Synthesis and antiviral activity of some (3,4-diaryl-3H-thiazol-2-ylidene) pyrimidin-2-yl amine derivatives

Article abstract of DOI:10.1080/10426507.2010.494643

Chemical Equation Presented Thirteen new (3,4-diaryl-3H-thiazol-2-ylidene) pyrimidin-2-yl amine derivatives were synthesized by reacting 1-aryl-3-pyrimidin-2-yl-thiourea derivatives and phenacyl bromides in absolute ethanol. The solid that separated was f

Full text of DOI:10.1080/10426507.2010.494643

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Synthesis and Antiviral Activity
of Some (3,4-Diaryl-3H-thiazol-2-
ylidene)pyrimidin-2-yl Amine Derivatives
a
Gülhan Turan-Zitouni a , Ahmet Özdemir a & Zafer Asım Kaplancıklı
a Faculty of Pharmacy, Department of Pharmaceutical Chemistry ,
Anadolu University , Eskişehir, Turkey
Published online: 19 Feb 2011.
To cite this article: Gülhan Turan-Zitouni , Ahmet Özdemir & Zafer Asım Kaplancıklı (2011)
Synthesis and Antiviral Activity of Some (3,4-Diaryl-3H-thiazol-2-ylidene)pyrimidin-2-yl Amine
Derivatives, Phosphorus, Sulfur, and Silicon and the Related Elements, 186:2, 233-239, DOI:
10.1080/10426507.2010.494643
To link to this article: http://dx.doi.org/10.1080/10426507.2010.494643
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Phosphorus, Sulfur, and Silicon, 186:233–239, 2011
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426507.2010.494643
SYNTHESIS AND ANTIVIRAL ACTIVITY OF SOME
(3,4-DIARYL-3H-THIAZOL-2-YLIDENE)PYRIMIDIN-2-YL
AMINE DERIVATIVES
¨
Gu¨lhan Turan-Zitouni, Ahmet Ozdemir,
and Zafer Asım Kaplancıklı
Faculty of Pharmacy, Department of Pharmaceutical Chemistry,
Anadolu University, Eskis¸ehir, Turkey
GRAPHICAL ABSTRACT
C2H5OH
N
S
N
C
S
+
N
R
R
1
1
N
N
H
N
H
N
NH2
1
N
Absolute
C2H5OH
S
N
N
R
3
Br
1
+
N
O
R
2
R1
R3
2a-m
R 2
Abstract Thirteen new (3,4-diaryl-3H-thiazol-2-ylidene)pyrimidin-2-yl amine derivatives
were synthesized by reacting 1-aryl-3-pyrimidin-2-yl-thiourea derivatives and phenacyl
bromides in absolute ethanol. The solid that separated was filtered and recrystallized from
ethanol. The structures of the synthesized compounds were confirmed by elemental analyses
and 1H NMR, 13C NMR, and EI-MS spectral data.
Supplemental materials are available for this article. Go to the publisher’s online edition of
Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
Keywords Antiviral activity; pyrimidine; thiazole
Received 9 March 2010; accepted 16 May 2010.
The antiviral evaluations were carried out by Dr. Michel Liuzzi (Idenix Senior Director Virology, Labora-
torio Cooperativo Idenix–Universita di Cagliari, Italy) and his team. Their contributions, as well as that of Dr.
Gilles Gosselin (CNRS Research Director, Senior Scientist Fellow, Idenix Montpellier, France), are gratefully
acknowledged.
Address correspondence to Gu¨lhan Turan-Zitouni, Faculty of Pharmacy, Department of Pharmaceutical
Chemistry, Anadolu University, Eskis¸ehir 26470, Turkey. E-mail: gturan@anadolu.edu.tr
233

234
G. TURAN-ZITOUNI ET AL.
INTRODUCTION
The development of nontoxic selective inhibitors of kinases and polymerases for
control of viral diseases has been the focus of intense research.1 Despite significant progress,
there is still a need for novel viral replication inhibitors, particularly for the treatment of
infection by human immunodeficiency virus (HIV), respiratory syncytial virus (RSV),
influenza virus (FLU), rhino virus (RV), and hepatitis C virus (HCV).
Molecules that possess sulfur atoms are common and very significant in living organ-
isms.2 One important class of heterocycle compound that contains one sulfur atom is known
as thiazole. This class is present in many natural and synthetic products with a wide range
of pharmacological activities, such as antiviral, anticancer, antibacterial, antifungal, anti-
convulsant, antiparkinsonian, and anti-inflammatory activities that can be well illustrated
by the large number of drugs in the market containing this function group.3,4 As examples,
the antiviral ritonavir, the antibacterial sulfathiazole, the vitamin B1, the antiparkinsonian
talipexole, the antischistosomal miridazole, the anthelmintic tiabendazole, the anti-ulcer
alizatidine, and the anticonvulsant riluzole can be cited.3,4 In the case of natural products,
thiazole is present as a subunit in a large number of terrestrial and marine compounds, with
different biological activities that represent a very important field in drug discovery.
On the other hand, the literature survey indicates that a large number of simple,
N-bridged, nitrogen- and sulfur-containing heterocyclic compounds carrying a pyrimidine
moiety are found to be associated with various biological activities. The chemistry of
pyrimidine and its derivatives has been studied for over a century due to their diverse
biological activities.5–8 They possess antiviral,9–16 antibacterial,17,18 anticancer,19,20 and
antihypertensive activities.21,22
Keeping in view these observations, we decided to undertake the synthesis of some
novel heterocycles containing the thiazole and pyrimidine moiety and to evaluate their
antiviral activity.
RESULTS AND DISCUSSION
In this study, 13 new compounds were synthesized. 1-Aryl-3-pyrimidin-2-
yl-thiourea derivatives (1) were prepared by reacting pyrimidin-2-yl amine with
p-substitutedpheny/benzyl isothiocyanate in accordance with the method described in the
literature.23 The reaction of 1-aryl-3-pyrimidin-2-yl-thiourea derivatives (1) and phenacyl
bromides gave the (3,4-diaryl-3H-thiazol-2-ylidene)pyrimidin-2-yl amine derivatves
(2a–m), as shown in Scheme 1. The formulas of compounds 2a–m were confirmed by
1H NMR, 13C NMR, and EI-MS spectral data. The antiviral activities of the synthesized
compounds were screened. The results showed that all of the tested compounds were
inactive against the test organism, as shown in Table S1 (Supplemental Materials, available
online).
Compounds 2a–m were tested for antiviral activity and cytotoxicity in various cell-
based assays.24
EXPERIMENTAL
Chemistry
All reagents were used as purchased from commercial suppliers without further
purification. Melting points were determined by using an Electrothermal 9100 digital

(3,4-DIARYL-3H-THIAZOL-2-YLIDENE)PYRIMIDIN-2-YL AMINES
235
C2H5OH
N
S
N
C
S
+
N
R
R
1
1
N
H
N
N
H
N
NH2
1
N
Absolute
C2H5OH
S
N
N
R
3
1
Br
+
N
O
R
2
R1
R3
2a-m
R 2
Scheme 1 The synthetic scheme for 2a–m.
melting point apparatus and were uncorrected. The compounds were checked for purity by
TLC on silica gel 60 F254. Spectroscopic data were recorded on the following instruments:
elemental analyses were performed on a Perkin Elmer EAL 240 elemental analyzer (Perkin
Elmer, Wellesly, MA, USA); 1H NMR and 13C NMR spectra of DMSO-d6 solutions (TMS as
internal standard) were respectively recorded at 400 and 100 MHz with a Bruker apparatus.
Splitting patterns are designated as follows: s, singlet; d, doublet; t, triplet; m, multiplet.
Chemical shift (δ) values are given in parts per million and coupling constants (J) in Hz.
GC-MS was performed with an Agilent Technologie 6890N GC apparatus (equipped with a
12 m × 0.20 mm dimethylpolysiloxane capillary column) linked to an Agilent 5973 EIMS
mass spectrometer.
General Procedure for Synthesis of the Compounds: Preparation of
1-Aryl-3-pyrimidin-2-yl-thiourea Derivatives (1)
A mixture of pyrimidin-2-yl amine (0.1 mol) and p-substitutedpheny/benzyl isothio-
cyanate (0.1 mol) in ethanol was refluxed for 2 h. The solid that separated upon cooling
was filtered, dried, and recrystallized from ethanol.
Preparation of (3,4-Diaryl-3H-thiazol-2-ylidene)pyrimidin-2-yl Amine
Derivatives (2a–m)
1-Aryl-3-pyrimidin-2-yl-thiourea derivatives (1) (0.001 mol) and the appropriate α-
bromoacetophenone (0.001 mol) in absolute ethanol were refluxed for 4–5 h. The solid
that separated was filtered and recrystallized from ethanol. Some characteristics of the
synthesized compounds are shown in Table 1.
[4-(4-Chlorophenyl)-3-phenyl-3H-thiazol-2-ylidene]pyrimidin-2-yl amine
1
(2a). H NMR (400 MHz, DMSO-d6, δ ppm): 7.01 (1H, t, J = 7.4 Hz), 7.22 (1H, t, J =
4.9 Hz), 7.35 (2H, t, J = 8.0 Hz), 7.44 (2H, d, J = 8.0 Hz), 7.67 (2H, d, J = 7.6 Hz),
7.72 (2H, d, J = 8.0 Hz), 8.63 (2H, d, J = 4.9 Hz), 10.60 (1H, s). 13C NMR (100 MHz,
DMSO-d6, δ ppm): 117.6 (2CH), 118.3 (CH), 120.9 (C), 122.1 (CH), 127.4 (2CH), 127.7
(CH), 129.1 (2CH), 131.5 (2CH), 132.8 (C), 134.5 (C), 140.5 (C), 157.1 (2CH), 160.2 (C),

236
G. TURAN-ZITOUNI ET AL.
Table 1 Characterization of the title compounds
Elemental Analyses
(Calc./Found.)
Yield
(%)
Mp
Mol. For.
(MW)
Compound
R1
R2
H
H
H
H
H
H
H
R3
Cl
(◦C)
C
H
N
2a
2b
2c
2d
2e
2f
Phenyl
59
64
61
58
65
53
52
67
59
63
65
61
67
216–218
173–174
205–207
274–275
127–128
202–204
241–243
C19H13ClN4S
364.86
C20H16N4S
344.44
C20H16N4OS
360.44
C20H15ClN4S
378.89
C20H15N5O2S
389.44
C21H18N4S
358.47
C21H18N4OS
374.47
62.55 3.59 15.36
63.10 3.23 14.87
69.74 4.68 16.27
69.96 5.36 16.38
66.65 4.47 15.54
66.85 4.20 15.64
63.40 3.99 14.79
63.73 4.59 15.11
61.68 3.88 17.98
61.86 4.38 18.12
70.36 5.06 15.63
70.81 5.53 15.94
67.36 4.85 14.96
67.78 4.72 15.17
Phenyl
CH3
OCH3
Cl
Phenyl
p-CH3-Phenyl
p-CH3-Phenyl
p-CH3-Phenyl
p-CH3-Phenyl
NO2
CH3
OCH3
Cl
2g
2h
2i
p-OCH3-Phenyl Cl
154–155 C20H14Cl2N4OS 55.95 3.29 13.05
429.33
C20H16N4S
344.44
C20H15ClN4S
378.89
C20H15N5O2S
389.44
C21H18N4S
358.47
56.24 3.28 13.54
69.74 4.68 16.27
69.97 4.97 16.41
63.40 3.99 14.79
63.76 4.07 14.93
61.68 3.88 17.98
61.76 4.58 18.11
70.36 5.06 15.63
70.69 5.18 15.83
58.12 3.41 13.55
58.37 3.44 13.52
CH2-Phenyl
CH2-Phenyl
CH2-Phenyl
CH2-Phenyl
CH2-Phenyl
H
H
H
H
Cl
H
169–171
242–243
193–194
168–170
213–214
2j
Cl
2k
2l
NO2
CH3
Cl
2m
C20H14Cl2N4S
413.33
163.4 (C). EI-MS (m/z): 366 (32), 365 (52), 364 (M+, 82%), 363 (100), 327 (2), 285 (6),
272 (6), 260 (6), 245 (11), 227 (6), 193 (5), 164 (16).
1
[4-(4-Tolyl)-3-phenyl-3H-thiazol-2-ylidene]pyrimidin-2-yl amine (2b). H
NMR (400 MHz, DMSO-d6, δ ppm): 2.36 (3H, s), 6.97–7.05 (2H, m), 7.16–7.23 (2H, m),
7.34 (2H, t, J = 8.0 Hz), 7.59 (2H, d, J = 8.0 Hz), 7.68 (2H, d, J = 8.0 Hz), 8.62 (2H, d,
J = 4.9 Hz), 10.59 (1H, s). 13C NMR (100 MHz, DMSO-d6, δ ppm): 20.9 (CH3), 117.5
(2CH), 118.2 (CH), 120.0 (C), 121.9 (CH), 128.0 (2CH), 129.0 (2CH), 129.6 (2CH), 132.9
(CH), 137.5 (C), 140.6 (C), 152.2 (C), 157.0 (2CH), 160.5 (C), 163.1 (C). EIMS (m/z): 344
(M+, 70%), 343 (100), 329 (1), 265 (2), 252 (4), 240 (5), 225 (11), 172 (9).
[4-(4-Methoxyphenyl)-3-phenyl-3H-thiazol-2-ylidene]pyrimidin-2-yl
1
amine (2c). H NMR (400 MHz, DMSO-d6, δ ppm): 3.82 (3H, s), 6.94 (1H, m), 6.96
(1H, m), 7.00 (1H, t, J = 7.4 Hz), 7.20 (1H, t, J = 4.9 Hz), 7.35 (2H, m), 7.67 (2H, m),
7.69 (2H, m), 8.63 (2H, d, J = 4.9 Hz), 10.54 (1H, s). 13C NMR (100 MHz, DMSO-d6, δ
ppm): 55.1 (CH3), 112.3 (2CH), 117.5 (2CH), 118.1 (CH), 119.4 (C), 121.9 (CH), 127.8
(CH), 129.0 (2CH), 131.1 (2CH), 140.6 (C), 152.0 (C), 157.0 (2CH), 159.3 (C), 160.6 (C),
163.0 (C). EI-MS (m/z): 360 (M+, 86%), 359 (100), 345 (16), 327 (1), 316 (6), 283 (2),
268 (3), 256 (2), 242 (4), 227 (6), 199 (6), 180 (9).

(3,4-DIARYL-3H-THIAZOL-2-YLIDENE)PYRIMIDIN-2-YL AMINES
237
[4-(4-Chlorophenyl)-3-(4-tolyl)-3H-thiazol-2-ylidene]pyrimidin-2-yl
1
amine (2d). H NMR (400 MHz, DMSO-d6, δ ppm): 2.28 (3H, s), 7.18 (2H, d, J = 7.8
Hz), 7.27 (1H, m), 7.56 (2H, d, J = 7.8 Hz), 7.98 (2H, d, J = 7.8 Hz), 8.27 (2H, d, J =
7.8 Hz), 8.67 (2H, d, J = 4.6 Hz), 10.61 (1H, s). 13C NMR (100 MHz, DMSO-d6, δ ppm):
20.98 (CH3), 99.98 (CH), 116.22 (2CH), 118.64 (CH), 122.35 (C), 127.15 (2CH), 129.54
(2CH), 131.17 (2CH), 133.09 (C), 137.798 (C), 142.277 (C), 145.98 (C), 148.98 (C),
157.26 (2CH), 163.80 (C). EI-MS (m/z): 378 (M+, 69%), 377 (100), 363 (4), 346 (27),
345 (15), 284 (9), 267 (7), 253 (2), 228 (6), 182 (11).
[4-(4-Nitrophenyl)-3-(4-tolyl)-3H-thiazol-2-ylidene]pyrimidin-2-yl amine
1
(2e). H NMR (400 MHz, DMSO-d6, δ ppm): 2.27 (3H, s), 7.16 (2H, d, J = 7.8 Hz), 7.25
(1H, m), 7.53 (2H, d, J = 7.8 Hz), 7.96 (2H, d, J = 7.8 Hz), 8.24 (2H, d, J = 7.8 Hz), 8.64
(2H, d, J = 4.6 Hz), 10.58 (1H, s). 13C NMR (100 MHz, DMSO-d6, δ ppm): 20.4 (CH3),
99.5 (CH), 117.9 (2CH), 118.6 (CH), 122.3 (C), 122.7 (2CH), 129.5 (2CH), 131.0 (2CH),
131.3 (C), 137.9 (C), 142.3 (C), 146.9 (C), 149.6 (C), 157.2 (2CH), 163.8 (C). EI-MS
(m/z): 390 (27), 389 (M+, 100%), 388 (58), 359 (6), 358 (7), 343 (8), 342 (18), 310 (7),
226 (15), 171 (16).
1
[3,4-Di-(4-tolyl)-3H-thiazol-2-ylidene]pyrimidin-2-yl amine (2f). H NMR
(400 MHz, DMSO-d6, δ ppm): 2.26 (3H, s), 2.36 (3H, s), 7.13–7.21 (5H, m), 7.50–7.60
(4H, m), 8.61 (2H, d, J = 4.9 Hz), 10.46 (1H, s). 13C NMR (100 MHz, DMSO-d6, δ
ppm): 20.38 (CH3), 20.95 (CH3), 117.74 (2CH), 118.04 (CH), 119.64 (C), 126.06 (CH),
127.96 (2CH), 129.44 (2CH), 129.56 (2CH), 130.97 (C), 132.87 (C), 137.51 (C), 152.24
(C), 156.98 (2CH), 160.55 (C), 163.41 (C). EI-MS (m/z): 358 (M+, 76%), 357 (100), 279
(3), 267 (2), 252 (4), 240 (5), 225 (11), 179 (6).
[4-(4-Methoxyphenyl-)3-(4-tolyl)-3H-thiazol-2-ylidene]pyrimidin-2-yl
1
amine (2g). H NMR (400 MHz, DMSO-d6, δ ppm): 2.29 (3H, s), 3.67 (3H, s),
7.14–7.23 (5H, m), 7.52–7.61 (4H, m), 8.63 (2H, d, J = 4.9 Hz), 10.53 (1H, s). 13C NMR
(100 MHz, DMSO-d6, δ ppm): 20.4 (CH3), 55.8 (CH3), 118.0 (2CH), 118.1 (CH), 119.7
(C), 126.2 (CH), 127.9 (2CH), 128.9 (2CH), 129.4 (2CH), 130.8 (C), 131.1 (C), 138.0 (C),
152.8 (C), 156.7 (2CH), 161.2 (C), 164.2 (C). EI-MS (m/z): 374 (M+, 72%), 358 (100),
277 (5), 253 (8), 240 (7), 223 (15), 180 (6).
[4-(3,4-Dichlorophenyl)-3-(4-methoxyphenyl)-3H-thiazol-2-ylidene]
1
pyrimidin-2-yl amine (2h). H NMR (400 MHz, DMSO-d6, δ ppm): 3.74 (3H, s), 6.94
(1H, m), 6.96 (1H, m), 7.21 (1H, t, J = 4.9 Hz), 7.53 (1H, m), 7.55 (1H, m), 7.63 (1H, d, J
= 8.4 Hz), 7.68 (1H, dd, J = 8.4, 1.9 Hz), 7.92 (1H, d, J = 1.9 Hz), 8.62 (2H, d, J = 4.9
Hz), 10.42 (1H, s). 13C NMR (100 MHz, DMSO-d6, δ ppm): 55.2 (CH3), 114.4 (2CH),
118.3 (CH), 120.0 (2CH), 120.9 (C), 129.6 (CH), 130.0 (CH), 130.1 (C), 130.6 (C), 131.5
(CH), 133.7 (CH), 136.3 (C), 149.4 (C), 154.9 (C), 157.1 (2CH), 160.0 (C), 164.4 (C).
EI-MS (m/z): 430 (M+, 71%), 428 (M+, 100%), 427 (28), 415 (34), 413 (49), 393 (2), 377
(2), 349 (3), 306 (2), 281 (8), 246 (14), 196 (16).
1
[4-Phenyl- 3-benzyl-3H-thiazol-2-ylidene]pyrimidin-2-yl amine (2i). H
NMR (400 MHz, DMSO-d6, δ ppm): 5.44 (2H, s), 6.90–7.70 (12H, m), 8.79 (2H, d, J =
5.0 Hz). 13C NMR (100 MHz, DMSO-d6, δ ppm): 49.1 (CH2), 107.4 (CH), 112.5 (CH),
125.5 (CH), 126.5 (2CH), 127.3 (CH), 128.3 (2CH), 128.6 (2CH), 129.3 (2CH), 129.5
(CH), 130.1 (C), 136.2 (C), 139.3 (C), 157.3 (CH), 157.4 (C), 164.6 (C). EI-MS (m/z): 344
(M+, 75%), 328 (2), 312 (25), 311 (100), 297 (1), 284 (1), 265 (19), 250 (11), 240 (6), 226
(5), 184 (16), 134 (32), 91 (48).
[4-(4-Chlorophenyl)-3-benzyl-3H-thiazol-2-ylidene]pyrimidin-2-yl amine
1
(2j). H NMR (400 MHz, DMSO-d6, δ ppm): 5.46 (2H, s), 6.88–7.27 (11H, m), 8.83

238
G. TURAN-ZITOUNI ET AL.
(2H, d, J = 5.1 Hz). 13C NMR (100 MHz, DMSO-d6, δ ppm): 49.4 (CH2), 107.9 (CH),
112.3 (CH), 125.4 (CH), 126.3 (2CH), 127.2 (CH), 128.4 (2CH), 129.0 (2CH), 129.5 (2CH),
129.9 (C), 130.0 (C), 136.3 (C), 139.2 (C), 157.5 (CH), 157.8 (C), 164.8 (C). EI-MS (m/z):
380 (23), 378 (M+, 62%), 362 (2), 347 (29), 346 (21), 345 (85), 299 (16), 284 (9), 252 (9),
184 (25), 182 (11), 168 (27), 91 (100).
[4-(4-Nitrophenyl)-3-benzyl-3H-thiazol-2-ylidene]pyrimidin-2-yl amine
1
(2k). H NMR (400 MHz, DMSO-d6, δ ppm): 5.47 (2H, s), 6.92–7.32 (11H, m), 8.82
(2H, d, J = 5.2 Hz). 13C NMR (100 MHz, DMSO-d6, δ ppm): 48.6 (CH2), 107.9 (CH),
113.5 (CH), 123.7 (2CH), 126.3 (2CH), 127.2 (CH), 128.5 (2CH), 130.3 (2CH), 136.5
(C), 136.7 (C), 137.1 (C), 147.6 (C), 157.5 (2CH), 162.4 (C), 163.5 (C). EI-MS (m/z): 390
(25), 389 (M+, 65%), 388 (55), 360 (5), 358 (7), 344 (8), 300 (15), 285 (10), 184 (26), 168
(25), 91 (100).
1
[4-(4-Tolyl)-3-benzyl-3H-thiazol-2-ylidene]pyrimidin-2-yl amine (2l). H
NMR (400 MHz, DMSO-d6, δ ppm): 2.35 (3H, s), 5.44 (2H, s), 6.90–7.30 (11H, m), 8.82
(2H, d, J = 5.1 Hz). 13C NMR (100 MHz, DMSO-d6, δ ppm): 20.9 (CH3), 49.2 (CH2),
107.74 (CH), 112.2 (CH), 125.4 (CH), 126.4 (2CH), 127.0 (C), 127.3 (CH), 128.2 (CH),
128.4 (2CH), 129.2 (2CH), 129.3 (CH), 136.1 (C), 139.3 (C), 139.6 (C), 157.3 (CH), 158.1
(C), 165.0 (C). EI-MS (m/z): 359 (18), 358 (M+, 68%), 357 (16), 326 (27), 325 (100), 279
(15), 267 (11), 252 (5), 240 (7), 184 (13), 162 (9), 147 (21), 91 (30).
[4-(3,4-Dichlorophenyl-)3-benzyl-3H-thiazol-2-ylidene]pyrimidin-2-yl
1
amine (2m). H NMR (400 MHz, DMSO-d6, δ ppm): 5.48 (2H, s), 6.91–7.32 (10H, m),
8.85 (2H, d, J = 5.1 Hz). 13C NMR (100 MHz, DMSO-d6, δ ppm): 47.8 (CH2), 107.5
(CH), 112.4 (CH), 124.0 (CH), 126.5 (2CH), 127.2 (CH), 128.2 (2CH), 130.0 (2CH),
130.4 (C), 136.4 (C), 137.0 (2C), 148.2 (C), 157.0 (2CH), 162.4 (C), 163.2 (C). EI-MS
(m/z): 413 (M+, 64%), 360 (2), 347 (29), 345 (22), 344 (87), 298 (19), 283 (7), 253 (8),
185 (25), 183 (12), 169 (28), 91 (100).
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