Design, synthesis, and anticancer activities of sodium quinazolin-4-diselenide compounds

Article abstract of DOI:10.1002/jhet.3743

Substituted 4-chloroquinazoline reacted with sodium diselenide to give novel sodium quinazoline-4-diselenide compounds. The reaction provides an efficient and facile approach to the synthesis of sodium quinazoline-4-diselenide compounds. Structures of title compounds were confirmed by IR, ¹H NMR, ¹³C NMR, and elemental analysis. MTT assay was adopted to show anticancer activities of the compounds. Compounds 5a and 5h showed good activities against cancer-cell lines MDA-MB-435, MDA-MB-231, A549, SiHa, and HeLa. In addition, 5a exhibited quite good anticancer effects on relative above cell lines with 10μM concentration compared with oxaliplatin and gefitinib of the commercial anticancer drugs.

Full text of DOI:10.1002/jhet.3743

Inorganic Chemistry Communications 101 (2019) 145–149
Contents lists available at ScienceDirect
Inorganic Chemistry Communications
journal homepage: www.elsevier.com/locate/inoche
Short communication
A new supramolecular compound based on Keggin-type phosphomolybates
with mixed-ligand and mixed-valence Cu(I/II): [Cu(I)(phen) ] {[Cu
2
2
VI
V
(
II)] (phen) PTA}[H PMo Mo O ]
2
4
3
8
4
40
a,⁎
a
a
a
a
b
a
Yu-nan Zhang , Liang Chang , Li-xin Liu , Xin Su , Miao Huang , Xue-song Zhang , Lei Zhang ,
a
a
Yun-jie Zhang , Da-jun Zhang
a
b
College of pharmacy, Jiamusi University, Heilongjiang Province, Jiamusi 154007, China
First Affiliated Hospital of Jiamusi University, Heilongjiang Province, Jiamusi 154007, China
G R A P H I C A L A B S T R A C T
A R T I C L E I N F O
A B S T R A C T
Keywords:
With an aim to obtain
a
new supramolecular compound based on Keggin-type polyoxometalates
V
VI
8
Keggin-type phosphomolybates
Mixed-ligand
with mixed-ligand: [Cu(I)(phen) ] {[Cu(II)] (phen) PTA}[H PMo Mo
O
40
]
(phen = 1,10-phenanthroline,
2
2
2
4
3
4
PTA = terephthalic acid) has been synthesized under hydrothermal conditions and structurally characterized by
Mixed-valence
elemental analyses, IR, X-ray single crystal diffraction, TG analyses and XPS. In the title compound, the Keggin-
Helical chain
+
type phosphomolybates anions, butterfly-shaped [Cu(I)(phen)
2
]
subunits and dumbbell-shaped {[Cu
Electrocatalytic property
2
+
(
II)]
2
(phen)
4
PTA} subunits are alternately connected to form chiral helical chains via hydrogen bonds along b
+
axis, and the adjacent chiral helical chains are connected in the way of sharing butterfly-shaped [Cu(I)(phen) ]
2
2
+
subunits and dumbbell-shaped {[Cu(II)]
2
(phen)
4
PTA}
subunits to form 3D supramolecular reticular frame-
work. As expected, the title compound with mixed-ligands (phen and PTA) has been successfully synthesized,
+
inconceivably, the title compound also contains mixed-valence Cu (Cu(I) in butterfly-shaped [Cu(I)(phen) ]
2
2
+
subunits; Cu(II) in dumbbell-shaped {[Cu(II)]
2
(phen)
4
PTA}
subunits). The preliminary analyses show that
mixed-valence Cu(I/II) may be due to the reduction of Cu(II) (from CuCl
2
) to Cu(I) (in butterfly-shaped [Cu(I)
+
(
phen)
2
]
subunits) by N-containing compound. The successful results of this work provide a new idea that
supramolecular materials with attractive structures and novel properties, which could be designed and
⁎
Corresponding author.
E-mail address: zhangyunan@jmsu.edu.cn (Y.-n. Zhang).
https://doi.org/10.1016/j.inoche.2019.01.037
Received 2 December 2018; Received in revised form 24 January 2019; Accepted 25 January 2019
Available online 26 January 2019
1387-7003/ © 2019 Elsevier B.V. All rights reserved.

Y.-n. Zhang et al.
Inorganic Chemistry Communications 101 (2019) 145–149
synthesized by introducing of mixed-ligands into the supramolecular materials. Additionally, the electrocatalytic
property of the title compound to H
2
2
O has been studied.
Supramolecular chemistry has been defined as the understanding of
compound based on Keggin-type phosphomolybates containing mixed-
ligand and mixed-valence Cu(I/II) with helical chains: [Cu(I)
intermolecular interactions in the context of crystal packing and shown
spectacular advances in the last couple of decades as a consequence of
their interesting structural chemistry and unusual properties [1–4].
Hereinto, the organic-inorganic hybrid supramolecular materials have
received extremely intensive interest, because inorganic components
could combine with organic components to obtain unusual structures
and inconceivable properties [5,6]. Polyoxometalates (POMs), as one
kind of well-known inorganic components with nucleophilic oxygen-
enriched surfaces and oxygen atoms on the surface forming hydrogen
bonds with organic components, could be viewed as important in-
organic building blocks for constructing organic-inorganic hybrid ma-
terials [7–10]. So the syntheses of organic-inorganic hybrid materials
based on POMs are very significant. Usually, a promising tool for these
materials' design is the evaluation and use of organic ligands under
hydrothermal conditions, such as POM-based metal-organic frame-
works (POM-MOFs) [11–16]. Inspired by POM-MOFs, POMs and mixed-
ligand coordination metal ions might be introduced into the organic-
inorganic hybrid supramolecular to get attractive structures and novel
properties. Therefore, it remains a formidable challenge to rationally
design the organic-inorganic hybrid supramolecular material based on
POMs and mixed-ligands with affecting its structure and properties.
Hence, a motivation for providing a new inspirational method to
design and synthesize organic-inorganic hybrid supramolecular mate-
rials based on POMs with distinctive structure and properties by in-
troducing mixed-ligands coordinated metal ions has been put forward.
Then, Keggin-type phosphomolybates, mixed-ligands (PTA and phen)
VI
V
(phen)
2
]
2 2
{[Cu(II)] (phen)
4
PTA}[H
3
PMo
8
Mo
4
O
40
]
has been ob-
tained and characterized. In addition, the structure characteristics,
formation of mixed-valence and the electrocatalytic to H
2
O of the title
2
compound were also discussed.
All reagents were purchased commercially and used without further
purification. Elemental analyses (C, H and N) were performed on a
Perkin-Elmer 2400 CHN Elemental Analyzer. IR spectra were recorded
−
1
in the range of 400–4000 cm
on a VERTEX-70 Fourier FT-IR spec-
trophotometer with pressed KBr pellets. Thermogravimetric analyses
(TGA) were recorded on a Mettler TGA/SDTA851e thermal analyzer
−
1
under dynamic nitrogen atmosphere with a heating rate of 10 °C·min
.
X-ray powder diffraction (XRPD) patterns of samples were recorded
with a Rigaku D/max-III-B (Tokyo, Japan) diffractometer with Cu K
α
irradiation (λ = 1.54178 Å). The X-ray photoelectron spectra (XPS) of
the title compound were obtained with an X-ray photoelectron spec-
trometer (ESCALAB 250Xi, Thermo Scientific). Crystal data for the title
compound was collected on Bruker SMART-CCD diffractometers, with
Mo-K
α
monochromated radiation (λ = 0.71073 Å) at 296 K. The
structures were solved by directed methods and refined by using the
2
SHELXTL (full-matrix least-squares on F ) and Olex2 1.2 programs
packages. All the atoms (not including hydrogen atoms) were refined
anisotropically. The positions of hydrogen atoms on carbon atoms were
generated geometrically. The crystal data and structure refinements of
the title compound are summarized in Table S1. Selected bond lengths
and angles are listed in Table S2.
and CuCl
2
have been chosen in the present experiment. The following
The title compound was synthesized by the hydrothermal method
points are taken into consideration: (1) The Keggin-type POMs with
abundant surface oxygen atoms are coordination potential sites for
hydrogen bonds towards surface hydrogen atoms of organic ligands in
all directions [17–19]. (2) The copper ions have different coordination
numbers (4 or 6) and could easier coordinate with the O, N, S atoms of
the organic ligands [20,21]. (3) On the one hand, phen with a good π-
electron conjugated system is also an indispensable factor for the con-
struction of aryl stacking supported supramolecular structures [22,23],
on the other hand, PTA has a linear ribbon structure with four terminal
O atoms, flexible coordination fashion and excellent coordination
ability [24,25]. As expect, an organic-inorganic hybrid supramolecular
from
a
mixture of (NH
4
)
6
M
O7
O
2
24·4H O
(1 mmol), CuCl
2
·2H O
2
(1 mmol), phen (1 mmol), PTA (1.5 mmol), H
3
PO (0.02 mmol), NaOH
4
(1 mmol) and H O (0.83 mmol) in a molar ratio 1:1:1:1.5:0.02:1:0.83.
2
The resulting suspension was stirred for 2–3 h, then sealed in a telfon-
lined reactor with 75% filling and heated at 180 °C for 7 days. After
slow cooling to room temperature over a period of 24 h, black like block
crystals were filtered, washed with water, and dried at room tempera-
ture. Yield: 43% based on Mo. Calcd for the title compound
104
C H
4
68Cu Mo12
N O44P (3238.): C, 33.92; H, 1.74; N, 5.19. Found: C,
16
−1
28.93; H, 1.74, N, 5.19. IR (KBr pellet, cm ): 3072(m), 1946(m),
1629(m), 1522(m), 1431(m), 1346(m), 1311(w), 1226(w), 1149(w),
Fig. 1. Ball/stick representation of the asymmetric unit of the title compound.
146

Y.-n. Zhang et al.
Inorganic Chemistry Communications 101 (2019) 145–149
1
110(m), 1062(s), 965(s), 722(s) (Fig. S1).
1
00 mg graphite powder and ca. 20 mg (the title compound sample)
were mixed and ground together by agate mortar and pestle to achieve
an even, dry mixture. The mixture 0.2 mL nujol was added and stirred
with a glass rod. Then the homogenized mixture was used to pack 3 mm
inner diameter glass tubes, and the surface was wiped with weighing
paper. Electrical contact was established with copper rod through the
back of the electrode.
Single-crystal X-ray diffraction analysis reveals that the title compound
+
consists of [Cu(I)(phen)
2
]
subunits (abbreviated to Cu1 subunit), {[Cu
2
+
(
II)]
2
(phen)
4
PTA}
subunits (abbreviated to Cu2 subunit) and
polyoxoanion (abbreviated to PMo12) (Fig. 1).
V
VI
4−
[
H
3
PMo
4
Mo
8
O ]
40
Within the Cu1 subunit, the Cu(I) is four-coordinated by phen N-donors.
The Cu2 subunit structure consists of two Cu(II) ions, four phen molecules
and one PTA molecule, the Cu(II) is six-coordinated by two N-donors of
phen and of O-donors PTA. Cu1 subunits, Cu2 subunits and PMo12 clus-
ters are alternately connected to form chiral helical chains via hydrogen
bonds along b axis. The adjacent chiral helical chains are connected in way
of sharing butterfly-shaped Cu1 subunits and dumbbell-shaped Cu2 sub-
units to form 3D supramolecular reticular framework, which reveals that
the intermolecular hydrogen bonds play vital role to construct the higher
dimensional framework (Fig. 2). The bond distance of Cu9eN is 2.068,
Fig. 3. TGA curve of the title compound.
Two Cu(II) ions, four phen molecules and two PTA molecules are
combined to form dumbbell-shaped Cu2 subunits. The helical direction
of the helical chain is determined by the Cu2 subunits. Then Cu1 sub-
units and Cu2 subunits are connected to each other along b axis, which
are supported by π…π stacking interactions. In this way, an interesting
chiral helical chain is formed along b axis.
1
.995, 2.213, 2.006 and 2.011 Å for Cu9eN1, Cu9eN2, Cu9eN6,
Cu9eN7, and Cu9eO19, respectively. The PeO distances are in the range
of 1.435(7)–1.650(8) Å with an average bond length 1.529 Å, while the
OePeO angles vary from 63.9(4)° to 111.3(4)°. Relevant MoeO bonds can
be classified into three groups, MoeO
t
bonds, MoeOb/c bonds and MoeO
a
bonds, and the bond distances fall in the ranges of 1.649(5)–1.657(4) Å,
The thermal weight of the title compound is shown in Fig. 3. For the
title compound, TGA shows that weight loss start at 100 °C and ends at
1
.770(8)–1.911(5) Å, and 2.358(7)–2.442(8) Å, respectively. The distance
of hydrogen bonds is presented in Table S3.
4
00 °C. The first weight loss is in the temperature range of 100–260 °C,
It is interesting that there are different valence of copper ions in the
title compound. Within butterfly-shaped Cu1 subunit, Cu(I) is co-
ordinated by four N atoms of PTA molecules. Cu(II) is six-coordinated
by four N atoms of PTA molecules and two O atoms of phen molecule.
which is corresponding to the release of phen ligand in the title com-
pound (calc 39.15%). The second weight loss at 390 °C is ascribed to
PTA ligands (calc 4.46%). At last, the total weight loss is 45.52% (calc
Fig. 2. View of the H-bonding interactions
among the PMo12, Cu1 subunits and Cu2
subunits in the supramolecular layered fra-
mework of the title compound. The H-
bonding interactions are indicated by blue
dotted lines. (For interpretation of the re-
ferences to color in this figure legend, the
reader is referred to the web version of this
article.)
147

Y.-n. Zhang et al.
Inorganic Chemistry Communications 101 (2019) 145–149
Fig. 6. The cyclic voltammograms of title compound in 1 mol/L H
2
SO solu-
4
Fig. 4. Showing the bulk product are in good agreement with the calculated
tions at different scan rates (20, 50, 110, 140, 170 and 200 mV/s).
patterns based on the results from single-crystal X-ray diffraction.
4
3.61%), which is consistent with the molecular formula of the title
compound.
As shown in the Fig. 4, the title compound has a strong diffraction
peak in the range of 5–50°. The measured data of the title compounds
are in agreement with the peak pattern of the single crystal simulated
data, and the characteristic peak positions are in agreement, indicating
that the title compound is a pure phase.
For the title compound, the main chemical constituents of the
cluster anion were determined by XPS measurements. According to
referring to the XPS manual [26], the MoeO inner binding energy of
5
+
5+
Mo 3d3/2 and Mo 3d5/2 are 233.9 eV and 231.0 eV, respectively,
5
+
PeO bond in P 2p3/2 inner electron binding energy is 133.1 eV.
The bond valence sum calculations (BVS) indicate one out of three Cu
atoms are in the +1 oxidation state in compound [27], four out of twelve
Mo atoms are in the +5 oxidation state for compound. Hence, addition of
three protons is necessary to balance the charge of compound in the mo-
lecular formula, which are supported by the XPS measurements (Fig. 5).
Cyclic voltammetry (CV) was used to test electrocatalytic reduction
−
1
of activity for H
2
O
2
of the title compound in 1 mol·L
H
2
SO solution
4
Fig. 7. The cyclic voltammograms of title compound in 1 mol/L H
taining 2; 4; 8; 16 mmol H . Scan rate: 100 mV/s.
2
SO con-
4
−
1
as buffer solution at the scan rate 50 mV·s and are shown in Fig. 6. In
O
2 2
the potential range from +600 to −200 mV, there are three pairs of
Fig. 5. XPS of the title compound.
148

Y.-n. Zhang et al.
Inorganic Chemistry Communications 101 (2019) 145–149
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