Pulsed laser ablated zeolite nanoparticles: A novel nano-catalyst for the synthesis of 1,8-dioxo-octahydroxanthene and N-aryl-1,8-dioxodecahydroacridine with molecular docking validation

Article abstract of DOI:10.1002/aoc.5250

There is an increasing interest in the synthesis of metal nanoparticles (NPs) from bulk metals using pulsed laser ablation in liquids (PLAL), as it offers an easy and simple synthesis route. In this work, zeolite NPs (molecular sieve 4A) were successfully

Full text of DOI:10.1002/aoc.5250

Received: 2 July 2019
DOI: 10.1002/aoc.5250
Revised: 29 August 2019
Accepted: 1 September 2019
F U L L P A P E R
Pulsed laser ablated zeolite nanoparticles: A novel nano‐
catalyst for the synthesis of 1,8‐dioxo‐octahydroxanthene
and N‐aryl‐1,8‐dioxodecahydroacridine with molecular
docking validation
1
,2
1,3
4
A.M. Abdelghany
Tamer K. Khatab
| A.A. Menazea | Mansoura A. Abd‐El‐Maksoud |
4
1
Spectroscopy Department, Physics
There is an increasing interest in the synthesis of metal nanoparticles (NPs)
Division, National Research Centre, 33
ElBehouth Street, PO Box 12622, Dokki,
Giza, Egypt
from bulk metals using pulsed laser ablation in liquids (PLAL), as it offers an
easy and simple synthesis route. In this work, zeolite NPs (molecular sieve
2
Basic Science Department, Horus
4A) were successfully synthesized by the PLAL technique, and characterized
University, International Coastal Road,
New Damietta, KafrSaad, Damietta, Egypt
by X‐ray diffraction, scanning electron microscopy, Fourier transform infrared
spectroscopy, transmission electron microscopy, field emission scanning elec-
tron microscopy, and high‐resolution transmission electron microscopy. Data
obtained confirm the formation of the crystalline phase of zeolite. The synthe-
sized catalyst (zeolite molecular sieve 4A) was used as an efficient and facile
promotor for the synthesis of xanthene and acridine derivatives. Molecular
docking of the synthesized compounds was validated using quinone reductase
2 (NQO2) and acridine orange as the ligand, with the synthesized molecules
showing good drug–ligand interaction on the active site of NQO2, compared
with that of acridine orange.
3
Laser Technology Unit, National
Research Centre, 33 ElBehouth Street, PO
Box 12622, Dokki, Giza, Egypt
4
Organometallic and Organometalloid
Chemistry Department, National Research
Centre, 33‐El‐Buhouth Street, PO Box
12622, Dokki, Giza, Egypt
Correspondence
A. M. Abdelghany, Spectroscopy
Department, Physics Division, National
Research Centre, 33 ElBehouth Street, PO
Box 12622, Dokki, Giza, Egypt.
Email: a.m_abdelghany@yahoo.com
KEYWORDS
acridine, dimedone, laser ablation, nanoparticles, xanthene, zeolite
1
| INTRODUCTION
in small bags for use in packaging of desiccant foods,
electronic components, and drugs. It is also used for dry-
Zeolite is a microporous and aluminosilicate mineral
used as a molecular sieve and as an adsorbent of several
ing and removing of CO from natural gas, liquefied
2
petroleum gas, or air, and for the removal of hydrocar-
bons, ammonia, and methanol from gas streams (ammo-
nia syn gas treating) and for dehydration of refrigeration
systems and air streams in the air‐break units of buses,
2+
+
+
2+ [1]
cations, such as Ca , K , Na , and Mg . It is also
applied in the modification of several bioreactor
[2]
devices. Zeolite (molecular sieve 4A) is an alkali metal
aluminosilicate. Molecular sieve 4A is the sodium form
of the type A crystal structure of zeolite, and can adsorb
molecules with diameters smaller than 4 Å (0.4 nm).
Zeolite (molecular sieve 4A) is produced by the reac-
tion of water, sodium silicate, sodium aluminate, and
sodium hydroxide. Molecular sieve 4A is usually packed
[
3–6]
trucks, and locomotives.
In recent years, nanoparticles (NPs) have attracted
wide attention due to their excellent physical and chem-
ical properties and appear promising in the field of
[
7–11]
material science.
Subjecting metal NPs to pulsed
laser ablation of solids in liquids environment (PLAL)
Appl Organometal Chem. 2019;e5250.
wileyonlinelibrary.com/journal/aoc
© 2019 John Wiley & Sons, Ltd.
1 of 9
https://doi.org/10.1002/aoc.5250

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ABDELGHANY ET AL.
is one of the promising routes to obtain metal colloids.
PLAL has received much attention as a novel technique
for synthesizing NPs. NPs of various species of materials
such as metals, metal oxides, semiconductors, and
organic materials can be obtained by irradiating intense
nanosecond laser onto these materials settled in sol-
Sigma‐Aldrich and used without further purification.
Deionized water was used as the solvent media for laser
ablation.
[12–14]
vents.
This is a fast, simple, straightforward, and
2.1.2 | Synthesis of zeolite 4A nanoparti-
easy method to prepare NPs compared with other
methods.
cles by PLAL
Several methods for producing xanthenes and acri-
dines have been reported in the literature, as these
organic compounds exhibit a wide range of pharmaceuti-
cal activity and have industrial and synthetic applica-
Zeolite NPs were prepared by PLAL. First, a zeolite plate
(
target) of high purity (99.99%; dimensions: 10 mm diam-
eter and 3 mm thickness) was placed at the bottom of a
beaker filled with 30 ml deionized water solution. The
height of the solution was 1.5 cm from the target plate.
The target was irradiated with Nd:YAG nanosecond
pulsed laser (PRII 8000 Continuum laser; Electro–optics,
Inc.) under the following conditions: fundamental wave-
length of 1064 nm with 4 W power, 10 Hz pulse repetition
rate, and 7 nm pulse width for 20 min. The laser beam
was incident perpendicularly on the surface of the plate
target after focusing it through a 10‐cm focal length con-
vex lens to achieve laser ablation on the surface of the
target.
[15–23]
tions.
Catalytic condensation of dimedone and
variable aldehydes is a common method for the synthesis
[
24]
of xanthenes such as polyphosphoric acid (PPA)–SiO
2,
[25]
[26]
[27]
SbCl –SiO
silica sulfate,
NaHSO ·SiO
and
3
2,
4
2,
[28]
ZrOCl ·8H O.
By contrast, acridines could be synthe-
2
2
sized by mixing aromatic aldehydes, dimedone, and nitro-
[
29]
[30]
gen sources such as urea,
acetate,
aniline,
ammonium
[31]
[32]
hydroxyl amines,
ammonium hydroxide,
The aforesaid syntheses
[
33]
and ammonium bicarbonate.
reactions have been achieved using various catalysts such
as amberlyst‐15,2,3–Dicyano–1,4–hydroquinone (DCH),
[
34]
[35]
DBH ; Nano CeO2 ; ammonium chloride or L‐
[36]
[37]
proline, Zn(OAc) ·2H O ; nano‐Fe O @SiO ‐SO H
;
2
2
3
4
2
3
[40]
2
−
[38]
[39]
SO4 /ZrO2 ; ionic liquids ; b‐cyclodextrin ; and
imidazolium salts with perfluoroalkyl tails such as
2.1.3 | Characterization
[41]
Bronsted acid.
Unfortunately, most available methods
have many disadvantages, such as the use of corrosive,
expensive, and not easily available reagents and require
drastic reaction conditions such as refluxing, strong acidic
medium, and fatiguing Reaction work‐up boundaries.
To overcome these disadvantages, we herein propose a
catalytic synthesis of xanthenes and acridines over an
efficient and recyclable catalyst, zeolite (molecular sieve
The crystalline structure of samples was characterized
using PANalytical X’Pert Pro XRD diffractometer system
with Cu‐Kα radiation (λ = 0.154 nm) operating at
45 kV. All scans were performed over a 2θ range from
4° to 80° under UV–Vis light. Optical measurements were
studied as a function of wavelength λ (nm) of the pre-
pared samples and measured using a JASCO (V‐570)
UV/VIS/NIR double‐beam spectrophotometer at room
temperature at the wavelength region between 200 and
1000 nm.
4
A), which was prepared by a novel method (laser abla-
tion). The obtained structures of xanthenes, acridines,
and zeolite were characterized and analyzed by scanning
electron microscopic (SEM) measurements, X‐ray diffrac-
tion (XRD) scans, and Fourier transform infrared (FT‐IR)
spectra.
FT‐IR was used to demonstrate the chemical composi-
tion of samples prepared. FT‐IR spectral data were col-
−
1
lected through 32 scans with resolution of 2 cm using
a single‐beam spectrometer (Nicolet iS 10) via the KBr
powder route at wavenumbers between 4000 and
−
1
2
2
2
| EXPERIMENTAL
.1 | Catalyst preparation
.1.1 | Materials
400 cm and their structures examined. The morphology
and topography of the samples prepared were analyzed by
field emission scanning electron microscopy (FE‐SEM;
Quanta FEG 250) and high‐resolution transmission elec-
tron microscope (HR‐TEM; JEOL‐JEM‐1011). Synthesized
Materials was investigated by energy‐dispersive X‐ray
spectroscopy using the software (TEAM) built into the
scanning electron microscope (Quanta FEG 250 electron
microscope).
Zeolite [molecular sieve 4A; CAS No.: 1318‐02‐1; chemi-
cal formula: Na O·Al O ·2SiO ·4, 5H O, silica‐to‐alumina
ratio (SiO /Al O )
2
2
3
2
2
≈
2] was purchased from
2
2 3

ABDELGHANY ET AL.
3 of 9
2.2 | Chemicals apparatus
2 s, O‐CH
2
‐O), 5.85–6.64 [m, Ar (3H)], 7.07–7.08 [d,
1
3
J = 5 Hz, Ar (2H)], 7.46–7.47[d, J = 5 Hz, Ar(2H)], C‐
The nuclear magnetic resonance (NMR) instrument used
for the illustration of organic compounds was Joel
NMR (100 MHz, CDCl ) δ = 27.2–55.4 (11 aliphatic C),
3
101.25 (O‐CH ‐O), 109.54–159.43 [4C = (Olefinic) + 12C
2
5
00 MHz spectrometer in CDCl . The measuring unit of
Ar], 194.44 (C=O), 197.71 (C=O). MS (EI) m/z (%): 505
3
+
+
chemical shifts (δ) is parts per million (ppm). Mass spec-
tra were recorded on an Agilent LC–MS spectrometer
(20) [M + 2]; 503 (23) [M ]. Anal. calcd. For.
C H ClNO ; (503.93); C, 71.49; H, 5.99; N, 5.90; Found:
30
30
4
(
pump quaternary 1200 Series; quadruple MSD 6110).
Reaction monitoring by thin‐layer chromatography
TLC) was performed on Merck silica gel GF254 plates
C, 71.45; H, 5.96, N, 5.87.
(
3
3
| RESULTS AND DISCUSSION
and visualized by UV light (254 nm). All chemicals were
obtained from Sigma‐Aldrich.
.1 | Characterization of synthesized nano
zeolites
2
.2.1 | Structure elucidation and general
3.1.1 | XRD experimental data
procedure
Figure 1 illustrates the XRD patterns of synthesized zeo-
lite 4A NPs that show several sharp peaks at 7.16, 10.27,
1
. A mixture of aldehydes (1 mmol), dimedone (2 mmol),
and modified to (ZNps, 10 mol%) was stirred at 60–70 °C.
The reaction mixture was followed by TLC until the sub-
strates disappeared. Chloroform (20 ml) was used to
extract the organic product and the pure products were
obtained after recrystallization.
12.44, 16.05, 21.60, 24.50, 27.3. 30.00, and 34.30 (degree)
which are assigned to their corresponding Miller indices
(
hkl) reflection planes of the cubic crystalline system pre-
[
42]
viously indexed by Zamani et al.
et al.
and Hasegawa
[
42,43]
2
. A mixture of aldehydes (1 mmol), dimedone
Zeolite 4A shows the same previously assigned pat-
tern, which indicates that its structure is well preserved
even after pulsed laser ablation.
(
(
2 mmol), various anilines (1 mmol), and modified to
ZNps, 10 mol%) was stirred at 60–70 °C. The reaction
mixture was followed by TLC until the substrates disap-
peared. Chloroform (20 ml) was used to extract the
organic product.
3.1.2 | Fourier transform‐infrared spectra
Figure 2 shows the FT‐IR‐normalized absorption spec-
trum of zeolite 4A samples with the following features:
2
.2.2 | Structure elucidation data of new
compounds
−
1
1
. A sharp band at 455 cm , which is assigned to inter-
1
0‐(Benzo[d][1,3]dioxol‐5‐yl)‐3,4,6,7‐tetrahydro‐9‐(3‐pyr-
nal vibrations of (Si–O) and (Al–O) bending.
idyl)‐3,3,6,6
tetramethylacridine‐1,8(2H,5H,9H,10H)‐
dione (5d)
−
1
1
IR (KBr): 1620 (C=O), 1615 (C=O) cm , H‐NMR
(
400 MHz, CDCl ) δ ppm: 0.96–1.04 (s, 4CH ), 2.16, 2.20
3
3
(
s, 2CH ), 2.47 (d, CH), 2.50 (d, CH), 4.95 (s, CH), (5.90,
2
5
9
.92, 2 s, O‐CH ‐O), 6.07–8.20 [m, Ar (7H), CH = enolic],
2
13
.29 (s, OH enolic),
C‐NMR (100 MHz, CDCl3)
δ = 27.25–55.44 (10 aliphatic C), 101.25 (O‐CH ‐O),
2
1
1
11.13–160.43 [6C = (Olefinic) + 10C Ar],197.84 (C=O),
98.55 (C=O). MS (EI) m/z (%): 470 (10) [M ]; Anal.
+
calcd. For: C H N O ; (470.57); C, 74.02; H, 6.43; N,
29
30 2 4
5
.95. Found: C, 73.98; H, 6.38; N, 5.90%.
1
0‐(Benzo[d][1,3]dioxol‐5‐yl)‐9‐(4‐chlorophenyl)‐3,4,6,7‐
tetrahydro‐3,3,6,6‐tetramethylacridine‐
,8(2H,5H,9H,10H)‐dione (5e)
IR (KBr): 1630 (C=O), 1626 (C=O) cm , H‐NMR
1
−
1
1
(
500 MHz, CDCl ) δ ppm: 1.11–1.25 (s, 4CH ), 2.18, 2.22
FIGURE 1 X‐ray diffraction patterns of synthesized zeolite 4A
3
3
(
s, 2CH ), 2.38, 2.50 (s, 2CH ), 5.14 (s, CH), (5.85, 5.88,
nanoparticles
2
2

4
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ABDELGHANY ET AL.
silicon and aluminum atoms linked to the oxygen
molecule.
–
1
4
. A band centered at about 3460 cm , along with that
−
1
at 1665 cm , both of which are related to OH
groups.
3.1.3 | Scanning electron microscopy
Figure 3 shows the SEM micrograph of zeolite 4A sam-
ples after being treated with the laser beam. The figure
reveals the presence of truncated‐side cubic crystals
with a size of about 25 nm, as calculated using the
Debye–Scherrer equation and observed to be compatible
with that observed on
a
transmission electron
microscope.
FIGURE 2 Fourier transform‐infrared‐normalized absorption
spectrum of zeolite 4A
Figure 4 shows the SEM mapping analysis of zeolite
A4 samples studied. The obtained image reveals a
homogenous distribution of all analyzed partner ele-
ments (Na, Mg, Al, Si, Ca, and O atoms) in their chem-
ical structure (listed in Table 1 along with their atomic
and weight percentages). Silica was the main
−
1
2
3
. A sharp band at 554 cm , which is assigned to the
external vibration of double four rings.
. A sharp intense band at 1010 cm , which is attrib-
uted to asymmetric stretching vibrations of both
−
1
FIGURE 3 Scanning electron microscopy image (inset) with energy‐dispersive X‐ray analysis spectrum of zeolite 4A
FIGURE 4 Scanning electron
microscopy mapping of zeolite 4A

ABDELGHANY ET AL.
5 of 9
TABLE 1 Energy‐dispersive X‐ray analysis of studied sample
makes them an important scaffold in many
pharmaceutical applications. Xanthene derivatives, acri-
dine derivatives, 1,4‐dihydropyridine derivatives, and
quinolone derivatives are good precursors in both
organic synthesis and discovery of a new pharmaceuti-
cal substance.
Element
Na
MgO
Al
SiO
CaO
Weight %
Atomic %
2
O
4.86
2.42
5.27
4.02
2
O
3
31.07
43.49
18.16
20.44
48.55
21.72
Our group has developed many novel green method-
ologies for organic synthesis and transformations of
2
[
44–47]
compounds.
In continuation of our previous
work, we report herein an efficient, facile, and
powerful protocol for the one‐pot synthesis of 1,8‐
dioxodecahydroxanthenes
(3a–3g)
and
1,8‐
constituent, with lime and alumina comprising the
major percentage, and soda and magnesium oxide con-
stituting only a minor percentage.
dioxodecahydroacridines (5a‐5e) using zeolite 4A NPs
as a catalyst in aqueous reaction conditions. The synthe-
sis involved the following steps:
1
. A catalytic amount(10 mol%) of zeolite 4A NPs for
an appropriateperiod(10–120 mins) prepared by
treating, in deionized water, an aromatic aldehyde
with 2 mol of dimedone in the presence of a
3
.1.4 | Transmission electron microscopy
Figure 5 shows TEM images with nearly homogenous
spherical morphology. The average size of samples
obtained from these observations ranges between 19 and
2
5 nm that matches well with that calculated from XRD
experimental data. Furthermore, the selected area diffrac-
tion pattern of prepared nanocrystals shows a combined
pattern of concentric rings and sharp bright spots over
the rings, indicating a crystalline structure supporting
XRD data.
TABLE 2 Synthesis of 1,8‐dioxo‐octahydroxanthenes using vari-
ous aldehydes
Time Yield
Entry
R
1
Product (min) (%)
1
2
3
4
5
6
7
Phenyl
3a
3b
3c
3d
20
60
80
60
60
70
90
60
70
3
.2 | Organic synthesis
4‐Methoxyphenyl
4‐Chlorophenyl
4‐Fluorophenyl
90
Multicomponent reactions are powerful strategies to syn-
thesize important heterocyclic compounds with various
important biological properties in an easy way using
available materials.
90
4‐N,N‐dimethylaminophenyl 3e
30
3‐Pyridyl
3f
120
60
The molecularly diverse structure of polynuclear
5‐Nitro‐2‐furyl
3g
and
complex
heterocyclic
organic
compounds
FIGURE 5 Transmission electron microscopy images, selected area diffraction pattern, and high‐resolution image

6
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ABDELGHANY ET AL.
SCHEME 1 Synthesis of 1,8‐dioxo‐octahydroxanthenes. NP,
nanoparticle
SCHEME
dioxodecahydroacridines
2
Four‐component
synthesis
of
N‐aryl‐1,8‐
catalytic amount of zeolite 4A NPs for an appropri-
ate period. Upon formation of the final product, the
reaction mixture was cooled down to room temper-
ature and the catalyst filtered off using ethanol. The
reaction was explored to understand the catalytic
3.3 | Molecular docking studies
In recent decades, molecular docking has become a
progressively significant tool for drug discovery, as
it can predict theoretically the interaction between a
mechanism
responsible
for
producing
[
48–55]
octahydroxanthenediones in high yield. Table 2
and Scheme 1 summarize the structures of the prod-
ucts, melting points, yield percentages, and reaction
times for compounds 3a–3g.
. N‐aryl‐1,8‐dioxodecahydroacridine derivatives were
synthesized in a one‐pot reaction using four compo-
nents. The reaction was started by reacting 1 mol of
aromatic amines and aromatic aldehydes and 2 mol
of dimedone in the presence of a catalytic amount
of zeolite NPs in deionized water at 70–80 °C. Within
drug and a protein.
computational strategies to permeate all aspects of
drug discovery, including virtual screening
Such a method allows
techniques, which are more direct and low in cost, com-
pared with traditional experimental high‐throughput
screening.
2
Based on the standard docking protocol and using
[
48]
MOE 2015.10 software,
the docking between the syn-
thesized 1,8‐dioxo‐octahydroxanthene (3a–3g) and N‐
aryl‐1,8‐dioxodecahydroacridine (5a–5e) compounds
was validated using quinone reductase 2 (NQO2) as an
inhibitor. For comparison, another reaction was per-
formed using the same reactants, but with acridine
orange as a ligand instead of NQO2. Historically,
NQO2 was classified as a detoxification enzyme respon-
sible for the reduction of potentially cytotoxic qui-
10–30 min, N‐aryl‐1,8‐dioxodecahydroacridines (5a–
5e) are produced. The overall results are described in
Table 3 and Scheme 2.
The proposed mechanism for the catalytic synthesis of
octahydroxanthenediones is presented in Scheme 3. The
aldehyde carbonyl group was polarized by the catalyst
which facilitates the nucleophilic attack of C‐2 of the
enolized dimedone molecule, followed by that of another
dimedone molecule to form intermediate I. This interme-
diate was then activated by the catalyst, which subse-
quently participates in another nucleophilic attack
involving the lone pair of electrons of the OH group. Fol-
lowing the nucleophilic attack, dehydration occurred to
produce the 1,8‐dioxo‐octahydroxanthene II.
[
49]
nines.
In the presence of NQO2, the docking of the
synthesized molecules occurred through the drug–ligand
interaction on the “A” binding site in NQO2. The
obtained results and the calculated binding energy
score in kilocalories/mole (kcal/mol) are summarized
in Figures 6–8. Data obtained show that the binding
sites in the targeted enzyme (NQO2) are attractive for
the synthesized molecules, compared with those in the
common ligand (acridine orange).
TABLE 3 Reaction of various anilines, various aldehydes, and dimedone
Entry
R
1
R
2
Products
Time (min)
Yield (%)
1
2
3
4
5
3(MeO)Ph
4(Cl)Ph
4(F)Ph
Ph
5a
5b
5c
5d
5e
20
20
10
25
30
95
90
92
78
75
Ph
Ph
3‐Pyridyl
4(Cl)Ph
3,4‐Methylendioxyphenyl
3,4‐Methylendioxyphenyl

ABDELGHANY ET AL.
7 of 9
SCHEME 3 Proposed reaction mechanism
FIGURE 6 Calculated binding energy
scores in kilocalories/mole (kcal/mol).
The red point corresponds to acridine
orange (reference sample) and black
points to synthesized xanthenes and
acridines
FIGURE 7 Two‐dimensional interaction between pockets in quinone reductase 2 and 3g, compared with that between 3g and acridine
orange

8
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ABDELGHANY ET AL.
FIGURE 8 Three‐dimensional interaction between pocket in quinone reductase 2 and compound 3g with the hydrogen bond length
indicated
[
7] M. A. Morsi, A. Rajeh, A. A. Menazea, J. Mater. Sci. Mater.
Electron. 2019, 30(3), 2693.
4
| CONCLUSIONS
Zeolite NPs (molecular sieve 4A) were successfully pro-
duced by the PLAL technique. The potential of the het-
erogeneous catalyst (zeolite 4A NPs) was examined and
characterized by FT‐IR, XRD, FE‐SEM, and HR‐TEM.
The catalyst zeolite 4A was then used for the synthesis
of xanthene and acridine derivatives. The zeolite NPs
proved to be an efficient, facile, and eco‐friendly catalyst
for the one‐pot synthesis of 1,8‐dioxo‐octahydroxanthenes
and 1,8‐dioxo‐octahydroacridines. Furthermore, results of
molecular docking studies indicated that most synthe-
sized molecules showed good drug–ligand interaction on
the active site of NQO2, compared with that of acridine
orange.
[8] I. S. Elashmawi, A. A. Menazea, J. Mater. Res. Technol. 2019,
(8), 1944.
2
[9] F. H. Abd El‐kader, N. A. Hakeem, W. H. Osman, A. A.
Menazea, A. M. Abdelghany, Silicon 2019, 11(1), 377.
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How to cite this article: Abdelghany AM,
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Pulsed laser ablated zeolite nanoparticles: A novel
nano‐catalyst for the synthesis of 1,8‐dioxo‐
octahydroxanthene and N‐aryl‐1,8‐
dioxodecahydroacridine with molecular docking
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