Synthesis, fluorescence properties and Zn2+ recognition of 4-Aryl-6-phenylpyrimidin-2(1H)-one

Article abstract of DOI:10.3184/030823408X389958

4-Aryl-6-phenylpyrimidin-2(1H)-ones were synthesised via a three-component one-pot cyclocondensation of aromatic aldehyde, acetophenone and urea catalysed by 0.2 ml (0.024 mol%) of concentration HCI in ionic liquid [BMIM][BF ₄]. The fluorescenc

Full text of DOI:10.3184/030823408X389958

JOURNAL OF CHEMICAL RESEARCH 2008
DECEMBER, 711-714
RESEARCH PAPER 711
Synthesis, fluorescence properties and Zn2+ recognition of
4-Aryl-6-phenylpyrimidin-2(1 H)-one
Hui WUa,b*, Xiu-mei Chena, Vu Wana,b, Ling Vec, Hai-qiang Xina, Hua-hong Xua, Li-ling Panga,
Rui Maa and Cai-hui Vuea
aSchool of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou, 221116, P.R. China
bKey Laboratory of Biotechnology on Medical Plant of Jiangsu Province, Xuzhou, 221116, P.R. China
Clnstitution of Environmental Monitoring of Siyang County, Jiangsu Province, Suqian, 223700, P.R. China
4-Aryl-6-phenylpyrimidin-2(1
H)-ones were synthesised via
a
three-component
one-pot cyclocondensation
of
aromatic aldehyde, acetophenone and urea catalysed by 0.2 ml (0.024 mol%) of concentration Hel in ionic liquid
[BMIM][BF4]. The fluorescence properties of product and partial products' efficient sensing of zinc ion were studied
in detail. The structure of 4,6-diphenylpyrimidin-2(1
H)-one was confirmed by X-ray analysis.
Keywords: 4-aryl-6-pheny1pyrimidin-2(1H)-ones, fluorescence properties, Zn2+recognition, ionic liquid, synthesis
Zinc is the second abundant transition metal in human body
only inferior to iron and plays an important role in various
biological processes. 1 Generally, the concentration of Zn2+
in the human body is different in various physiological
environments, and many other cations usually coexist with
Zn2+ in these environments. For example, the concentration
of intracellular Zn2+in serum is ca 12 !!M,2and that value in
the grey matter and brain tissue becomes ca 0.1-0.5 mM.3-4
Therefore, a sensitive and harmless technology to detect Zn2+
in living cells, especially in the presence of possible competing
cations, is very important. Because Zn2+ dose not give any
spectroscopic or magnetic signals due to its 3dlO4SO electronic
configuration, the detection of Zn2+ in biological systems
cannot be measured by the common analytical techniques such
as UV-Vis spectroscopy, Mossbauer spectroscopy, NMR and
EPR spectroscopy. Therefore, the fluorescence spectroscopy
is regarded as a good choice for the real-time and real-space
detection of Zn2+in living cells without damaging them.5
Pyrimidinone derivatives display various bio10gica16-7
and pharmaco10gica18-9 activities such as antiturnour action.
Experimentally, this skeleton can coordinate with metal ions
such as Zn2+, so it may be suitable for recognition of Zn2+.
Therefore, the synthesis of these heterocycle is interesting for
both organic synthesis and medical chemistry. There are only
few methods for the preparation of 4,6-diary1primidine-2(1H)-
ones. The same starting materials urea and chalcone have
been used by Sedova'slO and Fathalla's groupll to prepare 4,6-
diary1pyrimidin-2(1H)-ones in the presence ofHCl. However,
the two methods have some drawbacks such as harsh reaction
conditions and long reaction time (boiled for 7.5 h10 or
refluxed for 12 hll); use of toxic and volatile organic solvents;
use of excessive HC1 (5 m1), which equires an excessive base
as antiacid; low to moderate yields and low selectivity that
limit these methods to small-scale synthesis. Khosropour and
co-workers developed a three-component one-pot method to
synthesise these compounds under microwave irradiation, 12
with costly and unavailable catalysts (TCT(2,4,6-trichloro-
1,3,5-triazine)/Zn(OTt)2 or Bi(OTt)3)' Use of microwave
irradiation limits its industrialisation.
During the past two decades ionic liquids have gained
increasing attention for performing all types of reaction with
sometimes remarkable results. 13,14They have many properties
which make them of fundamental interest to all chemists.
Therefore, there are many good reasons to study ionic liquids
as alternative solvents in multi-component reaction. Here we
report a simple three-component one-pot cyclocondensation
of aromatic aldehyde, acetophenone and urea, catalysed by
0.024 mol% concentrated HCI in ionic liquid [BMlM][BF4],
to afford 4-aryl-6-phenyl pyrimidin-2(1H)-one 4 (Scheme 1),
the X-ray structure of compound 4a was determined and is
shown in Fig. 1. The results of further experiments indicated
that all products showed interesting fluorescent properties.
Moreover, products have electron-donating group in para
position (4b, 4c, 4d, 4k) provided an efficient fluorescence
response to Zn2
01
Fig. 1 X-ray structure of compound 4a.
Concentrated HCI
120°C [BMIM][BF41
2
3
Scheme
1
Synthesis of 4-aryl-6-phenylpyrimidin-2(1
H)-one.
* Correspondent. E-mail: wuhui72@yahoo.com.cn

712 JOURNAL OF CHEMICAL RESEARCH 2008
Table
Entry
1
Synthesis of 4-phenyl-6-phenylpyrimidin-2(1
H)-one under different conditionsa
Solvent
HCI
mol%
mol%
mol%
Yield/%
yield/%
yield/%
1
2
3
4
5
6
7
H20
EtOH
MeOH
[BMIM][BF4]
[BMIM][BF4]
[BMIM][BF4]
[BMIM][BF4]
0.024
0.024
0.024
0.012
0.024
0.048
0.060
0.024
0.024
0.024
0.012
0.024
0.048
0.060
0.024
0.024
0.024
0.012
0.024
0.048
0.060
10
15
20
15
50
95
85
70
aReaction conditions: benzaldehyde (2.0 mmol), acetophenone (2.0 mmol) and urea (4.0 mmol) at 120°C. bSilica sulfonic acid.
At the onset of this research, an effort was made to establish
the optimal conditions for the blank reaction of benzaldehyde,
acetophenone and urea, the results are summarised in Table 1.
Interestingly, this reaction showed an intriguing solvent
effect. Compared with classic organic solvent MeOH, EtOH
and H20, [BMIM] [BF4] (l-butyl-3-methylimidazolium
tetrafluoroborate) afforded the highest yield of the desired
product. [BMIM] [BF4] is not only a solvent but is also a
catalyst, so only a little amount of concentrated HCl was
needed as catalyst. The effect of different catalysts on yields
was also tested and the results indicated that the catalytic
activity of concentrated HCl was better than that of H2S04
and SSA (silica sulfonic acid). This may be due to the strong
electron withdrawing ability of chloride ion, which reduced
the density of the electron cloud around hydrogen ion.
So hydrogen ion could accept the electron more easily
enabling the reaction to proceed smoothly.
in Fig. 2, with the stepwise addition of Zn2+to a solution of
4d, the fluorescence emission at 429 nm gradually increases.
To explore the possible coordination mode of 4d with Zn2+,
some further experiments were performed when 4-aryl-6-
phenyl-pyrimidin-2(1H)-ones
without
electron-donating
groups in para position were used, the results showed no
appreciable fluorescence sensing abilities for Zn2+ under
the same conditions, which indicated steric and electronic
influence of substitutes. We then deduce that the possible
coordination mode of 4d with Zn2+ as shown in Scheme 2.
In addition, the Zn2+ sensing ability of 4d at different pH
values was also investigated (Fig. 3). The results show that 4d
exhibits poor sensing ability for Zn2+at a pH value below 5.8,
which may be due to the protonation of the N atom of 4d in
the acidic environment leading to a weak coordination ability
of Zn2+with 4d, but exhibited satisfactory Zn2+sensing ability
at a pH range of 7.4-10.6.
In order to examine the substrate scope of this reaction,
aromatic aldehydes with different substitutes were used under
the above-optimised reaction conditions (Scheme 1, Table 2).
From Table 2, all reactions proceeded smootWy to afforded
•••
J
RFI
the corresponding 4-aryl-6-phenylpyrimidin-2(lH)-ones
moderate to high yields.
in
3 ••
The fluorescence properties of products were shown in
Table 2 with notable fluorescence efficiency. From Table 2,
4d exhibits strong blue-violet fluorescence in EtOH with the
biggest fluorescence quantum yield (<1>p = 0.66, reference
to 9,1O-diphenylanthracence), which showed its potential
application as a fluorescent probe.
2 ••
,..
4d was chosen as sensor of Zn2+ because of its biggest
fluorescence quantum yield. The concentration of Zn2+ used
here is 2.0 x 10-5 mol·1-1, which is similar to the concentration
of intracellular Zn2+ in serum. It is noteworthy that this
sensing process can be readily distinguished by eyes. 4d was
colourless without Zn2+,but became yellow with the addition
of Zn2+.A quantitative study on the sensing ability of 4d for
Zn2+was performed by fluorescence titration. As can be seen
.5•
5••
55 •
•••
•••
•••
wav ••••• gth <nm)
Fig.2
Fluorescence spectral changes of 4d (3.4 x 10-5 M) upon
addition of Zn2+ ([Zn2+] = 1.0 x 10-5 M, 2.0
X
10-5 M, 3.4
10-5 M, 50
X
10-5 M,
10-5 M,
4.0
70
X 10-5 M, 7.0 X 10-5 M, 10 X 10-5 M, 20
10-5 M from k to a) in Tris-HCI buffer solution (pH = 7.40)
X
X
X
at 298.15 K.
Table
Entry
2
Synthesis and fluorescence properties of 4
M.p. (OC)
RFla
R,
Product
Time/h
Yield/%
<PFb
Aex/nm
Aem/nm
1
2
3
4
5
6
7
8
9
10
11
12
13
14
H
4-CI
4-CH3
4-0CH3
2-0CH3
4-0H
4a
4b
4c
4d
4e
4f
4g
4h
4i
3.5
5
5
5
5
5
5
5
5
5
5
5
5
95
80
95
80
80
95
80
90
80
81
79
70
70
75
227-228
239-228
>300
260
347
346
362
271
256
260
265
307
232
331
242
253
256
370
409
408
405
454
394
361
420
389
400
408
394
359
358
42
867
1162
882
49
20
36
307
99
42
0.10
0.45
0.50
0.66
0.10
0.09
0.10
0.16
0.13
0.14
0.21
0.11
0.08
0.09
244-245
219-220
264-265
267-268
278-278
242-242
242-243
228-229
228-229
>300
4-Br
4-CN
2,3-0CH3
3.4-0CH3
2.4-CI
3.4.5-0CH3
4-N02
2-CI
4j
4k
41
4m
4"
227
40
27
223-224
38
5
aRelative fluorescence intensity; bfluorescence quantum yield.

JOURNAL OF CHEMICAL RESEARCH 2008 713
Fig.4
Fluorescence responses of 4d to different metal ions in
Tris-Hel buffer solution (pH = 7.4). Ex = 362 nm, Em = 429 nm,
the concentration of 4d and all of metal ions is 3.4 x 10-5 M.
Scheme
2
Possible transition states.
28
26
24
22
20
18
structure determination for complex 4a was given by Smartapex
Broke diffractometer using SHELXS-97 (Sheldrick, 1990) for
structure solution and HELXL-97 (Sheldrick, 1997) for structure
refinement. Elemental analyses were performed on a Perkin-Elmer-
2400 elemental analyser. Fluorescence properties were reported on
F-4500 Fluorescence Spectrophotometer (Hitachi, Japan).
u:
D:: 16
General procedure for preparation of 4
A mixture of acetophenone (2.0 mmol), urea (4.0 mmol), aromatic
aldehyde (2.0 mmol) and 0.2 ml of concentrated HCl (36.5%,
0.24 mmol) was stirred in 0.5 mlof[BMIM][BF4] at 120°C for 3.5-5 h.
The reaction mixture was then quenched water and the products
were isolated by filtration followed by purification through simple
recystallisation with EtOH-DMF.
14
12
10
10
4-phenyl-6-phenylpyrimidin-2(IH)-one
(4a): IR (KBr, v, em-I):
pH
3321, 2905, 1654, 1603, 770; IH NMR (400 MHz, DMSO-~) 8:
8.17 (d, J= 7.2 Hz, 4H, ArH), 7.58-7.68 (m, 7H, ArH); BC NMR
(100 MHz, DMSO-d6) 8: 164.90, 157.00, 133.217, 132.29, 128.94,
128.05, 100.83, 56.03; Calcd for CI6H12N20: C, 77.40; H, 4.87; N,
11.28. Found: C, 77.20; H, 5.11; N, 11.19%. MS (ESI) [M + H] found
(expected): 249.1141 (249.1029).
Fig 3 Influence of pH on Zn2+ determination.
After validating the good Zn2+ sensing ability of 4d, the
sensing selectivity of 4d for Zn2+was also investigated through
a comparative study on the fluorescence responses of 4d to
different metal ions (AeJAem = 362 nm/405 nm). From Fig. 4,
4d shows significant response to Zn2+ among the metal ions
investigated, while its group 12 homologues, Cd2+,and Hg2+,
only exhibit slight fluorescence responses under the same
conditions. On the other hand, the fluorescence of 4d shows
no appreciable changes or slightly quenches with the addition
of Na+, Ca2+, Hg2+, Cu2+, Pb2+, Ba2+, Fe2+, Cd2+, Ag+ and
Cr3+ (the possible competing cations when Zn2+ sensors are
used in physiological studies). These results unambiguously
demonstrate the applicability of 4d as an efficient and special
sensor to Zn2+.
4-(4-Chlorophenyl)-6-phenylpyrimidin-2(IH)-one
(4b): IR (KBr,
v, em-I): 3410, 2894, 1644, 1492, 818, 774; IH NMR (400 MHz,
DMSO-~) 8: 12.04 (hr, s, lH, NH), 8.11-8.20 (m, 4H, ArH), 7.49-
7.60 (m, 6H, ArH); BC NMR (100 MHz, DMSO-d6) 8: 160.20,
144.93, 135.65, 129.Dl, 127.75, 109.64; Calcd for CI~llClN20: C,
67.97; H, 3.92; N, 9.91. Found: C, 68.20; H, 4.28; N, 9.60%. MS
(ESI) [M + H] found (expected): 283.0625 (283.0639).
6-Phenyl-4-p-tolylpyrimidin-2(IH)-one
(4c): IR (KBr, v, em-I):
3410,2794,1674,1592,848,773; IHNMR (400 MHz, DMSO-d6) 8:
8.11-8.20 (m, 4H, ArH), 7.49-7.60 (m, 6H, ArH), 2.36 (s, 3H, CH),
BC NMR (100 MHz, DMSO-d6) 8: 142.10, 131.90, 129.91, 129.28,
128.02, 128.00, 21.49; Calcd for C17HI~20: C, 77.84; H, 5.38; N,
10.68. Found: C, 77.03; H, 5.13; N, 10.77%. MS (ESI) [M + H]
found (expected): 263.1198 (263.1148).
4-(4-Methoxyphenyl)-6-phenylpyrimidin-2(IH)-one
(4d): IR (KBr,
In summary, 4-aryl-6-phenyl-pyrimidin-2(1H)-ones have
been synthesised from simple and available starting materials
in one pot. The fluorescence properties of products were
determined. The results indicated that products have electron-
donating group in para position which presents the obvious
fluorescence emission and can be readily monitored by both
eyes and fluorescence spectroscopy in the presence of Zn2+.
The fluorescence sensing to Zn2+of 4d was studied in detail
to develop a new efficient sensor to Zn2+.
v, em-I): 3320, 3096, 1615, 1513, 809, 744; IH NMR (400 MHz,
DMSO-~)8: 8.09 (tri, 2H,ArH), 7.99 (d,J=7.6 Hz,2H,ArH), 7.59
(d, J= 5.2 Hz, 3H, ArH), 7.39 (d,J= 8.0 Hz, 2H, ArH), 7.14 (m, lH,
ArH), 2.48 (s, 3H, CH); BC NMR (100 MHz, DMSO-d6) 8: 162.28,
131.56,129.56,128.98, 127.70, 117.40,55.66; Calcd forC17HI~202:
C, 73.37; H, 5.07; N, 10.07. Found: C, 73.15; H, 4.80; N, 10.00%.
MS (ESI) [M + H] found (expected): 279.1268 (279.1134).
4-(2-Methoxyphenyl)-6-phenylpyrimidin-2(IH)-one
(4e): IR (KBr,
v, em-I): 3320, 3096, 1615, 1513, 809, 744; IH NMR (400 MHz,
DMSO-~) 8: 8.19 (tri, 2H,ArH), 7.97 (d,J= 7.6, 2H,ArH), 7.56 (d,
J = 5.2 Hz, 3H, ArH), 7.39 (d, J = 8.0 Hz, 2H, ArH), 7.24(m, lH,
ArH), 2.58(s, 3H, CH); BC NMR (100 MHz, DMSO-d6) 8: 162.58,
137.60,129.66,127.98, 127.80, 117.90,55.56; Calcd forC17HI~202:
C, 73.37; H, 5.07; N, 10.07. Found: C, 73.44; H, 4.77; N, 10.48.
MS (ESI) [M + H] found (expected): 279.1185 (279.1134)%.
Experimental
All reagents were purchased from commercial sources and used
without further purification. TLC analysis was performed with glass
backed plates precoated with silica gel and examined under UV
(254 nm). NMR spectra were measured in DMSO-d6 with Me4Si
as the internal standards on a Broker advance DPX-400 at room
temperature. IR spectra were reported on Broker FTIR spectrometer,
absorbance is reported in em-I. Mass spectra was determined by using a
Broker MicrOTOF-QII high resolution mass spectrometer. The X-ray
4-(4-Hydroxyphenyl)-6-phenylpyrimidin-2(1H)-one
(41): IR (KBr,
v,em-I): 3331, 3300, 2928, 1659, 1616, 779; IH NMR (400 MHz,
DMSO-~) 8: 11.88 (hr, s, lH, NH), 10.21 (s, lH, OH), 8.08 (m,
4H, ArH), 7.56 (d, J= 7.2 Hz, 3H, ArH), 7.42 (s, lH, ArH), 6.91 (d,
J = 8.8 Hz, 2H, ArH); BC NMR (100 MHz, DMSO-d6) 8: 161.02,
131.50, 129.70, 128.96, 127,67, 115.77; Calcd for CI6H12N202: C,

714 JOURNAL OF CHEMICAL RESEARCH 2008
72.72; H, 4.58; N, 10.60. Found: C, 72.42; H, 4.58; N, 10.50%. MS
4-(2-Chlorophenyl)-6-phenylpyrimidin-2(1H)-one
(4n): IR (KEr,
(ESI) [M + Na] found (expected): 287.0773 (287.0796).
v, cm-I): 3320, 2849, 1623, 1458, 1349, 772, 690; IH NMR (400
MHz, DMSO-~) 12.04 (hr, s, lH, NH), 8.12-8.29 (m, 4H, ArH),
7.69-7.76 (m, 6H, ArH); BC NMR (100 MHz, DMSO-d6) 8: 156.97,
154.10, 149.20, 149.08, 146.51, 141.71, 138.68, 131.81, 129.07,
4-(4-Bromophenyl)-6-phenylpyrimidin-2(1H)-one
(4g): IR (KEr, v,
cm-I): 3401,2876,1698,754; IHNMR (400 MHz, DMSO-~) 8: 8.16
(d,J= 8.4 Hz, 4H,ArH), 7.77 (d,J= 8.4 Hz, 2H,ArH); 7.56-7.66 (m,
4H,ArH); BCNMR(100MHz,DMSO-~)8:
160.68,134.00,131.98,
127.77,123.21,117.15,69.19,53.86,49.93;
Ca1cd for CIJIllClN20:
131.69, 129.78, 129.02, 127.74, 125.43; Ca1cd for CIJIllBrN20:
C, 58.74; H, 3.39; N, 8.56. Found: C, 58.77; H, 3.69; N, 8.44%. MS
(ESI) [M + H] found (expected): 327.0096 (327.0134).
C, 67.97; H, 3.92; N, 9.91; Found: C, 68.20; H, 4.28; N, 9.60%; MS
(ESI) [M + H] found (expected): 283.0531 (283.0639).
4-(1,2-Dihydro-2-oxo-6-phenylpyrimidine-4-yl)benzonitrile
(4h):
Single crystal X-ray diffraction
IR (KEr, v, cm-I): 3420, 2894, 1620, 1680; IH NMR (400 MHz,
DMSO-~) 8: 12.22 (hr, s, lH, NH), 8.41 (d, J = 8.0 Hz, 2H, ArH),
8.19 (d,J= 6.4 Hz, 2H,ArH), 8.05 (d,J= 8.4 Hz, 2H,ArH), 7.59 (m,
4H,ArH); BCNMR (100 MHz,DMSO-d6) 8:159.70,132.91,129.06,
128.52,127.77,119.63,118.63,117.06,113.71,111.97;
C, 74.71; H, 4.06; N, 15.38. Found: C, 74.71; H, 4.29; N, 15.06%.
The single crystal growth was carried out in EtOH at room temperature.
Crystal data for 4a: empirical formula: CIJI 12N20,colourless, crystal
dimension: 0.32 x 0.19 x 0.16 mm, monoclinic, space group: P2(1)/
c, a
=
13.2000(2) A, b = 7.3243(14) A, c = 13.774(2) A, a = 90",
C17HllN302:
~
=
108.162°, Y = 90°, V = 1265.3(4) A-3, Mr 248.28, Z 4,
=
=
MS (ESI) [M + H] found (expected): 274.0989 (274.0981).
Dc = 1.303 Mg/m-3, A. = 0.71073 A, ,u(Mo Ka) = 0.083 mm-I, F(OOO)
= 520, S = 1.012, RI = 0.0459, WR2= 0.0921, the number of reflections
collected and the number of unique reflections is 6310 and 2234
respectively. Crystallographic data for the structure of 4a reported have
been deposited with the Cambridge Crystallographic Data Centre as
supplementary publication No. CCDC-649143.
4-(2, 3-Dimethoxyphenyl)-6-phenylpyrimidin-2
(1H)-one (41): IR
(KEr, v, cm-I): 3389, 2935, 1662, 1535, 1128, 868, 770; IH NMR
(400 MHz, DMSO-~) 8: 8.00 (d, J = 6.8 Hz, 2H, ArH), 7.75 (d,
J = 5.6 Hz, lH, ArH), 7.56 (m, 4H, ArH), 7.09 (d, J = 8.0 Hz, lH,
ArH), 6.83 (t, lH, ArH), 3.77 (s, 3H, OCH3), 2.46 (s, 3H, OCH3);
BC NMR (100 MHz, DMSO-d6) 8: 149.12, 132.07, 129.12, 127.99,
120.61, 118.03, 115.95, 56.00, 55.97; Ca1cd for CI8HI~203: C,
70.12; H, 5.23; N, 9.09. Found: C, 70.01; H, 5.08; N, 8.89%. MS
(ESI) [M + H] found (expected): 309.1185 (309.1239).
We are grateful to the foundation of the National
Natural Sciences Foundation of China (No. 20772103),
"Natural Sciences Foundation of Jiangsu Province" (No.
BK2007028), and the Surpassing Project in Jiangsu Province
(No.QL200607) for financial support.
4-(3,4-Dimethoxyphenyl)-6-phenylpyrimidin-2(1H)-one
(4j): IR (KEr,
v, em-I):3200, 2835, 1575, 1169, 838, 762; IH NMR (400 MHz,
DMSO-~) 8: 11.95 (hr, s, lH, NH), 8.15 (d, J = 6.4 Hz, 2H, ArH),
7.82 (d,J= 8.4 Hz, lH,ArH), 7.73 (s, lH,ArH), 7.57 (m,4H,ArH),
7.12 (d, J = 8.4 Hz, lH, ArH), 3.88 (d, 6H, OCH3); BC NMR (100
MHz, DMSO-d6) 8: 145.02, 136.07, 128.12, 126.99, 121.61, 117.03,
116.95, 57.00, 55.96; Ca1cd for CI8HI~203: C, 70.12; H, 5.23; N,
9.09. Found: C, 70.01; H, 5.08; N, 8.89%. MS (ESI) [M + H] found
(expected): 309.1338 (309.1240).
Received 15 September 2008; accepted 30 October 2008
Paper 08/0168 doi: 10.3184/030823408X389958
Published online: 12 December 2008
4-(2,4-Dichlorophenyl)-6-phenylpyrimidin-2(1H)-one
(4k): IR (KEr,
References
v, em-I): 3420, 2899, 1634, 1498, 828, 778; IH NMR (400 MHz,
DMSO-d6) 8: 12.04 (hr, s, lH, NH), 8.11-8.20 (m, 4H, ArH), 7.49-7.60
(m, 5H, ArH); BC NMR (100 MHz, DMSO-~) 8: 160.20, 144.93,
135.65,132.00, 129.00, 127.05, 117,26; Calcd for CIJIIOC12N20: C,
60.59; H, 3.18; N, 8.83; Found: C, 60.45; H, 3.15; N, 8.59%. MS (ESI)
[M +H] found (expected): 317.0515 (317.0249).
1
2
3
P.-J. Jiang and Z.-J. Guo, Coord. Chem. Rev., 2004, 248, 205.
M.M. Paker, F.L. Humaller and D. Mahler, J. Clin. Chem., 1967, 13, 353.
M.A. Lovell, J.D. Robertson, w.J. Teesdale, J.L. Campbell and
W.R. Markesbery,J. Neurol. Sci., 1998, 158,47.
4
5
A.I. Bush, Curr. Opin. Chem. Boil., 2000, 4,184.
J. Zhang, R.E. Campbell, A.Y. Ting and R.Y. Tsien, Nat. Rev. Mol. Cell
Bioi., 2002, 3, 906.
4-(3,4,5- Trimethoxyphenyl)-6-phenylpyrimidin-2(1
H)-one (41): IR
(KEr, v, em-I): 3283,2840, 1634, 1535, 1128, 868, 770; IH NMR
(400 MHz, DMSO-d6) 8: 12.00 (hr, s, lH, NH), 8.12 (d, J= 6.0 Hz,
2H, ArH), 7.53 (m, 6H, ArH), 3.88 (d, 9H, OCH3); BC NMR
(100 MHz, DMSO-d6) 8: 153.27, 140.66, 131.70, 128.97, 127.99,
105.39, 60.36, 56.44; Calcd for CI~18N204: C, 67.44; H, 5.36; N,
8.28. Found: C, 67.41; H, 5.17; N, 8.27%; MS (ESI) [M + H] found
(expected): 339.1448 (339.1345).
6
B. Lagu, D. Tian, G. Chin, D. Nagarathrarn, J. Fang, Q. Shoo, C. Forray,
R.W. Ransom, R.S. L. Chang, K.P. Vyas, K. Zhang and C. Gluchowski,
Bioorg. Med. Chem. Lett., 2000, 10, 175.
7
8
9
A.K. Sharma, S. Jayakumar, M.S. Hundal and M.P. Mahajan, J. Chem.
Soc., Perkin Trans.I, 2002,774.
S. Sasaki, N. Cho, Y. Nara, M. Harada, S. Endo, N. Suzuki, S. Furuya and
M. Fujinor,J. Med.Chem., 2003, 46,113.
S. Bartolini, A. Mai, M. Artico, N. Paesano, D. Rotili, C. Spadafora and
G. Sbardella,J. Med.Chem., 2005, 48, 6776.
4-(4-Nitrophenyl)-6-phenylpyrimidin-2(1H)-one
(4m): IR (KEr, v,
cm-I): 3418,2918, 1681, 1560, 1351,858,758; IH NMR (400 MHz,
DMSO-~) 8: 8.49 (d, J = 8.4 Hz, lH, ArH), 8.39 (d, J = 8.8 Hz,
2H, ArH), 8.20 (d, J = 5.2 Hz, lH, ArH), 7.99 (d, J = 8.4 Hz, lH,
ArH), 7.59 (d,J= 7.2 Hz, 2H,ArH), 7.29 (d,J= 8.4 Hz, lH,ArH),
7.17 (s, lH, ArH), 6.95 (d, J = 9.2 Hz, lH, ArH); BC NMR (100
MHz, DMSO-d6) 8:155.86, 154.02, 143.88, 137.83, 134.53, 131.15,
129.33, 128.80, 128.63, 128.51, 126.76, 126.72, 126.65, 71.11,
50.11; Calcd for C16HllN303: C, 65.53; H, 3.78; N, 14.33. Found:
C, 65.85; H, 3.54; N, 14.40%. MS (ESI) [M + H] found (expected):
294.0828(294.0879).
10 V.F. Sedova and O.P. Shkurko, Chemistry of Heterocyclic Compounds,
2004, 40, 194.
11 S. Fatha11a, M. Award and M.S. Mohamed, Archives of Pharmacal
Research, 2005, 28, 1205.
12 A.R. Khosropour, I. Mohammadpoor-Ba1tork, M.M. Khodaei and
M. Jokar, Heterocycles, 2006, 68,1551.
13 F.-A. Kang, J. Kodah, O. Guan, X. Li and W.V. Murray, J. Org. Chem.,
2005,70,1957.
14 X.-F. Yang, M. Wang, R.S. Varma and C.-J. Li, Org. Lett., 2003, 5, 657.