz, 4H), 1.461 (d, J = 21 Hz, 2H); ESI-MS
C19H21I2N2O+: 547.0 [M+ + H]. Anal. calcd. for C19H20I2N2O: C, 41.78;
H, 3.69; N, 5.13. Found: C, 40.84; H, 3.71; N, 5.20.
+
2H); ESI-MS C14H19I2N2O2 : 501.0 [M+ + H]. Anal. calcd. for
C14H18I2N2O2: C, 33.62; H, 3.63; N, 5.60. Found: C, 33.56; H, 3.58;
N, 5.56.
2,4-Diiodo-6-(pyridine-2-yliminomethyl)phenol 21
Nacarat crystal, yield: 96%, m.p.: 203–2058C, standing for 5 d;
selected IR data (cm–1, KBr): 3055.0 (m), 2989.1 (m), 1606.5 (s),
1428.7 (s), 1291.0 (m), 1158.5 (s), 527.8 (m); H-NMR (300 MHz,
DMSO-d6) d ppm: 14.761 (s, 1H), 9.411 (s, 1H), 8.578 (d, J = 2.1 Hz,
1H), 8.185 (d, J = 2.1 Hz, 1H), 8.154 (d, J = 2.1 Hz, 1H), 7.972 (d, J =
7.5 Hz, 1H), 7.432 (d, J = 4.8 Hz, 1H), 7.048 (d, J = 4.8 Hz, 1H); ESI-
MS C13H13I2N2O+: 466.9 [M+ + H]. Anal. calcd. for C13H12I2N2O: C,
33.50; H, 2.60; N, 6.01. Found: C, 33.44; H, 2.56; N, 5.93.
2,4-Diiodo-6-[(2-piperazin-1-yl-ethylimino)methyl]phenol
1
27
Red brown dope, yield: 82%, standing for 3 d; selected IR data
(cm–1, KBr): 2946.5 (m), 2822.3 (m), 1625.5 (s), 1280.2 (m), 1144.9
(s), 543.5 (m); H-NMR (300 MHz, CDCl3) d ppm: 15.075 (s, 1H),
1
8.094 (s, 1H), 8.044 (d, J = 2.1 Hz, 1H), 7.483 (d, J = 2.1 Hz, 1H),
3.726 (d, J = 10.8 Hz, 2H), 2.905 (s, 6H), 2.672 (d, J = 10.8 Hz, 4H),
2.504 (s, 1H); ESI-MS C13H18I2N3O+: 486.0 [M+ + H]. Anal. calcd. for
C13H17I2N3O: C, 32.19; H, 3.53; N, 8.66. Found: C, 32.02; H, 3.47; N,
8.73.
2,4-Diiodo-6-(isopropyliminomethyl)phenol 22
Nacarat crystal, yield: 90%, m.p.: 75–788C, standing for 5 d;
selected IR data (cm–1, KBr): 3348.6 (m), 3010.3 (m), 1612.3 (s),
1276.1 (m), 1174.7 (s), 530.2 (m); ESI-MS: 1H-NMR (300 MHz,
CDCl3) d ppm: 14.893 (s, 1H), 8.458 (s,1H), 8.090 (d, J = 2.1 Hz, 1H),
7.662 (d, J = 2.1 Hz, 1H), 7.302 (d, J = 8.4 Hz, 2H), 7.253 (d, J = 8.4
Hz, 2H), 2.959 (d, J = 27.6 Hz, 1H), 1.294 (s, 3H), 1.270 (s, 3H); ESI-
MS C16H16I2NO+: 491.9 [M+ + H]. Anal. calcd. for C16H15I2NO: C,
39.13; H, 3.08; N, 2.85. Found: C, 39.24; H, 3.04; N, 2.91.
General method for the synthesis of compounds 28–35
They were prepared by a procedure similar to that described
above, with 3,5-diiodo-salicylaldehyde (0.8 mmol) and the pri-
mary amine (0.4 mmol), with two amino groups.
2,4-Diiodo-6-[(pyridin-3-yl-methylimino)methyl]phenol 23
Yellow dope, yield: 85%, standing for 5 d; selected IR data (cm–1,
KBr): 3440.1 (m), 1617.5 (s), 1480.2 (s), 1194.6 (m), 524.5 (m); H-
NMR (300 MHz, CDCl3) d ppm: 14.376 (s, 1H), 8.582 (s, 2H), 8.292
(s, 1H), 8.068 (d, J = 2.1 Hz, 1H), 7.650 (d, J = 7.8 Hz, 1H), 7.563 (d,
J = 2.1 Hz, 1H), 7.317 (d, J = 12.6 Hz, 1H), 4.847 (s, 2H); ESI-MS
C13H11I2N2O+: 465.9 [M+ + H]. Anal. calcd. for C13H10I2N2O: C, 33.65;
H, 2.17; N, 6.04. Found: C, 33.54; H, 2.12; N, 6.11.
6,69-(1E,19E)-(Cyclohexane-1,2-diylbis(azan-1-yl-1-
ylidene))bis(methan-1-yl-1-ylidene)bis(2,4-diiodophenol)
28
1
Brilliant yellow crystal, yield: 92%, m.p.: 124–1278C, standing
for 3 d; selected IR data (cm–1, KBr): 3055.1 (m), 2927.9 (m), 2854.0
(m), 1624.2 (s), 1274.9 (s), 1155.8 (s), 658.4 (s), 551.6 (m); 1H-NMR
(300 MHz, CDCl3) d ppm: 14.566 (s, 2H), 8.124 (d, J = 2.1 Hz, 1H),
8.040 (s, 2H), 8.004 (d, J = 2.1 Hz, 1H), 7.514 (d, J = 2.1 Hz, 1H),
7.423 (d, J = 2.1 Hz, 1H), 3.352 (d, J = 9.3 Hz, 2H), 1.920 (d, J = 10.2
Hz, 2H), 1.823 (d, J = 10.2 Hz, 2H), 1.671 (d, J = 10.2 Hz, 2H), 1.470
2-(Cyclohexylmethyliminomethyl)-4,6-diiodophenol 24
Yellow crystal, yield: 87%, m.p.: 62–658C, standing for 5 d;
selected IR data (cm–1, KBr): 3310.4 (m), 2920.3 (s), 2849.0 (s).
1635.6 (s), 1275.3 (m), 1141.9 (m), 544.6 (m); 1H-NMR (300 MHz,
CDCl3) d ppm: 11.751 (s, 1H), 9.712 (s, 1H), 8.260 (d, J = 2.1 Hz, 1H),
7.847 (d, J = 2.1 Hz, 1H), 3.494 (s, 2H), 1.756 (s, 2H), 1.550 (s, 8H),
1.252 (s, 2H); ESI-MS C14H18I2NO+: 469.9 [M+ + H]. Anal. calcd. for
C14H17I2NO: C, 35.85; H, 3.65; N, 2.99. Found: C, 35.76; H, 3.61; N,
3.12.
+
(d, J = 10.2 Hz, 2H); ESI-MS C20H19I4N2O2 : 825.8 [M+ + H]. Anal.
calcd. for C20H18I4N2O2: C, 29.08; H, 2.20; N, 3.39. Found: C, 30.03;
H, 2.17; N, 3.32.
6,69-(1E,19E)-(3,39-Azanediylbis(propane-3,1-
diyl)bis(azan-1-yl-1-ylidene))bis(methan-1-yl-1-
ylidene)bis(2,4-diiodophenol) 29
2,4-Diiodo-6-[(2,2,6,6-tetramethylpiperidin-4-
ylimino)methyl]phenol 25
Yellow crystal, yield: 90%, m.p.: 55–588C, standing for 3 d;
selected IR data (cm–1, KBr): 3420.7 (m), 3053.9 (m), 2940.5 (m),
2844.2 (m), 2796.5 (m), 1631.2 (s), 1276.9 (m), 1154.6 (s), 655.7 (s),
540.8 (m); 1H-NMR (300 MHz, CDCl3) d ppm: 14.890 (s, 2H), 8.079
(s, 2H), 8.031 (d, J = 2.1 Hz, 2H), 7.453 (d, J = 2.1 Hz, 2H), 3.680 (d,
J = 13.5 Hz, 4H), 2.470 (s, 4H), 2.237 (s, 1H), 1.887 (d, J = 13.5 Hz,
Yellow crystal, yield: 83%, m.p.: 80–838C, standing for 3 d;
selected IR data (cm–1, KBr): 3375.8 (m), 3055.0 (m), 2954.0 (m),
2924.4 (m), 1626.9 (s), 1277.3 (m), 1153.5 (m), 553.5 (m); 1H-NMR
(300 MHz, CDCl3) d ppm: 15.079 (s, 1H), 9.738 (s, 1H), 8.070 (d, J =
2.1 Hz, 1H), 7.520 (d, J = 2.1 Hz, 1H), 3.845 (d, J =7.8 Hz, 2H), 3.519
(s, 4H), 3.413 (s, 1H), 1.309 (s, 6H), 1.236 (s, 6H); ESI-MS
C16H23I2N2O+: 513.0 [M+ + H]. Anal. calcd. for C16H22I2N2O: C, 37.52;
H, 4.33; N, 5.47. Found: C, 37.44; H, 4.31; N, 5.52.
+
4H); ESI-MS C20H22I4N3O2 : 843.8 [M+ + H]. Anal. calcd. for
C20H21I4N3O2: C, 28.49; H, 2.51; N, 4.98. Found: C, 28.31; H, 2.45;
N, 5.02.
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Arch. Pharm. Chem. Life Sci. 2010, 343, 282–290
Iodined Salicylimines
289
H]. Anal. calcd. for C17H14I4N2O2: C, 25.98; H, 1.80; N, 3.56. Found:
C, 26.15; H, 1.62; N, 3.69.
6,69-(1E,19E)-(Cyclohexane-1,3-diylbis(methylene))-
bis(azan-1-yl-1-ylidene)bis(methan-1-yl-1-
ylidene)bis(2,4-diiodophenol) 30
6,69-(1E,19E)-(Propane-1,2-diylbis(azan-1-yl-1-ylidene))-
bis(methan-1-yl-1-ylidene)bis(2,4-diiodophenol) 35
Brilliant yellow crystal, yield: 86%, m.p.: 105–1088C, standing
for 3 d; selected IR data (cm–1, KBr): 3054.1 (m), 2916.6 (s), 2843.3
(m), 1630.0 (s), 1282.0 (m), 1156.2 (s), 657.2 (m), 549.2 (m); H-
1
Yellow crystal, yield: 92%, m.p.: 166–1688C, standing for 3 d;
selected IR data (cm–1, KBr): 3052.8 (m), 2964.2 (m), 2925.3 (m),
2880.8 (m), 1627.2 (s), 1279.9 (m), 1153.1 (s), 656.9 (m), 551.7 (m);
1H-NMR (300 MHz, DMSO-d6) d ppm: 14.634 (s, 1H), 14.550 (s, 1H),
8.500 (s, 1H), 8.445 (s, 1H), 8.041 (d, J = 2.1 Hz, 1H), 8.028 (d, J = 2.1
Hz, 1H), 7.743 (d, J = 2.1 Hz, 1H), 7.712 (d, J = 2.1 Hz, 1H), 3.936 (d,
J = 3.0 Hz, 2H), 3.887 (d, J = 6.9 Hz, 1H), 1.346 (d, J = 6.0 Hz, 3H);
NMR (300 MHz, CDCl3) d ppm: 15.001 (s, 2H), 8.065 (s, 2H), 8.049
(d, J = 2.1 Hz, 2H), 7.496 (d, J = 2.1 Hz, 2H), 3.559 (d, J = 6.9 Hz, 2H),
3.499 (d, J = 6.9 Hz, 2H), 1.832 (s, 4H), 1.548 (s, 4H), 1.482 (d, J =
21.3 Hz, 2H); ESI-MS C22H23I4N2O2 : 854.8 [M+ + H]. Anal. calcd. for
+
C22H22I4N2O2: C, 30.94; H, 2.60; N, 3.28; Found: C, 30.79; H, 2.41;
N, 3.22.
ESI-MS C17H15I4N2O2 : 786.7[M+ + H]. Anal. calcd. for C17H14I4N2O2:
+
C, 25.98; H, 1.80; N, 3.56. Found: C, 26.18; H, 1.68; N, 3.45.
2-((E)-2-(((E)-2-Hydroxy-3,5-diiodobenzylideneamino)-
methyl)benzylideneamino)-4,6-diiodophenol 31
Antibacterial activity
Nacarat crystal, yield: 80%, m.p.: 237–2408C, standing for 3 d;
selected IR data (cm–1, KBr): 3055.8 (m), 1625.6 (s), 1272.9 (m),
1154.2 (s), 658.6 (m), 544.6 (m); 1H-NMR (300 MHz, CDCl3) d ppm:
14.131 (s, 1H), 11.745 (s, 1H), 9.708 (s, 1H), 8.339 (s, 1H), 8.256 (d,
J = 2.1 Hz, 1H), 8.125 (d, J = 2.1 Hz, 1H), 7.842 (d, J = 2.1 Hz, 1H),
7.455 (d, J = 2.1 Hz, 1H), 4.945 (s, 2H), 1.560 (s, 4H); ESI-MS
The antibacterial activity of the synthesized compounds was
tested against B. subtilis, S. aureus, S. faecalis, P. aeruginosa, E. coli,
and E. cloacae using MH medium (Mueller-Hinton medium:
casein hydrolysate 17.5 g, soluble 1.5 g, beef extract 1000 mL).
The MICs of the test compounds were determined by a colori-
metric method using the dye MTT [15]. A stock solution of the
synthesized compound (50 lg/mL) in DMSO was prepared and
graded quantities of the test compounds were incorporated in
specified quantity of sterilized liquid medium (MH medium for
antibacterial activity). A specified quantity of the medium con-
taining the compound was poured into microtitration plates. A
suspension of the microorganism was prepared to contain
approximately 105 cfu/mL and applied to microtitration plates
with serially diluted compounds in DMSO to be tested and incu-
bated at 378C for 24 h for bacteria. After the MICs were visually
determined on each of the microtitration plates, 50 lL of PBS
(phosphate buffered saline 0.01 mol/L, pH = 7.4, Na2HPO4 N 12
H2O 2.9 g, KH2PO4 0.2 g, NaCl 8.0 g, KCl 0.2 g, distilled water 1000
mL) containing 2 mg/mL of MTT was added to each well. Incuba-
tion was continued at room temperature for 4–5 h. The content
of each well was removed, and 100 lL of isopropanol containing
5% 1 mol/L HCl was added to extract the dye. After 12 h of incu-
bation at room temperature, the optical density (OD) was meas-
ured with a microplate reader at 570 nm. The observed MICs are
presented in Table 3.
C21H15I4N2O2 : 834.7 [M+ + H]. Anal. calcd. for C21H14I4N2O2: C,
+
30.24; H, 1.69; N, 3.36. Found: C, 30.08; H, 1.79; N, 3.29.
2-((5-(((E)-2-Hydroxy-3,5-diiodobenzylideneamino)-
methyl)-1,3,3-trimethylcyclohexyl)methyleneamino)-
4,6-diiodophenol 32
Brilliant yellow crystal, yield: 85%, m.p.: 137–1408C, standing
for 3 d; selected IR data (cm–1, KBr): 3055.1 (m), 2949.5 (m), 2912.0
(m), 2841.8 (m), 1627.1 (s), 1277.2 (m), 1153.6 (s), 657.3 (m), 549.0
(m);1H-NMR (300 MHz, CDCl3) d ppm: 15.053 (s, 1H), 9.804 (s, 1H),
8.192 (s, 1H), 8.105 (s, 1H), 8.083 (d, J = 2.1 Hz, 1H), 8.062 (d, J = 2.1
Hz, 1H), 7.557 (d, J = 2.1 Hz, 1H), 7.521 (d, J = 2.1 Hz, 1H), 3.397 (d,
J = 11.7 Hz, 2H), 1.664 (s, 4H), 1.437 (d, J = 12.3 Hz, 2H), 1.363 (s,
+
1H), 1.238 (s, 3H), 1.143 (s, 3H), 1.031 (s, 3H); ESI-MS C24H27I4N2O2 :
882.8 [M+ + H]. Anal. calcd. for C24H26I4N2O2: C, 32.68; H, 2.97; N,
3.18. Found: C, 32.86; H, 2.83; N, 3.24.
6,69-(1E,19E)-(2,29-Azanediylbis(ethane-2,1-diyl)bis(azan-
1-yl-1-ylidene))bis(methan-1-ylidene)bis(2,4-
diiodophenol) 33
The work was cofinanced by grants (Project 30772627) from the
National Natural Science Foundation of P.R. China and (Project
08XLA06) from the Scholastic Natural Science Foundation of Xuzhou
Normal University.
Yellow crystal, yield: 93%, m.p.: 108–1128C, standing for 3 d;
selected IR data (cm–1, KBr): 3295.1 (m), 3052.8 (m), 2888.8 (m),
2829.8 (m), 1633.5 (s), 1276.4 (m), 1156.7 (s), 656.9 (s), 540.6 (m);
1H-NMR (300 MHz, CDCl3) d ppm: 14.620 (s, 2H), 8.072 (s, 2H),
7.996 (d, J = 2.1 Hz, 2H), 7.937 (d, J = 2.1 Hz, 2H), 3.720 (s, 4H),
The authors have declared no conflict of interest.
+
3.042 (s, 4H), 1.563 (s, 1H); ESI-MS C18H18I4N3O2 : 815.8 [M+ + H].
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