Thio analogs of pyrimidine bases: Synthesis and spectroscopic study of new potentially biologically active disulfides of N,O-(N,N- or O,O-)-Di- and N,N,O-Tri-(o-, m-, and p-)bromobenzyl-2-thiouracils

Article abstract of DOI:10.1080/10426500903501470

Nine new disulfides of N,O-(N,N- or O,O-)-di- and N,N,O-tri-(o-, m- and p-)bromobenzyl-2-thiouracils have been prepared. The structures of these compounds were confirmed by spectroscopic (FT-IR, UV-Vis, 1H NMR) and elemental analyses. Estimation of pharma

Full text of DOI:10.1080/10426500903501470

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Phosphorus, Sulfur, and Silicon and the
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Thio Analogs of Pyrimidine Bases:
Synthesis And Spectroscopic Study of
New Potentially Biologically Active
Disulfides of N,O-(N,N- or O,O-)-Di- and
N,N,O-Tri-(o-, m-, and p-)bromobenzyl-2-
thiouracils
Tomasz Pospieszny a & Elżbieta Wyrzykiewicz a
a Faculty of Chemistry , Adam Mickiewicz University , Poznan,
Poland
Published online: 24 Sep 2010.
To cite this article: Tomasz Pospieszny & Elżbieta Wyrzykiewicz (2010) Thio Analogs of Pyrimidine
Bases: Synthesis And Spectroscopic Study of New Potentially Biologically Active Disulfides of N,O-(N,N-
or O,O-)-Di- and N,N,O-Tri-(o-, m-, and p-)bromobenzyl-2-thiouracils, Phosphorus, Sulfur, and Silicon
and the Related Elements, 185:10, 2101-2107, DOI: 10.1080/10426500903501470
To link to this article: http://dx.doi.org/10.1080/10426500903501470
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Phosphorus, Sulfur, and Silicon, 185:2101–2107, 2010
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500903501470
THIO ANALOGS OF PYRIMIDINE BASES: SYNTHESIS
AND SPECTROSCOPIC STUDY OF NEW POTENTIALLY
BIOLOGICALLY ACTIVE DISULFIDES OF N,O-(N,N- OR
O,O-)-DI- AND N,N,O-TRI-(o-, m-, AND
p-)BROMOBENZYL-2-THIOURACILS
Tomasz Pospieszny and Elz˙bieta Wyrzykiewicz
Faculty of Chemistry, Adam Mickiewicz University, Poznan, Poland
Nine new disulfides of N,O-(N,N- or O,O-)-di- and N,N,O-tri-(o-, m- and p-)bromobenzyl-
2-thiouracils have been prepared. The structures of these compounds were confirmed by
spectroscopic (FT-IR, UV-Vis, 1H NMR) and elemental analyses. Estimation of pharma-
cotherapeutic potential has been made for synthesized compounds on the basis of Prediction
of Activity Spectra for Substances (PASS).
Keywords FT-IR; 1H NMR; o-(m- and p-)bromobenzyl bromides; Prediction of Activity
Spectra for Substances (PASS); structural isomers; 2-thiouracils (2-TU); UV-Vis
INTRODUCTION
The variety of organosulfur compounds that contain disulfide bonds have been re-
ported to be effective in cardiovascular diseases, because of their hypocholesterolemic,
hypolipidemic, antihypertensive, antidiabetic, antithrombotic, and antihyperhomocysteine-
mia effects, and to possess many others biological activities including antimicriolisial,
antioxidant, anticancerogenic, antimutagenic, antiasthmatic, immunomodulatory, and pre-
biotic activities.1–6
Recently, we have reported the syntheses, physicochemical properties, and results of
1
a spectroscopic (FT-IR, UV/Vis, H NMR) study of 2,4-di-o-(m- and p-)bromo-(chloro-
and nitro-)benzylthio-5-bromouracils (and 6-methyluracils).7 However, to the best of our
knowledge, no work has been published on the synthesis and physicochemical proper-
ties of disulfides derivatives of N,O-(N,N- or O,O-)-di- and N,N,O-tri-(o-, m-, and p-
)bromobenzyl-2-thiouracils. The novel pharmacological actions of these compounds have
been found on the basis of a computer-aided drug discovery approach with the compounds
program Prediction of Activity Spectra for Substances (PASS).8–12 It is based on a robust
analysis of structure–activity relationships in a heterogeneous training set currently includ-
ing about 60,000 biologically active compounds from different chemical series with about
4500 types of biological activity. Since only the structural formula of the chemical com-
pound is necessary to obtain a PASS prediction, this approach can be used at the earliest
Received 26 August 2009; accepted 19 November 2009.
Address correspondence to Tomasz Pospieszny, Faculty of Chemistry, Adam Mickiewicz University,
Grunwaldzka 6, 60-780, Poznan, Poland. E-mail: tposp@amu.edu.pl
2101

2102
T. POSPIESZNY AND E. WYRZYKIEWICZ
O
N
O
4
H
S
5
6
N3
3
A
A
2
S
N
O
S
N
O
2
N
S
N
Br
4
5
B
1
B
H
N
N
1
6
Br
Br
1. o-Br
2. m-Br
3. p-Br
4
Br
Br
O
Br
O
N
N
A
A
S
N
O
S
N
O
N
S
N
S
B
B
N
N
Br
Br
Br
6
5
O
N
A
S
N
O
N
S
B
H
N
Br
Br
7. o-Br
8. m-Br
9. p-Br
Figure 1 Structures and numbers of atoms of disulfides of N,O-(N,N- or O,O-)-di- (1–6) and N,N,O-tri-(o-, m-,
and p-)bromobenzyl-2-thiouracils (7–9).
stage of investigation. There are many examples of successful uses of the PASS approach
that have led to new pharmacological agents.
The analysis of PASS prediction results of bis[uracils] disulfide and bis[6-
methyluracil] disulfide have prompted us to synthesize a series of new disulfide
derivatives of N1(B),O(B)-di-o-(m- and p-)bromobenzyl-2-thiouracils (1–3), N1(A),N1(B)
-
di-p-bromobenzyl-2-thiouracil (4), O(A),O(B)-di-m-bromobenzyl-2-thiouracil (5), and
N1(A),O(B)-di-o-bromobenzyl-2-thiouracil (6), as well as new disulfides derivatives of
N1(A),N1(B),O(B)-tri-o-(m- and p-) bromobenzyl-2-thiouracils (7–9) (Figure 1).
This article deals with the synthesis and physicochemical properties of 1–9. Addi-
tionally the analyses of biological activity spectra prediction for 1–9 made in this article
are good examples of in silico studies of chemical compounds.
RESULTS AND DISCUSSION
A series of new disulfides of N1(B),O(B)-di-o-(m- and p-)bromobenzyl-2-thiouracils
(1–3), N1(A),N1(B)-di-p-bromobenzyl-2-thiouracil (4), O(A),O(B)-di-m-bromobenzyl-2-
thiouracil (5), N1(A),O(B)-di-o-bromobenzyl-2-thiouracil (6), and N1(A),N1(B),O(B)-tri-o-(m-

THIO ANALOGS OF PYRIMIDINE BASES
2103
and p-)bromo- benzyl-2-thiouracils (7–9) (Figure 1) were made by oxidation and subse-
quent benzylation of 2-thiouracil. Treatment of 2-thiouracil with o-(m- and p-)bromobenzyl
bromides and K2CO3 in boiling DMF gave 1–9.
The reaction of 2-thiouracil with two-fold molar excess of o-(m- and p-)bromobenzyl
bromide in boiling DMF in the presence of 1.50 equivalent of K2CO3 lead to 1 and 6, 2
and 5, and 3 and 4, respectively. The preparation of 1–6 was probably promoted by prior
conversions of 2-thiouracil into their respective disulfides with a bromide oxidizing agent.
It is well known in the literature that such oxidative S S coupling occurs in the presence of
halogens.13 The oxidation of thiols to disulfides by means of bromine/aqueous potassium
hydrogen carbonate in two-phase system has also been described.14,15 The competition in the
further reaction with benzylic cation is between N1- and O-. The reactions of benzylations
are largely governed by the same nature of the benzylation agents, i.e., soft electrophiles
(in some respect soft acids) o- (m- and p-)bromobenzyl bromides. The differences in the
reactivity of these bromobenzyl bromides gave N1(B), O(B) (or N1(A), O(A)) together with
N1(A), N1(B) (O(A), O(B) or N1(B), O(A)) benzyl disubstitution of the uracil ring. The pairs of
isomers 1 and 6 (2 and 5 or 3 and 4) were obtained by these dibenzylations.
The reactions of 2-thiouracil with threefold molar excess of o-(m- and p-)bromobenzyl
bromide in boiling DMF in the presence of 1.50 equivalent of K2CO3 led to disulfides of
N1(A),N1(B),O(B)-tri-o-(m- and p-)bromobenzyl-2-thiouracils (7–9).
The structures of disulfides 1–9 were confirmed by examination of their UV/Vis,
FT-IR, and 1H NMR spectra (Table I), as well as elemental analyses (Table II).
The 1H NMR data of 1–9 are given in Table I. Assignments of the 1H NMR resonances
of these compounds were deduced on the basis of their signal multiplicities and by the
1
1
corrected application of two-dimensional NMR technique H-1H COSY. The H NMR
spectra of 1–3 and 6 reveal singlets of 2H of N-CH2 at 5.46 ppm, as well as a singlet of 2H
of O CH2 at 4.48 ppm. The 1H NMR spectrum of 4 reveals a singlet of 4H of N CH2 at
5.39 ppm, and the 1H NMR spectrum of 5 reveals a singlet of O CH2 at 4.39 ppm.
In the 1H NMR spectra of 7–9 singlets of 2H of N CH2 (in the ring A) are situated
at 4.91, 5.21, and 5.17 ppm, respectively, and singlets of 2H of N CH2 (in the ring B) at
5.41, 5.42, and 5.40 ppm, respectively. The 1H NMR spectra of 7–9 reveal singlets of 2H
of O CH2 (in the ring B) at 4.48, 4.45, and 4.42, respectively. Singlets of C2 H of ring B
in the 1H NMR spectra of 1–3 and 7–9 are seen at the range 2.50–2.52 ppm (Table I).
The FT-IR spectra of 1–4 and 6–9 show ν C4 O absorption bands in the region
1671–1716 cm−1 (Table I). The absorption bands of ν N CH2 vibrations of 1–4 and 6–9
are seen in IR spectra in the region 2780–2929 cm−1. The absorption bands of ν O CH2
vibration of 1–3 and 5–9 are seen in the IR spectra in the region 1250–1277 cm−1. The
UV/Vis spectra of 1–6 show λmax in the range 282–296 nm. The UV/Vis spectra of 7–9
show λmax in the range 271 and 295–297 nm, respectively (Table I).
In this article, the biological activity spectra were predicted for all nine synthesized
compounds (1–9) with PASS. We have also selected the types of activity that were predicted
for a potential compound with the highest probability (focal activities). They are presented
in Table III. According to these data, the most frequently predicted types of biological ac-
tivity are prolylaminopeptidase inhibitor, aryloalkylacylamidase inhibitor, mannotetraose-
2-alpha-N-acetylglucosaminyltransferase inhibitor, and N-acetyllactosamine synthase in-
hibitor. In ought to be pointed out that in the series of disulfides with o-bromobenzyl
substituent (1, 6, 7), such activities as antiviral (poxvirus) and interleukin antagonist have
been predicted.

2104
T. POSPIESZNY AND E. WYRZYKIEWICZ
Table I FT-IR, UV-Vis, and 1H NMR data of compounds 1–9
1H NMR (DMSOd6) ppm
FT-IR cm−1 (KBr)
C5-H(d)A
C5-H(d)B
C6-H(d)A
C6-H(d)B
N1CH2(s)A
N1CH2(s)B
O-CH2(s)
C2-H(s)B
UV/Vis (CH3OH)
νC4
O
νN CH2
νO CH2
Compo
λmax nm (log ε)
νC5 C6
phenyl(m)
1
240.0
(4.42)
292.0
(4.13)
1698
1540
2864
1275
6.14 J = 7 Hz
6.77 J = 7 Hz
7.94 J = 7 Hz
8.43 J = 7 Hz
6.14 J = 7 Hz
6.77 J = 7 Hz
7.94 J = 7 Hz
8.43 J = 7 Hz
6.14 J = 7 Hz
6.76 J = 7 Hz
7.94 J = 7 Hz
8.38 J = 7 Hz
6.09 J = 7 Hz
6.09 J = 7 Hz
7.93 J = 7 Hz
7.93 J = 7 Hz
7.27 J = 7 Hz
7.27 J = 7 Hz
7.49 J = 7 Hz
7.49 J = 7 Hz
6.10 J = 7 Hz
7.27 J = 7 Hz
7.86 J = 7 Hz
7.49 J = 7 Hz
6.15 J = 7 Hz
7.25 J = 7 Hz
7.93 J = 7 Hz
8.42 J = 7 Hz
6.32 J = 7 Hz
7.16 J = 7 Hz
7.93 J = 7 Hz
8.40 J = 7 Hz
6.22 J = 7 Hz
7.17 J = 7 Hz
7.93 J = 7 Hz
8.13 J = 7 Hz
5.46 (2H)
—
4.48 (2H)
2.52 (1H)
5.41 (2H)
—
4.45 (2H)
2.51 (1H)
5.39 (2H)
—
4.37 (2H)
2.52 (1H)
5.39 (4H)
—
7.13–7.59
2
3
4
5
6
7
8
9
240.0
(4.49)
292.0
(4.23)
1714
1494
2846
1250
7.25–7.80
7.21–7.90
7.21–7.69
7.20–7.70
7.18–7.67
7.13–7.59
7.18–7.67
7.21–7.61
239.0
(4.49)
292.0
(4.17)
1684
1539
2857
1276
228.0
(4.49)
272.0
(4.41)
1719
1492
2929
—
—
—
—
—
223.0
(4.46)
287.5
(4.19)
—
1592
—
1270
4.39 (4H)
—
5.40 (2H)
—
4.48 (2H)
—
4.91 (2H)
5.21 (2H)
4.48 (2H)
2.51 (1H)
5.21 (2H)
5.42 (2H)
4.45 (2H)
2.50 (1H)
5.17 (2H)
5.40 (2H)
4.42 (2H)
2.50 (1H)
225.0
(4.47)
290.0
(4.27)
1671
1497
2820
1260
239.5
(4.16)
271.5
(4.34)
295.0
(4.33)
1673
1594
2823
1270
239.0
(4.08)
271.5
(4.25)
296.5
(4.18)
1713
1569
2780
1277
240.5
(4.35)
271.0
(4.28)
297.5
(4.23)
1716
1542
2781
1230
EXPERIMENTAL
The purity of all described compounds was checked by melting points, TLC, and ele-
mental analyses. Melting points (uncorrected) were determined on a Bo˝etius microscope hot
stage. Rf values refer to silica gel F254 TLC plates (Merck) developed with CHCl3:CH3OH
(40:1) (1–6) and CHCl3:CH3OH (10:1) (7–9; Table II). UV/Vis spectra were recorded with
a Specord UV/Vis Spectrophotometer in CHCl3. IR spectra were recorded with a FT-IR
Bruker IFS-113 Spectrophotometer in KBr pellets. The 1H NMR spectra were determined
with Varian Gemini 300 (300 MHz) spectrometer in CDCl3 solution at a concentration

THIO ANALOGS OF PYRIMIDINE BASES
2105
Table II Physical and analytical data of compounds 1–6 and 7–9
Analysis
Calculated
H
Found
H
Yield
(%)
Mp
(◦C)
Rf
TLC
Compound
Formula MW
C
N
C
N
1
2
3
4
5
6
7
8
9
C22H18N4S2O2Br2
594.34
C22H18N4S2O2Br2
594.34
C22H18N4S2O2Br2
594.34
C22H16N4S2O2Br2
592.32
56
53
58
20
18
19
23
28
36
150–151 0.47∗
140–141 0.46∗
162–163 0.45∗
201–203 0.51∗
140–141 0.52∗
180–181 0.50∗
44.44 3.03 9.42 44.15 3.00
44.44 3.03 9.42 44.27 3.06
44.44 3.03 9.42 44.28 3.21
44.59 2.70 9.45 44.62 2.80
44.59 2.70 9.45 44.70 2.58
44.59 2.70 9.45 44.80 2.48
9.40
9.53
9.20
9.60
9.65
9.62
7.46
7.50
7.64
C22H16N4S2O2Br2
592.32
C
22H16N4S2O2Br2
592.32
C29H24N4S2O2Br3
763.36
C29H24N4S2O2Br3
763.36
C29H24N4S2O2Br3
763.36
170–173 0.63∗∗ 45.66 2.88 7.34 45.40 2.98
150–153 0.83∗∗ 45.66 2.88 7.34 45.32 2.80
140–143 0.93∗∗ 45.66 2.88 7.34 45.50 3.02
∗CHCl3:CH3OH (40:1).
∗∗CHCl3:CH3OH (10:1).
between 0.25 and 0.40 M in the 5 mm sample tubes at ambient temperature. Chemical
shifts are given in δ scale (ppm). Elemental analyses were performed with a Vector Euro
EA 3000 analyzer.
The Synthesis of Disulfides 1–9
To a solution of 2-thiouracil (0.5 g, 3.90 mmol) in DMF (25 mL), K2CO3 (0.6 g, 6
mmol) was added. The reaction mixture was heated to reflux for 20 min until the K2CO3
was completely dissolved. To this mixture, 1.95 g (7.8 mmol) 1–6 or 3 g (12 mmol) 7–9 of
o-(m- or p-)bromobenzyl bromide was added, respectively. After 3 h of boiling, the solvent
was filtered and acidified with dil. HCl (HCl:H2O, 1:1). Then the precipitated solid was
collected by filtration and dissolved in 10 mL of DMF, and was applied on a silica gel col-
umn (15 g of silica gel 60-Merck; the parameters of column: length 27 cm, ꢀ 1.8 cm). The
column was eluted successively with the following mixtures of solvents: CH2Cl2 (100 mL),
CH2Cl2:CH3OH (90:1; 100 mL), CH2Cl2:CH3OH (80:1; 100 mL), CH2Cl2:CH3OH (70:1;
100 mL), CH2Cl2:CH3OH (60:1; 100 mL), CH2Cl2:CH3OH (50:1; 100 mL). The fractions
of 100 mL were collected, respectively. On the basis of analytical TLC, fractions of de-
rived product were obtained (fraction 5: compound 1; fraction 6: compound 2; fraction 7:
compound 3; fraction 8: compounds 6 and 7; fraction 9: compounds 5 and 8; fraction 10:
compounds 4 and 9). They were dried on a rotary evaporator. Compounds 1–9 were shown
to be analytically pure without need for any further purification (Tables I and II).

2106
T. POSPIESZNY AND E. WYRZYKIEWICZ
Table III Predicted activity (PA) values for predicted biological activity of compounds 1–9
Compound
1
Focal predicted activity (PA > 0.5)
2,6-Dihydroxypyridine-3-monooxygenase inhibitor (0.843)
Antiviral (Poxvirus) (0.642)
Prolyl aminopeptidase inhibitor (0.677)
Interleukin antagonist (0.565)
N-Acetyllactosamine synthase inhibitor (0.564)
Mannotetraose 2-aplha-N-acetylglucosaminyltransferase inhibitor (0.572)
Aryloalkyl acylamidase inhibitor (0.546)
2
3
4
2,6-Dihydroxypyridine-3-monooxygenase inhibitor (0.836)
Prolyl aminopeptidase inhibitor (0.785)
N-Acetyllactosamine synthase inhibitor (0.589)
Mannotetraose 2-aplha-N-acetylglucosaminyltransferase inhibitor (0.555)
Aryloalkyl acylamidase inhibitor (0.526)
2,6-Dihydroxypyridine-3-monooxygenase inhibitor (0.841)
Prolyl aminopeptidase inhibitor (0.792)
Mannotetraose 2-aplha-N-acetylglucosaminyltransferase inhibitor (0.587)
N-Acetyllactosamine synthase inhibitor (0.579)
Aryloalkyl acylamidase inhibitor (0.533)
Prolyl aminopeptidase inhibitor (0.918)
N-Acetyllactosamine synthase inhibitor (0.644)
Mannotetraose 2-aplha-N-acetylglucosaminyltransferase inhibitor (0.641)
Arylalkyl acylamidase inhibitor (0.763)
Thiopurine S-methyltrnsferase inhibitor (0.640)
Uric acid excretion stimulant (0.599)
Dopamine beta hydroxylse inhibitor (0.561)
Camphor 1,2-monooxgenase inhibitor (0.598)
Leucolysin inhibitor (0.607)
(−)-(4S)-Limonene synthase inhibitor (0.635)
CDK2/cydin A inhibitor (0.525)
Antihypoxic (0.570)
N-Carbamoyl-L-aminoacid hydrolase inhibitor (0.545)
1-Alkyl-2-acetylglycerophosphocholine esterase inhibitor (0.526)
Opine dehydrogenase inhibitor (0.575)
5
6
7
Prolyl aminopeptidase inhibitor (0.891)
Arylalkyl acylamidase inhibitor (0.667)
Mannotetraose 2-aplha-N-acetylglucosaminyltransferase inhibitor (0.697)
Antineoplastic (0.617)
N-Acetyllactosamine synthase inhibitor (0.603)
1-Alkyl-2-acetylglycerophosphocholine esterase inhibitor (0.516)
N-Carbamoyl-L-aminoacid hydrolase inhibitor (0.515)
Antineoplastic (colorectal cancer) (0.508)
Prolyl aminopeptidase inhibitor (0.764)
Antiviral (Poxvirus) (0.634)
Arylalkyl acylamidase inhibitor (0.653)
Thiopurine S-methyltrnsferase inhibitor (0.544)
Interleukin antagonist (0.540)
N-Acetyllactosamine synthase inhibitor (0.575)
Dopamine beta hydroxylse inhibitor (0.501)
Mannotetraose 2-aplha-N-acetylglucosaminyltransferase inhibitor (0.562)
2,6-Dihydroxypyridine-3-monooxygenase inhibitor (0.879)
Antiviral (Poxvirus) (0.847)
Prolyl aminopeptidase inhibitor (0.730)
Mannotetraose 2-aplha-N-acetylglucosaminyltransferase inhibitor (0.660)
Interleukin antagonist (0.599)
(Continued on next page)

THIO ANALOGS OF PYRIMIDINE BASES
2107
Table III Predicted activity (PA) values for predicted biological activity of compounds 1–9 (Continued)
Compound
Focal predicted activity (PA > 0.5)
N-Acetyllactosamine synthase inhibitor (0.619)
Nicotinate glucosyltransferase inhibitor (0.531)
Antiviral (Herpes) (0.512)
Arylalkyl acylamidase inhibitor (0.587)
8
9
Prolyl aminopeptidase inhibitor (0.848)
Thiopurine S-methyltrnsferase inhibitor (0.549)
N-Acetyllactosamine synthase inhibitor (0.575)
Arylalkyl acylamidase inhibitor (0.583)
Mannotetraose 2-aplha-N-acetylglucosaminyltransferase inhibitor (0.562)
Prolyl aminopeptidase inhibitor (0.854)
Thiopurine S-methyltrnsferase inhibitor (0.551)
N-Acetyllactosamine synthase inhibitor (0.594)
Arylalkyl acylamidase inhibitor (0.592)
Mannotetraose 2-aplha-N-acetylglucosaminyltransferase inhibitor (0.594)
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