Efficient green synthesis of isoindigo derivatives using sulfonic-acid-functionalized nanoporous silica (SBA-Pr-SO3H) catalyst and study of their antimicrobial properties

Article abstract of DOI:10.1007/s11164-012-0909-y

An efficient green condensation reaction has been developed for synthesis of trans-isoindigo derivatives using SBA-Pr-SO₃H with pore size of 6 nm as a heterogeneous nanoporous acid catalyst under solvent-free conditions. Isoindigo derivatives have many industrial applications, e.g., dyes, drugs, organic solar cells, and semiconductor memories. The antimicrobial activities of these compounds have also been tested.

Full text of DOI:10.1007/s11164-012-0909-y

Res Chem Intermed
DOI 10.1007/s11164-012-0909-y
Efficient green synthesis of isoindigo derivatives using
sulfonic-acid-functionalized nanoporous silica
(SBA-Pr-SO3H) catalyst and study of their
antimicrobial properties
•
Parisa Gholamzadeh Ghodsi Mohammadi Ziarani
•
•
Alireza Badiei Ali Abolhassani Soorki
Negar Lashgari
•
Received: 9 October 2012 / Accepted: 3 November 2012
Ó Springer Science+Business Media Dordrecht 2012
Abstract An efficient green condensation reaction has been developed for syn-
thesis of trans-isoindigo derivatives using SBA-Pr-SO3H with pore size of 6 nm as
a heterogeneous nanoporous acid catalyst under solvent-free conditions. Isoindigo
derivatives have many industrial applications, e.g., dyes, drugs, organic solar cells,
and semiconductor memories. The antimicrobial activities of these compounds have
also been tested.
Keywords SBA-Pr-SO3H ꢀ Isoindigo ꢀ Oxindole ꢀ Solvent-free reaction ꢀ
Green synthesis
Introduction
Indirubin is one of the active ingredients of a traditional Chinese recipe (Danggui
Longhui Wan) which has significant antitumor activity [1]. Poor solubility of this
compound in water has led to use of regioisomers with greater solubility. The blue
dye indigo is one of the oldest pigments, being used since ancient times. Currently,
indigo is widely used for textile dying [2, 3]. Isoindigo, indirubin, and indigo are
regioisomers that have recently attracted great attention not only as dyes but also in
various industries. In the pharmaceutical industry, meisoindigo is used for treatment
P. Gholamzadeh ꢀ G. Mohammadi Ziarani (&)
Department of Chemistry, Alzahra University, Vanak Square, Tehran, Iran
e-mail: gmziarani@hotmail.com
A. Badiei ꢀ N. Lashgari
School of Chemistry, College of Science, University of Tehran, Tehran, Iran
A. Abolhassani Soorki
Research Institute of Petroleum, Academic Center of Education, Culture & Research,
Shahid Beheshti University, Tehran, Iran
123

P. Gholamzadeh et al.
C
H
13
6
S
CH
3
CH
3
S
CH
H
N
3
C
H
17
8
8
C
H
17
H
N
O
N
CH
3
O
N
O
O
O
O
N
O
N
OACH
N
3
O
H
C
O
3
CH
3
N
OACH
S
3
n
OACH
3
H
C
3
H
C
S
3
NaturaTM
Meisoindigo
C
H
13
6
H
C
3
DAD
PFID
Fig. 1 Chemical structure of some isoindigo derivatives
of chronic myelogenous leukemia in China, and NaturaTM inhibits several cyclin-
dependent kinases (CDKs) [4]. CDK inhibitors can be used for treatment of
numerous diseases including cancer, diabetes, Alzheimer’s disease, stroke, cardio-
vascular disorder, Parkinson’s disease, inflammation, glomerulonephritis, and
acquired immunodeficiency syndrome [5]. Isoindigo compounds are starting
materials for the synthesis of future organic solar cells such as DAD type,1 and
PFID,2 which can be used in organic semiconductor memories (Fig. 1) [6–9].
Santa Barbara Amorphous (SBA-15) mesoporous silica was synthesized for the
first time in 1998 by Zhao et al. [10, 11]. This material has attracted great interest
because of its potential applications as a catalyst support [12]. SBA-15 is a
nanoporous silica with hexagonal structure, good accessibility due to high surface
area, large pore size, excellent (chemical and thermal) stability, high selectivity, and
easy isolation from products [13, 14]. Sulfonic-acid-functionalized nanoporous
silica (SBA-propyl-SO3H) as a green and heterogeneous nanoreactor with
noncorrosive properties was prepared by functionalization of SBA-15 [15, 16].
Experimental
The chemicals employed in this work were obtained from Merck Company and
were used with no purification. Infrared (IR) spectra were recorded from KBr disks
using a Fourier-transform (FT)-IR Bruker Tensor 27 instrument. Melting points
were measured by using the capillary tube method with an Electrothermal 9200
1
apparatus. H nuclear magnetic resonance (NMR, 250 and 500 MHz) was run on a
Bruker DPX using tetramethylsilane (TMS) as internal standard. Mass spectrometry
(MS) analysis was performed on a model 5973 mass-selective detector (Agilent).
Scanning electron microscopy (SEM) analysis was performed on a Philips XL-30
field-emission SEM operated at 16 kV, while transmission electron microscopy
(TEM) was carried out on a Tecnai G2 F30 at 300 kV. Ultraviolet–visible (UV–Vis)
spectra were run on a PerkinElmer Lambda 35 double-beam spectrophotometer.
1
DAD = donor–acceptor–donor.
PFID = poly{(9,9-dioctylfluorene)-2,7-diyl-alt-[N,N0-(2-ethylhexyl)-isoindigo]-60,6-diyl}.
2
123

Efficient green synthesis of isoindigo derivatives
Synthesis and functionalization of SBA-15
The nanoporous compound SBA-15 was synthesized and functionalized according
to our previous report [17], and the modified SBA-15-Pr-SO3H was used as a
nanoporous solid acid catalyst in the following reaction.
General procedure for preparation of isoindigo derivatives
SBA-Pr-SO3H was activated in vacuum at 100 °C, then, after cooling to room
temperature, oxindole (0.133 g, 1 mmol) and isatin derivatives (1 mmol) were
added to it. The mixture was heated in an oil bath (140 °C) for appropriate time as
shown in Table 1. After completion of the reaction, as monitored by thin-layer
chromatography (TLC), the crude product was dissolved in hot ethyl acetate and
then filtered to remove the solid catalyst. Filtrate was cooled to give the pure
product. The solid acid catalyst was subsequently washed with dilute acid solution,
distilled water, and acetone, and dried under vacuum. It can be used for several
times without significant loss of activity.
General procedure for preparation of N-substituted isatins
A mixture of isatin (10 mmol, 1.47 g) or 5-bromoisatin (10 mmol, 2.45 g),
potassium carbonate (13 mmol, 1.82 g), and the corresponding alkyl halide
(11 mmol) was dissolved in 10 ml dimethylformamide (DMF) and heated in an
oil bath at 120 °C under reflux condition. When the reaction was completed (as
monitored by TLC), the crude product was poured into iced water. If the product
crystallized, the resulting solid was filtered and washed well with water and purified
by recrystallization in EtOH. If not, the oily product was dissolved in ethyl acetate
and the organic layer washed with water and then dried to give pure product.
Table 1 SBA-Pr-SO3H-catalyzed synthesis of isoindigo derivatives 3
Entry
Numbers
R1
R2
R3
Time (h)
Yield (%)
Mp (°C)
Mp (lit.)
1
3a
3b
3c
3d
3e
3f
H
H
H
1
85
[300
364 [18]
380 [19]
New
2
H
H
Cl
Br
H
1/5
1/5
1
80
[300
3
H
H
60
[300
4
H
Me
CH2Ph
H
76
219–221
242–244
[300
223 [20]
238–241 [1]
[260 [21]
New
5
H
H
0.5
2
62
6
H
NO2
Br
H
70
7
3g
3h
3i
H
CH2Ph
Allyl
H
3
69
281–283
209–212
241–243
241–242
–
8
H
3
90
New
9
CH2Ph
CH2Ph
CH2Ph
CH2Ph
H
5
50
238–241 [1]
New
10
11
12
3j
CH2Ph
H
H
6
40
3k
3l
Br
Cl
6
Trace
Trace
–
H
6
–
–
123

P. Gholamzadeh et al.
General procedure for preparation of N-benzyloxindole
A solution of N-benzylisatin (5 mmol, 1.18 g) in hydrazine hydrate (6 ml) was
heated under reflux conditions for 1.5 h after completion of the reaction, the mixture
was diluted with water, then the product was dissolved in ethyl acetate (39 20 ml).
The combined organic phases were dried over MgSO4 and filtered, and the solvent
was evaporated in vacuo; the product recrystallized from diethyl ether to give pure
N-benzyloxindole.
5-Bromo-3,30-biindolinylidene-2,20-dione (3c)
IR (KBr): t = 3,271, 1,725, 1,684, 167, 470, 1,336, 1,166, 817, 747, and 662 cm-1
.
1H NMR (250 MHz, CDCl3): d = 6.82–8 (m, 9H) ppm. MS (m/e): 339 ([M ? 2]?,
95 %), 341 (M?, 90 %).
1-Benzyl-5-bromo-3,30-biindolinylidene-2,20-dione (3g)
IR (KBr): t = 3,205, 3,139, 3,084, 2,925, 1,696, 1,608, 1,465, 1,425, 1,333, 1,172,
1
808, and 772 cm-1. H NMR (500 MHz, CDCl3): d = 4.92 (s, 2H), 6.5. (d, 1H,
J = 8.4 Hz), 6.75 (d, 1H, J = 7.39 Hz), 7.2–7.35 (m, 6H), 7.4 (bs, 1H), 9.1 (d, 1H,
J = 8.4 Hz), 9.3 (s, 1H) ppm. MS (m/e): 432 (M ? 2, 85 %), 430 (M?, 80 %), 377
(20 %), 375 (18 %), 306 (40 %), 260 (20 %), 91 (100 %), 65 (16 %).
1-Allyl-3,30-biindolinylidene-2,20-dione (3h)
IR (KBr): t = 3,330, 3,249, 3,194, 3,064, 2,886, 1,727, 1,690, 1,617, 1,467, 1,333,
1,236, 110, and 775 cm-1 1H NMR (250 MHz, CDCl3): d = 4.4 (d, 1H,
.
J = 10.5 Hz), 5.30 (m, 2H), 5.85 (m, 1H), 6–7.7 (m, 7H), 8 (bs, 1H), 9.15 (d,
1H, J = 8.5 Hz) ppm. MS (m/e): 302 (M?, 20 %), 248 (60 %), 187 (80 %), 130
(100 %), 119 (65 %), 104 (63 %), 92 (43 %).
1,10-Dibenzyl-3,30-biindolinylidene-2,20-dione (3j)
IR (KBr): t = 3,100, 3,060, 2,950, 2,850, 1,689, 1,607, 1,466, 1,352, and 747 cm-1
.
1H NMR (250 MHz, CDCl3): d = 5 (s, 1H), 6.7 (d, 1H, J = 7.75 Hz), 7.0–7.23 (m,
7H), 9.2 (d, 1H, J = 7.75 Hz) ppm. MS (m/e): 442 (M?, 80 %), 414 (100 %), 351
(3 %), 323 (25 %), 295 (10 %), 91 (100 %), 65 (30 %).
Results and discussion
Chemistry
In this work, condensation of oxindole 1 with isatin derivatives 2 in the presence of
SBA-Pr-SO3H was studied (Scheme 1). As shown by the results in Table 2, among
the tested solvents and the solvent-free system, in H2O and EtOH, 3-hydroxy-3,
123

Efficient green synthesis of isoindigo derivatives
R1
N
O
R3
O
SBA-Pr-SO3H
+
O
O
R3
Solvent free,
140 °C
N
R1
N
R2
O
N
R2
2a-h
2 = H, Benzyl, Allyl, Me
R3 = H, Cl, Br, NO2
1a,b
R
R1 = H, Benzyl
3a-l
Scheme 1 General synthesis of isoindigo derivatives
Table 2 Optimization of reaction conditions for synthesis of isoindigo 3a
Entry
Solvent
Time (h)
Yield (%)
Color
Structure
1
2
H2O
0.5
4
95
92
White
White
H
N
O
EtOH
OH
O
N
H
Compound 4
3
4
5
DMF
DMSO
–
4
6
1
80
85
85
Red
Red
Red
H
N
O
O
N
H
Compound 3a
30-biindoline-2,20-dione (4) was obtained because in these solvents compound 4
cannot lose a H2O molecule to give isoindigo, whereas use of other solvents such as
DMF and dimethyl sulfoxide (DMSO), and solvent-free condition, resulted in
isoindigo products. The best result was achieved in the solvent-free system, with the
shortest reaction time in high yield. The high yields of this reaction are attributed to
the effect of the nanopore size of about 6 nm of SBA-Pr-SO3H, which could act as a
nanoreactor (Fig. 2). Therefore, this reaction was performed with different isatin
derivatives and oxindole and/or N-benzyloxindole between 0.5 and 6 h; the results
are summarized in Table 1. When the reaction was completed, the crude product
dissolved in hot ethyl acetate, and the catalyst was separated by filtration and
reactivated by simple washing subsequently with dilute acid solution, water, and
acetone for reuse without noticeable loss of reactivity. The new products were
characterized by IR and NMR spectroscopy data. Melting points are compared with
values reported in the literature in Table 1.
The suggested mechanism for the SBA-Pr-SO3H-catalyzed condensation is
shown in Scheme 2. Concerning the reaction mechanism, we suggest that, initially,
the solid acid catalyst protonates the carbonyl group of isatin 2. Enol form of
123

P. Gholamzadeh et al.
Fig. 2 SBA-Pr-SO3H acts as a nanoreactor
oxindole 5 attacks the protonated carbonyl group of 4 to give 6, which after
protonation of the hydroxyl group and loss of H2O forms the products 3.
Synthesis of N-alkyl isatin was performed by using isatin derivatives and
different alkyl halides in DMF in the presence of K2CO3 for 12–24 h (Scheme 3)
[22]. Also, N-benzyloxindole was synthesized by Wolff–Kishner reduction of N-
benzylisatin in hydrazine hydride for 1.5 h (Scheme 4) [23, 24]. The results are
summarized in Table 3.
There are only two reports of synthesis of isoindigo derivatives 3 in the literature,
as shown in Table 4. In comparison with existing methods, the present methodology
has several advantages such as greener conditions, simple synthesis, short reaction
time, easy work-up, and good yield with high product purity.
Antimicrobial activity
All synthesized compounds were screened for antimicrobial activity using the disc
diffusion method. The microorganisms used in this study were Escherichia coli
ATCC 25922 and Pseudomonas aeruginosa ATCC 85327 (Gram-negative bacte-
ria), Bacillus subtilis ATCC 465 and Staphylococcus aureus ATCC 25923 (Gram-
positive bacteria), and Candida albicans ATCC 10231, and Saccharomyces
cerevisiae ATCC 9763 (fungi). All compounds were dissolved in DMSO
(100 lg/ml), and 25 ll was loaded onto 6-mm paper discs. One hundred
microliters of 109 cell/ml suspension of the microorganisms was spread on sterile
123

Efficient green synthesis of isoindigo derivatives
H
O
O
H
H
SBA-Pr-SO3H
SBA-Pr-SO3H
N
N
O
O
O
O
N
N
H
H
H
SBA-Pr-SO3
H
SBA-Pr-SO3H
OH
O
OH2
O
4
2
1
N
N
H
H
O
OH
6
7
N
N
H
H
5
H
N
H
N
O
O
H
-H2O
SBA-Pr-SO3
O
O
N
N
H
H
8
3
Scheme 2 Proposed mechanism for the synthesis of isoindigo
O
O
R3
R3
R2Cl, K2CO3
O
O
DMF, reflux, 12-24 h
N
N
R2
H
2a-b
2f-h
Scheme 3 Synthesis of isatin derivatives
O
Scheme 4 Synthesis
of N-benzyloxindole from
N-benzylisatin
N2H4, OH
O
O
reflux, 1.5 h
90%
N
N
2f
1b
Table 3 Reaction times and yields of N-alkylation of isatins
Entry
Numbers
R2
R3
Time (h)
Yield (%)
Mp (°C)
Mp (lit.)
1
2
3
2f
CH2Ph
H
12
24
24
85
80
70
131–133
88–91
130–132 [22, 23]
87–90 [25]
2g
2h
CH2CH=CH2
CH2Ph
H
Br
147–150
152 [26]
Mueller–Hinton agar plates, and the discs were placed on the surface of culture
plates. The minimum inhibitory concentration (MIC) of the selected compounds
which showed antibiotic activity in disc diffusion tests was also determined by
microdilution method [28] and compared with three commercial antibiotics:
chloramphenicol, gentamicin, and nystatin. Table 5 presents the inhibition zones of
compounds around the discs. None of the compounds showed antibiotic activity
123

P. Gholamzadeh et al.
Table 4 Comparison of different conditions for synthesis of isoindigo derivatives
Entry
Catalyst
Solvent
Condition
Time
Yield (%)
Year
1
2
3
SBA-Pr-SO3H
–
140 °C
95 °C
MW/200 °C
1 h
85
90
91
This work
2001 [27]
20091
HCl concentration
HCl concentration
AcOH
AcOH
3 h
30 min
Table 5 Antimicrobial activities of isoindigo derivatives against some Gram-positive and Gram-nega-
tive bacteria and fungi, as determined by disc diffusion (IZ = 250 lg/disc) and MIC methods
3a
3b
3c
3d
3e
3f
3g
IZ MIC IZ MIC IZ MIC IZ MIC IZ MIC IZ MIC IZ MIC
B. subtilis (ATCC
465)
0
9
0
0
0
0
–
10 256 13 128
0
0
0
0
0
0
–
–
–
–
–
–
9
9
0
0
0
0
512
16 32
0
0
0
0
0
0
–
–
–
–
–
–
S. aureus (ATCC
25923)
512 10 256 16 32
1024 13 256
E. coli (ATCC
25922)
–
–
–
–
0
0
0
0
–
–
–
–
0
0
0
–
–
–
–
–
–
–
–
14 128
P. aeruginosa
(ATCC 85327)
0
0
0
–
–
–
C. albicans
(ATCC 10231)
S. cerevisiae
(ATCC 9763)
0
3h
3j
Chloramphenicol Gentamicin Nystatin
IZ MIC IZ MIC IZ
MIC
IZ MIC
IZ MIC
B. subtilis (ATCC 465)
S. aureus (ATCC 25923)
E. coli (ATCC 25922)
13 128
15 64
0
–
26
22
24
8
4
28 0.125
20 0.5
20 0.5
–
–
–
–
–
8
4
13 128
8
–
12 128
0
0
0
0
–
–
–
–
4
–
P. aeruginosa (ATCC 85327)
C. albicans (ATCC 10231)
S. cerevisiae (ATCC 9763)
0
0
0
–
–
–
256
–
18
–
1
–
–
–
–
18
23
–
–
–
against P. aeruginosa or C. albicans; hence, these compounds have narrow-
spectrum antimicrobial activity. Compounds 3f and 3i exhibited poor activity
against E. coli with inhibition zones of 14 and 12, respectively. Compounds 3f and
3c exhibited the best results against B. subtilis and S. aureus, respectively, with
inhibition zone of 16.
Relation between UV–Vis spectra of isoindigo derivatives and their biological
activities
Investigation of the UV–Vis spectrum of the isoindigo derivatives showed that N-
substituted derivatives showed a similar pattern to 3a (Chart 1, upper) whereas
123

Efficient green synthesis of isoindigo derivatives
5-substituted derivatives showed similar UV–Vis patterns (Chart 1, lower), but the
N,N0-disubstituted compound 3j showed no absorption. Chart 2 compares the UV–
Vis absorption of compounds 3b and 3e. In this work, antimicrobial activities of
5-substituted isoindigo derivatives were proved, but these groups of compounds
have no antiproliferative activities [21]. In contrast, N-substituted isoindigo
derivatives have very poor antimicrobial properties but show antiproliferative
activities in human cells [1].
Preparation of catalyst
New nanoporous silica SBA-15 can be obtained by using commercially available
triblock copolymer Pluronic P126 as a structure-directing agent [10, 11].
Functionalization of SBA-15 with –SO3H group was usually performed though
direct synthesis or postgrafting [29]. As shown in Fig. 3, the SBA-15 silica was
functionalized with (3-mercaptopropyl)trimethoxysilane (MPTS), then the thiol
groups were oxidized to sulfonic acid by hydrogen peroxide. Analysis of the catalyst
surface was performed by various methods such as thermogravimetric analysis
(TGA), Brunauer–Emmett–Teller (BET) analysis, and elemental (CHN) methods,
which demonstrated that the propyl sulfonic acids were immobilized into pores. The
Chart 1 UV–Vis spectrum of N-substituted isoindigo derivatives (left) and 5-substituted isoindigo
derivatives (right)
Chart 2 Comparison of the
UV–Vis spectra of 3b and 3e
123

P. Gholamzadeh et al.
Fig. 3 Schematic illustration of preparation of SBA-Pr-SO3H
Fig. 4 SEM (a) and TEM (b) images of SBA-Pr-SO3H
average pore diameter of the surface area was calculated by the BET method and
pore volume of SBA-Pr-SO3H are 440 m2 g-1, 6.0 nm and 0.660 cm3 g-1
,
respectively, which are smaller than those of SBA-15 due to the immobilization of
sulfonosilane groups in the pores [30, 31]. The SEM image of SBA-Pr-SO3H
(Fig. 4a) shows uniform particles of about 1 lm. The same morphology was
observed for SBA-15. It can be concluded that the morphology of the solid was
retained without change during the surface modification. On the other hand, the
TEM image (Fig. 4b) reveals parallel channels that resemble the pore configuration
of SBA-15. This indicates that the pores of SBA-Pr-SO3H did not collapse during
the two steps of the reaction.
123

Efficient green synthesis of isoindigo derivatives
Conclusions
A novel and highly efficient method for synthesis of isoindigo derivatives has been
developed based on solvent-free reaction of isatins and oxindole using recyclable
and environmentally friendly SBA-Pr-SO3H as a green heterogeneous solid acid
nanocatalyst. Antimicrobial testing of the products and comparison with UV–Vis
results proved that 5-substituted isoindigo derivatives have antimicrobial activities
but no antiproliferative properties. However, N-substituted products are good
antiproliferative compounds related to their antimicrobial activity.
Acknowledgments We gratefully acknowledge the financial support from the Research Council of
Alzahra University, the University of Tehran, and Shahid Beheshti.
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