Synthesis and antimicrobial activity of some S - D-glucosides of 4-mercaptopyrimidine

Article abstract of DOI:10.1080/15257770903172639

5-Acetyl-2-aryl-6-methyl-4-(2,3,4,6-tetra-O-acetyl-β- D-glucopyranosylmercapto)pyramidines 3a-c were obtained by the reaction of 5-acetyl-2-aryl-6-methyl-pyrimidine thiol 1a-c with 2,3,4,6-tetra-O-acetyl -α D-glucopyranosyl bromide (2) in aq. KOH/acetone.

Full text of DOI:10.1080/15257770903172639

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Synthesis and Antimicrobial Activity
of Some S-β-D-Glucosides of 4-
Mercaptopyrimidine
A. H. Moustafa a , H. A. Morsy a , M. G. Assy a & A. Z. Haikal a
a Department of Chemistry, Faculty of Science, Zagazig University,
Zagazig, Egypt
Published online: 04 Sep 2009.
To cite this article: A. H. Moustafa , H. A. Morsy , M. G. Assy & A. Z. Haikal (2009): Synthesis and
Antimicrobial Activity of Some S-β-D-Glucosides of 4-Mercaptopyrimidine, Nucleosides, Nucleotides
and Nucleic Acids, 28:9, 835-845
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Nucleosides, Nucleotides and Nucleic Acids, 28:835–845, 2009
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1525-7770 print / 1532-2335 online
DOI: 10.1080/15257770903172639
SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF SOME
S-β-D-GLUCOSIDES OF 4-MERCAPTOPYRIMIDINE
A. H. Moustafa, H. A. Morsy, M. G. Assy, and A. Z. Haikal
Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, Egypt
5-Acetyl-2-aryl-6-methyl-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylmercapto)pyramidines
2
3a–c were obtained by the reaction of 5-acetyl-2-aryl-6-methyl-pyrimidine thiol 1a–c with
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (2) in aq. KOH/acetone. The reaction of
1a–c with peracetylated galactose 5 and peracetylated ribose 8 under MW irradiation gave
5-acetyl-2-aryl-6-methyl-4-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosylmercapto)pyrimidine 6a–c
and 5-acetyl-2-aryl-6-methyl-4-(2,3,5-tri-O-acetyl-β-D-ribofuranosylmercapto)pyrimidines 9a–c.
The deprotection of 3a–c, 6a–c, and 9a–c in the presence of methanol and TEA/H2O yielded the
deprotected products 4a–c, 7a–c, and 10a–c. The structures of the compounds were confirmed by
1
using IR, H, 13C spectra and microanalysis. Selected members of these compounds were screened
for antimicrobial activity.
Keywords Glycosides; microwave; antimicrobial activity
INTRODUCTION
The pyrimidines and their nucleosides are interesting classes in medic-
inal and agricultural chemistry. Some pyrimidine nucleosides are known as
antiviral,[1–3] antibacterials,[4,5] antitumor,[6] antipyretic,[7] antiinflamma-
tory drugs,[8] pesticides,[9] and plant growth regulators.[10]
Glycosylthio-heterocycles have attracted much attention because of their
abilities to function as biological inhibitors, inducers, and ligands for affinity
of chromatography of carbohydrate-process enzymes and proteins.[11] The
utility of microwave (MW) as a nonconventional energy source has advan-
tages such as significant rate enhancements of reactions, higher product
yields, and greater selectivity of organic reactions.[12–14] The combination
of solvent-free reaction conditions and microwave irradiation has also been
investigated.[15–17]
Received 13 May 2009; accepted 30 June 2009.
Address correspondence to Ahmed H. Moustafa, Chemistry Department, Faculty of Science,
Zagazig University, Zagazig, Egypt. E-mail: ah hu mostafa@yahoo.com
835

836
A. H. Moustafa et al.
SCHEME 1
RESULTS AND DISCUSSION
The syntheses of 5–acetyl-6-methyl-2-arylpyrimidine-4-thiols 1a–c
have been achieved as reported in literature.[18] Reaction of 1a–c
with glycosyl bromide 2 in the presence of aqueous potassium
hydroxide/acetone[4,5] gave 5-acetyl-6-methyl-2-aryl-4-(2,3,4,6 -tetra-O-
acetyl-β-D-glycopyranosylthio)pyrimidines (3a–c) (Scheme 1). Irradiation
of 1a–c with 5 in the presence of silica gel as a solid support in MW
oven[4,19] for 10 minutes gave the corresponding thiogalactosides 6a–c in
40–45% yield (Scheme 1).
The structure of compounds 3a–c was confirmed on the basis of their
elemental analysis and spectral data. Their IR spectra showed a band at
1765–1745 cm−1 for the acetoxy carbonyl groups in addition to a band at
1695cm−1 due to the carbonyl of 5-aceylpyrimidine.
1
The H NMR spectrum of 3a showed the presence of signals at δ
1.53, 1.96, 2.00, and 2.02 ppm characteristic for 4 CH3 of OAc groups, in
addition to 2 CH3 at δ 2.36, 2.58 ppm and a doublet at δ 6.23 ppm for
ꢁ
ꢁ
anomeric proton with J 1 ,2 = 8.97 Hz, which confirmed the presence of
the β-configuration. The 13C NMR spectrum of 3a showed peak at δ 80.1
=
ppm, characteristic for anomeric carbon, and absence of C S group, which
indicates the formation of S-glycoside not N-glycoside.
1
The H NMR spectrum of 3b and 3c showed similar results. Also
the glycosides 6a–c showed spectral characteristic conforming their

Some S-β-D-Glucosides of 4-Mercaptopyrimidine
837
SCHEME 2
β-configuration. On the other hand, reaction of 1a–c with 8 under MW
irradiation in the presence of silica gel as a solid support[4,20] for 8 minutes
gave the corresponding ribosides 9a–c in 40–45% yield (Scheme 2).
1
The H NMR spectrum of 9a showed signals at δ 2.06, 2.07, and 2.15
ppm for 3 CH3 of OAc groups, and doublet at δ 6.46 ppm for anomeric
ꢁ
ꢁ
proton with coupling constant J 1 ,2 = 2.80 Hz indicating the presence of
β-configuration. Similarly 9b and 9c gave similar results. Deprotection of
the previous prepared S-glucosides 3a–c, 6a–c, and 9a–c using triethylamine
in presence of methanol and few drops of water[4,5,20] gave the deprotected
glycosides 4a–c, 7a–c, and 10a–c (Schemes 1and 2).
The 1H, 13C NMR spectra for 4a–c showed the absence of the four signals
of the 4 OAc groups and presence of signals at δ 4.53, 5.11, 5.24, and 5.51
ppm for 4 OH groups of sugar moieties, in addition of doublet at δ 5.61,
5.68, and 6.26 ppm for the anomeric protons of 4a–c. The IR spectra of 4a–c
showed the appearance of the broad band at 3417 cm−1 for 4 OH groups.
Similar results were obtained for 7a–c and 10a–c.
Antimicrobial Activity
Compound 3c showed higher activity against B. subtitlis as gram positive
and E. coli as gram negative bacteria, while 3a,b and 6b showed only
moderate activity. Compounds 3 and 9a showed activity towards fungi (e.g.,
Penicillium sp. and aspergillus sp.). Compounds 6a,c and 9b,c did not show
any activity against the tested microorganisms (Table 1).
EXPERIMENTAL
All melting points are uncorrected and were measured using an
Electrothermal IA 9100 apparatus. Thin layer chromatography (TLC)
was performed on Merck Silica Gel 60F254 with detection by UV light
and charring with H2SO4/EtOH (5:95); The IR spectra (KBr disc) were
recorded on a Pye Unicam Sp-3-300 and Shimadzu FTIR 8101 PC infrared

838
A. H. Moustafa et al.
TABLE 1 Antimicrobial activity of tested compounds (inhibition zones [mm],
minimum inhibitory concentration [µg/mL])
Compound no.
E. Coli
B. Subtilis
Penicillium Sp.
Aspergillus Sp.
3a
3b
3c
6a
6b
6c
9a
9b
9c
—
—
10
—
—
—
—
—
—
15
10
25
—
5
—
10
—
—
15
—
—
—
—
—
10
—
—
10
—
—
—
—
—
8
—
—
spectrophotometer. The ultraviolet (UV) spectra were recorded by UV-
160A, UV-visible recording spectrometer Shimadzu using EtOH 95% as a
1
solvent. The H and 13C NMR spectra were recorded on a Varian Mercury
VX-NMR 300 & 100 MHz spectrometer. Chemical shifts are expressed on
the δ(ppm) scale using TMS as the standard and coupling-constant values
are given in Hz. Elemental analyses were determined on a Perkin Elmer
240.
General Methods for Preparation of Glucosides
Method A
To a solution of pyrimidinethiol 1a–c (0.01 mol) in aq. KOH [0.01 mol
in distilled water (6 mL)] was added a solution of 2,3,4,6-tetra-O-acetyl-α-D-
glucopyranosyl bromide (2) (0.011 mol) in acetone (30 mL). The reaction
mixture was stirred at room temperature and followed by tlc until the
reaction was finished (4.5–5 hours), the reaction mixture was evaporated
under reduced pressure and the residue was washed with distilled water to
remove potassium bromide. The product was dried and crystallized from
the appropriate solvent.
Method B
A mixture of pyrimidinethiol 1a–c (0.001 mol) and (0.001 mol) of per
acetylated galactose (5) or ribose (8) was dissolved in methylene chloride,
then 1 gm of silica gel (200–400 mesh) was added, the solvent was removed
by evaporation, and then the dried residue was transferred into a glass
beaker and irradiated for (8–10 minutes) in a domestic microwave oven.
The product was extracted with methylene chloride, evaporated to dryness,
and crystallized from appropriate solvent.
5-Acetyl-6-methyl-2-phenyl-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-
thio)pyrimidine (3a). Method A: yield 26%. As colorless crystals from
1
ethanol; m.p. 105–107◦C; λmax = 300 nm. H NMR (DMSO-d6, 300 MHz):

Some S-β-D-Glucosides of 4-Mercaptopyrimidine
839
δ 1.53, 1.96, 2.00, 2.02 (4s, 12 H, 4 CH3CO), 2.36 (s, 3 H, CH3 pyrimidine),
2.58 (s, 3 H, CH3CO pyrimidine), 4.00 (m, 1 H, H-5ꢁ), 4.13(dd, 1 H, J6 ,5
ꢁꢁ
ꢁ
= 2.10, J6 ,6 = 12.32 Hz, H-6ꢁꢁ), 4.26 (dd, 1 H, J6 ,5 = 5.96, J6 ,6 = 12.3
ꢁꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁꢁ
Hz, H-6ꢁ), 5.12 (t, 1 H, J4 ,3 = 8.78, J4 ,5 = 9.13 Hz, H-4ꢁ), 5.31 (t, 1 H,
ꢁ
ꢁ
ꢁ
ꢁ
J2 ,1 = 7.70, J2 ,3 = 9.20 Hz, H-2ꢁ), 5.63 (t, 1 H, J3 ,2 = 9.20, J3 ,4 = 8.78
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
Hz, H-3ꢁ), 6.23 (d, 1 H, J1 ,2 = 8.97 Hz, H-1 ), 7.56 (m, 3 H, Ar H), 8.58
ꢁ
ꢁ
−
(m, 2 H, Ar H). 13C NMR (DMSO-d6, 100 MHz): δ 20.8, 21.1, 21.2, 21.4,
−
23.8, 32.2 (6 CH3), 62.8 (C-6ꢁ), 69.2 (C-2ꢁ), 69.8 (C-4ꢁ), 73.8 (C-3ꢁ), 75.9
(C-5ꢁ), 80.1 (C-1ꢁ), 129.4, 129.6, 130.9, 132.4, 136.7, 162.54, 163.1, 163.6,
−
=
=
170.1, 170.4, 170.6 and 202.8 (Ar C, 2 C N and 5 C O). Anal. Calcd for
C27H30N2O10S (574.6): C, 56.44; H, 5.26; N, 4.88. Found: C, 56.68; H, 5.31;
N, 5.03.
5-Acetyl-6-methyl-2-(4-methoxyphenyl)-4-(2,3,4,6-tetra-O-acetyl-β-D-
glucopyranosylthio)pyrimidine (3b). Method A: yield 24%. As colorless
crystals from ethanol; m.p. 100–103◦C; λmax = 301.4 nm. 1H NMR
(DMSO-d6, 300 MHz): δ 1.54, 1.95, 2.00, 2.02 (4s, 12 H, 4 CH3CO), 2.34
(s, 3 H, CH3 pyrimidine), 2.59 (s, 3 H, CH3CO pyrimidine), 3.89 (s, 3 H,
OCH3), 3.98 (m, 1 H, H-5ꢁ), 4.12 (dd, 1 H, J6 ,5 = 2.10, J6 ,6 = 12.3 Hz,
ꢁꢁ
ꢁ
ꢁꢁ
ꢁ
H-6ꢁꢁ), 4.26 (dd, 1 H, J6 ,5 = 5.96, J6 ,6 = 12.3 Hz, H-6ꢁ), 5.12 (t, 1 H, J4 ,3
=
ꢁ
ꢁ
ꢁ
ꢁꢁ
ꢁ
ꢁ
8.97, J4 ,5 = 9.13 Hz, H-4ꢁ), 5.31 (t, 1 H, J2 ,1 = 7.90, J2 ,3 = 9.22 Hz, H-2ꢁ),
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
5.62 (t, 1 H, J3 ,2 = 9.22, J3 ,4 = 8.78 Hz, H-3ꢁ), 6.24 (d, 1 H, J1 ,2 = 8.87
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
−
−
Hz, H-1 ), 7.10 (d, 2 H, J = 9.0 Ar H), 8.40 (d, 2 H, J = 9.0 Hz, Ar H).
13C NMR (DMSO-d6, 100 MHz): δ 20.8, 21.1, 21.2, 21.4, 23.9, 32.3 (6 CH3),
56.2 (OCH3), 62.8 (C-6ꢁ), 69.2 (C-2ꢁ), 69.8 (C-4ꢁ), 73.8 (C-3ꢁ), 75.9 (C-5ꢁ),
80.0 (C-1ꢁ), 129.2, 130.0, 131.3, 131.7, 162.3, 163.0, 163.1, 163.6, 170.1,
−
=
=
170.2, 170.4, 170.6 and 202.7 (Ar C, 2 C N and 5 C O). Anal. Calcd for
C28H32N2O11S (604.63): C, 55.62; H, 5.33; N, 4.63. Found: C, 55.50; H,
5.68; N, 4.60.
5-Acetyl-2-(4-chlorophenyl)-6-methyl-4-(2,3,4,6-tetra-O-acetyl-β-D-
glucopyranosylthio)pyrimidine (3c). Method A: yield 34%. As colorless
crystals from ethanol; m.p. 104–106◦C; λmax = 300 nm. IR (KBr): 1749
−1
−1
1
=
=
(C O, esters) cm , 1697(C O, acetyl) cm . H NMR (DMSO-d6, 300
MHz): δ 1.53, 1.95, 2.00, 2.02 (4s, 12 H, 4 CH3CO), 2.45 (s, 3 H, CH3
pyrimidine), 2.55 (s, 3 H, CH3CO pyrimidine), 3.98 (m, 1 H, H-5ꢁ), 4.12
(dd, 1 H, J6 ,5 = 2.10, J6 ,6 = 12.3 Hz, H-6ꢁꢁ), 4.27 (dd, 1 H, J6 ,5 = 5.96, J6 ,6
ꢁꢁ
ꢁ
ꢁꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁꢁ
= 12.3 Hz, H-6ꢁ), 4.92 (t, 1 H, J4 ,3 = 8.97, J4 ,5 = 9.13 Hz, H-4ꢁ), 5.08 (t, 1 H,
ꢁ
ꢁ
ꢁ
ꢁ
J2 ,1 = 7.90, J2 ,3 = 9.22 Hz, H-2ꢁ), 5.67 (t, 1 H, J3 ,2 = 9.22, J3 ,4 = 8.78 Hz,
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
H-3ꢁ), 6.21(d, 1 H, J1 ,2 = 7.89 Hz, H-1 ), 7.59 (d, 2 H, J = 8.90 Ar H), 8.49
ꢁ
ꢁ
ꢁ
−
(d, 2 H, J = 8.90 Ar H). 13C NMR (DMSO-d6, 100 MHz): δ 20.2, 20.3, 20.4,
−
22.8, 22.9, 31.3 (6 CH3), 61.9 (C-6ꢁ), 68.2 (C-2ꢁ), 68.9 (C-4ꢁ), 72.9 (C-3ꢁ),
74.9 (C-5ꢁ), 79.2 (C-1ꢁ), 128.8, 128.9, 130.3, 130.4, 134.7, 136.5, 160.6, 162.7,
−
=
=
162.9, 169.4, 169.5, 169.6 and 201.9 (Ar C, 2 C N and 5 C O). Anal.
Calcd for C27H29 ClN2O10S (609.04): C, 53.25; H, 4.80; N, 6.40. Found: C,
53.12; H, 4.57; N, 6.21.

840
A. H. Moustafa et al.
5-Acetyl-6-methyl-2-phenyl-4-(β-D-glucopyranosylthio)pyrimidine (4a).
General method for deprotection of acetyl groups: Triethylamine (1ml) was added
to 10 ml a solution of glucosides or ribosides (0.001mol) in (MeOH/H2O).
The mixture was stirred overnight at room temperature; it was evaporated
under reduced pressure and co-evaporated with MeOH until the excess
of Et3N was removed. The residue was then crystallized from the proper
solvent to give the desired product with yield >85%. Colourless crystals
from ethan−o1l; m.p. 115–117◦C; IR (KBr): 3417 (br. 4 OH) cm−1 and 1689
1
=
(C O) cm . H NMR (DMSO-d6/D2O, 300 MHz): δ 2.46 (s, 3 H, CH3
pyrimidine), 2.60 (s, 3 H, CH3CO pyrimidine), 3.24–3.85 (m, 6 H, H-6ꢁ,
H-6ꢁꢁ, H-5ꢁ, H-4ꢁ, H-3ꢁ and H-2ꢁ), 5.69 (d, 1 H, J1 ,2 = 8.97 Hz, H-1ꢁ),7.45 (m,
ꢁ
ꢁ
3 H, Ar H), 8.42 (m, 2 H, Ar H). 13C NMR (DMSO-d6,300 MHz): δ 22.5,
31.4 (2 CH3), 61.6 (C-6ꢁ), 69.6 (C-2ꢁ), 71.7 (C-4ꢁ), 78.5 (C-3ꢁ), 81.8 (C-5ꢁ),
83.0 (C-1ꢁ), 128.2, 128.8, 128.9, 130.3, 131.4, 136.3, 161.6, 163.7 and 202.6
−
−
−
=
=
(Ar C, 2 C N and C O). Anal. Calcd for C19H22N2O6S (406.45): C, 56.15;
H, 5.46; N, 6.89. Found: C, 55.91; H, 5.55; N, 6.93.
5-Acetyl-6-methyl-2-(4-methoxyphenyl)-4-(β-D-glucopyranosylthio)
pyrimidine (4b). As for 4a, colorless crystals from ethanol; m.p. 110–111◦C;
−1
IR (KBr): 3415 (br. 4 OH) cm−1 and 1690 (C O) cm . 1H NMR
=
(DMSO-d6/D2O, 300 MHz): δ 2.45 (s, 3 H, CH3 pyrimidine), 2.62 (s, 3 H,
CH3CO pyrimidine), 3.23–3.85 (m, 6 H, H-6ꢁ, H-6ꢁꢁ, H-5ꢁ, H-4ꢁ, H-3ꢁ and
H-2ꢁ), 3.89 (s, 3 H, OCH3), 6.21 (d, 1 H, J1 ,2 = 8.90 Hz, H-1ꢁ), 7.10 (d, 2
ꢁ
ꢁ
−
−
H, J = 8.62 Hz, Ar H), 8.40 (d, 2 H, J = 8.62 Hz, Ar H). Anal. Calcd for
C20H24N2O7S (436.48): C, 55.03; H, 5.54; N, 6.42. Found: C, 55.23; H, 5.44;
N, 6.50.
5-Acetyl-2-(4-chlorophenyl)-6-methyl-4-(β-D-glucopyranosylthio)pyrimi-
dine (4c). As for 4a, colorless crystals from ethanol; m.p. 114–116◦C;
−1
IR (KBr): 3417 (br. 4 OH) cm−1 and 1700 (C O) cm . 1H NMR
=
(DMSO-d6, 300 MHz): δ 2.46 (s, 3 H, CH3 pyrimidine), 2.59 (s, 3 H, CH3CO
pyrimidine), 3.13–3.46 (m, 6 H, H-6ꢁ, H-6ꢁꢁ, H-5ꢁ, H-4ꢁ, H-3ꢁ and H-2ꢁ), 4.53
(t, 1 H, J = 3.56 Hz, OH-6ꢁ), 5.11 (d, J = 4.34 Hz, 1 H, OH-4ꢁ), 5.24 (d, 1
H, J = 5.24 Hz, OH-3ꢁ), 5.51 (d, 1 H, J = 4.96 Hz, OH-2ꢁ), 6.24 (d, 1 H,
ꢁ
ꢁ
ꢁ
−
J1 ,2 = 8.89 Hz, H-1 ), 7.60 (d, 2 H, J = 8.91 Hz, Ar H), 8.39 (d, 2 H, J =
8.91 Hz, Ar H). 13C NMR (DMSO-d6, 100 MHz): δ 22.4, 31.3 (2 CH3), 60.7
−
(C-6ꢁ), 69.6 (C-2ꢁ), 71.6 (C-4ꢁ), 78.4 (C-3ꢁ), 81.9 (C-5ꢁ), 83.1 (C-1ꢁ), 128.9,
−
=
130.0, 130.4, 135.2, 136.3, 160.6, 161.7, 163.9 and 202.5 (Ar C, 2 C N and
=
C O). Anal. Calcd for C19H21 ClN2O6S (440.90): C, 51.76; H, 4.80; N, 6.35.
Found: C, 51.42; H, 4.36; N, 6.17.
5-Acetyl-6-methyl-2-phenyl-4-(2,3,4,6-tetra-O-acetyl-β-D-galactopyran-
osylthio)pyrimidine (6a). Method B: yield 40%. As colorless crystals from
ethanol; m.p. 102–103◦C; λmax = 303.2 nm. 1H NMR (DMSO-d6, 300 MHz):
δ 1.50, 1.95, 2.03, 2.13 (4s, 12 H, 4 CH3CO), 2.46 (s, 3 H, CH3 pyrimidine),
2.59 (s, 3 H, CH3CO pyrimidine), 3.95 (m, 1 H, H-5ꢁ), 4.12 (dd, 1 H, J6 ,5
=
ꢁꢁ
ꢁ
6.50, J6 ,6 = 12.0 Hz, H-6ꢁꢁ), 4.25 (dd, 1 H, J6 ,5 = 5.60, J6 ,6 = 12.0 Hz, H-6ꢁ),
ꢁ
ꢁꢁ
ꢁ
ꢁ
ꢁ
ꢁꢁ

Some S-β-D-Glucosides of 4-Mercaptopyrimidine
841
5.21 (t, 1 H, J3 ,2 = 10.0, J3 ,4 = 3.50 Hz, H-3ꢁ), 5.41 (t, 1 H, J2 ,1 = 8.20, J2 ,3
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
= 10.0 Hz, H-2ꢁ), 5.62 (t, 1 H, J4 ,3 = 3.50, J4 ,5 = 1.00 Hz, H-4ꢁ), 6.26 (d, 1
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
H, J1 ,2 = 8.20 Hz, H-1 ), 7.57 (m, 3 H, Ar H), 8.56 (d, 2 H, Ar H). 13C
NMR (DMSO-d6, 100 MHz): δ 20.1, 20.3, 20.4, 22.7, 22.9, 31.3 (6 CH3), 62.0
(C-6ꢁ), 69.1 (C-2ꢁ), 68.9 (C-4ꢁ), 73.8 (C-3ꢁ), 75.9 (C-5ꢁ), 80.1 (C-1ꢁ), 129.3,
129.6, 130.8, 132.3, 136.7, 162.5, 163.1, 163.5, 170.2, 170.3, 170.4, 170.6 and
ꢁ
ꢁ
−
−
−
=
=
202.6 (Ar C, 2 C N and 5 C O). Anal. Calcd for C27H30N2O10S (574.6):
C, 56.44; H, 5.26; N, 4.88. Found: C, 56.53; H, 5.33; N, 5.23.
5-Acetyl-6-methyl-2-(4-methoxyphenyl)-4-(2,3,4,6-tetra-O-acetyl-β-D-
galactopyranosylthio)pyrimidine (6b). Method B: yield 41%. As colorless
crystals from ethanol; m.p. 98–99◦C; λmax = 302.8 nm. 1H NMR (DMSO-d6,
300 MHz): δ 1.51, 1.59, 2.03, 2.13 (4s, 12 H, 4 CH3CO), 2.49 (s, 3 H, CH3
pyrimidine), 2.57 (s, 3 H, CH3CO pyrimidine), 3.85 (s, 3 H, OCH3), 3.95
(m, 1H, H-5ꢁ), 4.13 (dd, 1 H, J6 ,5 = 6.50, J6 ,6 = 12.0 Hz, H-6ꢁꢁ), 4.26 (dd,
ꢁꢁ
ꢁ
ꢁ
ꢁꢁ
1 H, J6 ,5 = 5.60, J6 ,6 = 12.0 Hz, H-6ꢁ), 5.22 (t, 1 H, J3 ,2 = 10.0, J3 ,4
=
ꢁ
ꢁ
ꢁ
ꢁꢁ
ꢁ
ꢁ
ꢁ
ꢁ
3.50 Hz, H-3ꢁ), 5.41 (t, 1 H, J2 ,1 = 8.20, J2 ,3 = 10.0 Hz, H-2ꢁ), 5.62 (t, 1
ꢁ
ꢁ
ꢁ
ꢁ
H, J4 ,3 = 3.50, J4 ,5 = 1.00 Hz, H-4ꢁ), 6.26 (d, 1 H, J1 ,2 = 8.22 Hz, H-1ꢁ),
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
7.08 (d, 2 H, J = 8.63 Hz, Ar H), 8.48 (d, 2 H, J = 8.63 Hz, Ar H). 13C
NMR (DMSO-d6, 100 MHz): δ 20.1, 20.2, 20.4, 22.6, 22.8, 31.2 (6 CH3),
56.2 (OCH3), 61.8 (C-6ꢁ), 66.4 (C-2ꢁ), 70.9 (C-4ꢁ), 72.4 (C-3ꢁ), 74.4 (C-5ꢁ),
79.6 (C-1ꢁ), 128.3, 129.2, 130.4, 131.7, 161.4, 162.1, 162.7, 169.4, 169.5,
−
−
−
=
=
169.7, 169.8, 170.0 and 201.8 (Ar C, 2 C N and 5 C O). Anal. Calcd for
C28H32N2O11S (604.63): C, 55.62; H, 5.33; N, 4.63. Found: C, 55.51; H, 5.48;
N, 4.60.
5-Acetyl-2-(4-chlorophenyl)-6-methyl-4-(2,3,4,6-tetra-O-acetyl-β-D-gal-
actopyranosylthio)pyrimidine (6c). Method B: yield 45%. As colorless crystals
1
from ethanol; m.p. 106–109◦C; λmax = 301.4 nm. H NMR (DMSO-d6,
300 MHz): δ 1.49, 1.58, 2.03, 2.14 (4s, 12 H, 4 CH3CO), 2.48 (s, 3 H, CH3
pyrimidine), 2.59 (s, 3 H, CH3CO pyrimidine), 3.98 (m, 1 H, H-5ꢁ), 4.14
(dd, 1 H, J6 ,5 = 6.50, J6 ,6 = 12.0 Hz, H-6ꢁꢁ), 4.27 (dd, 1 H, J6 ,5 = 5.60,
ꢁꢁ
ꢁ
ꢁ
ꢁꢁ
ꢁ
ꢁ
J6 ,6 = 12.0 Hz, H-6ꢁ), 5.23 (t, 1 H, J3 ,2 = 10.0, J3 ,4 = 3.50 Hz, H-3ꢁ), 5.42
ꢁ
ꢁꢁ
ꢁ
ꢁ
ꢁ
ꢁ
(t, 1 H, J2 ,1 = 8.20, J2 ,3 = 10.0 Hz, H-2ꢁ), 5.65 (t, 1 H, J4 ,3 = 3.50, J4 ,5
=
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
1.00 Hz, H-4ꢁ), 6.36 (d, 1 H, J1 ,2 = 8.22 Hz, H-1ꢁ), 7.53 (d, 2 H, J = 8.90 Hz,
ꢁ
ꢁ
Ar H), 8.49 (d, 2 H, J = 8.90 Hz, Ar H). 13C NMR (DMSO-d6, 100 MHz):
δ 20.1, 20.2, 20.4, 22.6, 22.8, 31.1 (6 CH3), 61.6 (C-6ꢁ), 66.8 (C-2ꢁ), 69.6
(C-4ꢁ), 70.5 (C-3ꢁ), 70.6 (C-5ꢁ), 79.3 (C-1ꢁ), 128.5, 130.1, 134.4, 134.5, 160.3,
−
−
−
=
162.1, 162.6, 168.5, 168.9, 169.2, 169.3, 169.5 and 201.6 (Ar C, 2 C N and
=
5 C O). Anal. Calcd for C27H29 ClN2O10S (609.04): C, 53.25; H, 4.80; N,
6.40. Found: C, 53.52; H, 4.78; N, 6.33.
5-Acetyl-6-methyl-2-phenyl-4-(β-D-galactopyranosylthio) pyrimidine (7a).
As for 4a, colorless crystals from ethanol; m.p. 118–119◦C; IR (KBr): 3417
−1
1
(br 4 OH) cm−1 and 1690 (C O) cm . H NMR (DMSO-d6/D2O, 300
=
MHz): δ 2.45 (s, 3 H, CH3 pyrimidine), 2.59 (s, 3 H, CH3CO pyrimidine),
3.23–3.84 (m, 6 H, H-6ꢁ, H-6ꢁꢁ, H-5ꢁ, H-4ꢁ, H-3ꢁ and H-2ꢁ), 6.21 (d, 1 H, J1 ,2
=
ꢁ
ꢁ

842
A. H. Moustafa et al.
ꢁ
−
−
8.40 Hz, H-1 ), 7.57 (m, 3 H, Ar H), 8.53 (m, 2 H, Ar H). Anal. Calcd for
C19H22N2O6S (406.45): C, 56.15; H, 5.46; N, 6.89. Found: C, 55.90; H, 5.45;
N, 6.93.
5-Acetyl-6-methyl-2-(4-methoxyphenyl)-4-(β-D-galactopyranosyl-
thio)pyrimidine (7b). As for 4a, colorless crystals from ethanol−; 1m.p.
1
112–114◦C; IR (KBr): 3415 (br 4 OH) cm−1 and 1695 (C O) cm . H
=
NMR (DMSO-d6/D2O, 300 MHz): δ 2.45 (s, 3 H, CH3 pyrimidine), 2.59 (s,
3 H, CH3CO pyrimidine), 3.24–3.75 (m, 6 H, H-6ꢁ, H-6ꢁꢁ, H-5ꢁ, H-4ꢁ, H-3ꢁ
and H-2ꢁ), 3.85 (s, 3 H, OCH3), 6.23 (d, 1H, J1 ,2 = 8.51 Hz, H-1ꢁ), 7.52 (d,
ꢁ
ꢁ
−
−
2 H, J = 8.90 Hz, Ar H), 8.48 (d, 2 H, J = 8.90 Hz, Ar H). Anal. Calcd for
C20H24N2O7S (436.48): C, 55.03; H, 5.54; N, 6.42. Found: C, 55.43; H, 5.44;
N, 6.52.
5-Acetyl-2-(4-chlorophenyl)-6-methyl-4-(β-D-galactopyranosylthio)
pyrimidine (7c). As for 4a, colorless crystals from ethanol; m.p. 119–120◦C;
−1
IR (KBr): 3418 (br. 4 OH) cm−1 and 1692 (C O) cm . 1H NMR
=
(DMSO-d6/D2O, 300 MHz): δ 2.45 (s, 3 H, CH3 pyrimidine), 2.58 (s, 3 H,
CH3CO pyrimidine), 3.35–3.85 (m, 6ꢁ H, H-6ꢁ, H-6ꢁꢁ, H-5ꢁ, H-4ꢁ, H-3ꢁ and
H-2ꢁ), 6.22 (d, 1 H, J1 ,2 = 8.45 Hz, H-1 ), 7.53 (d, 2 H, J = 8.90 Hz, Ar H),
ꢁ
ꢁ
−
−
8.48 (d, 2 H, J = 8.90 Hz, Ar H). Anal. Calcd for C19H21 ClN2O6S (440.90):
C, 51.76; H, 4.80; N, 6.35. Found: C, 51.44; H, 4.32; N, 6.27.
5-Acetyl-6-methyl-2-phenyl-4-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl-
thio)pyrimidine (9a). Method B: yield 41%; as colorless crystals from
methanol; m.p. 111–113◦C; λmax = 300 nm. 1H NMR (DMSO-d6, 300 MHz):
δ 2.06, 2.07, 2.15 (3s, 9 H, 3 CH3CO), 2.43 (s, 3 H, CH3 pyrimidine), 2.59
ꢁ
ꢁ
ꢁ
ꢁꢁ
(s, 3 H, CH3CO pyrimidine), 4.10 (dd, 1 H, J5 ,4 = 3.40, J5 ,5 = 11.6 Hz,
H-5ꢁ), 4.16 (dd, 2 H, J5 ,4 = 3.60, J5 ,5 = 11.6 Hz, H-5ꢁꢁ), 4.41 (m, 1 H, H-4ꢁ),
ꢁꢁ
ꢁ
ꢁꢁ
ꢁ
5.54 (t, 1 H, J3 ,2 = 2.71, J3 ,4 = 6.62 Hz, H-3ꢁ), 5.63 (dd, 1 H, J2 ,1 = 2.60,
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
J2 ,3 = 2.80 Hz, H-2ꢁ), 6.46 (d, 1 H, J1 ,2 = 2.80 Hz, H-1ꢁ), 7.45–8.40 (m, 5 H,
ꢁ
ꢁ
ꢁ
ꢁ
−
Ar H). Anal. Calcd for C24H26N2O8S (502.54): C, 57.36; H, 5.52; N, 5.57.
Found: C, 57.14; H, 5.11; N, 5.75.
5-Acetyl-6-methyl-2-(4-methoxyphenyl)-4-(2,3,5-tri-O-acetyl-β-D-
ribofuranosylthio)pyrimidine (9b). Method B: yield 36%, as colorless
1
crystals from methanol ; m.p. 107–109◦C; UV; λmax = 299 nm. H NMR
(DMSO-d6, 300 MHz): δ 2.05, 2.07, 2.16 (3s, 9 H, 3 CH3CO), 2.51 (s, 3 H,
CH3CO pyrimidine), 2.62 (s, 3 H, CH3 pyrimidine), 3.34 (s, 3 H, OCH3),
ꢁ
ꢁ
ꢁ
ꢁ
ꢁꢁ
ꢁꢁ
ꢁ
4.10 (dd, 1 H, J5 ,4 = 3.40, J5 ,5 = 11.6 Hz, H-5 ), 4.14 (dd, 1 H, J5 ,4 = 3.60,
J5 ,5 = 11.6 Hz, H-5ꢁꢁ), 4.41 (m, 1 H, H-4ꢁ), 5.43 (t, 1 H, J3 ,2 = 2.71, J3 ,4
=
ꢁ
ꢁꢁ
ꢁ
ꢁ
ꢁ
ꢁ
6.62 Hz, H-3ꢁ), 5.56 (dd, 1 H, J2 ,1 = 2.60, J2 ,3 = 2.80 Hz, H-2ꢁ), 6.43 (d, 1
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ)
ꢁ
ꢁ
−
H, J1 ,2 = 2.75 Hz, H-1 7.61 (d, 2 H, J = 8.90 Hz, Ar H), 8.31 (d, 2 H, J =
−
8.90 Hz, Ar H). Anal. Calcd for C25H28N2O9S (532.56): C, 56.38; H, 5.30;
N, 5.26. Found: C, 56.10; H, 5.32; N, 5.19.
5-Acetyl-2-(4-chlorophenyl)-6-methyl-4-(2ꢁ,3ꢁ,5ꢁ-tri-O-acetyl-β-D-
ribofuranosylthio)pyrimidine (9c). Method B: yield 40%, as colorless
crystals from methanol ; m.p. 105–107◦C; UV; λmax 299 nm. H NMR
1

Some S-β-D-Glucosides of 4-Mercaptopyrimidine
843
(DMSO-d6, 300 MHz): δ 2.05, 2.07, 2.16 (3s, 9 H, 3 CH3CO), 2.62 (s, 3
H, CH3CO pyrimidine), 2.51 (s, 3 H, CH3 pyrimidine), 4.06 (dd, 1 H,
ꢁ
ꢁ
ꢁ
ꢁ
ꢁꢁ
ꢁꢁ
ꢁ
ꢁꢁ
ꢁ
J5 ,4 = 3.40, J5 ,5 = 11.6 Hz, H-5 ), 4.12 (dd, 1 H, J5 ,4 = 3.60, J5 ,5
=
11.6 Hz, H-5ꢁꢁ), 4.45 (m, 1 H, H-4ꢁ), 5.42 (t, 1 H, J3 ,2 = 2.71, J3 ,4 = 6.62
ꢁ
ꢁ
ꢁ
ꢁ
Hz, H-3ꢁ), 5.55 (dd, 1 H, J2 ,1 = 2.60, J2 ,3 = 2.80 Hz, H-2ꢁ), 6.42 (d, 1 H,
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ)
ꢁ
ꢁ
−
J1 ,2 = 2.60 Hz, H-1 , 7.60 (d, 2 H, J = 8.80 Hz, Ar H), 8.34 (d, 2 H, J
= 8.80 Hz, Ar H). 13C NMR (DMSO-d6, 100 MHz); δ 20.7, 20.8, 21.0,
−
23.4, 31.8 (5 CH3), 62.7 (C-5ꢁ), 70.5 (C-3ꢁ), 75.6 (C-2ꢁ), 79.6 (C-4ꢁ), 85.4
(C-1ꢁ), 129.3, 130.2, 135.2, 137.0, 160.9, 163.3, 164.1, 166.5, 169.7, 169.8,
−
=
=
170.3 and 202.1 (Ar C, 2 C N and 4 C O). Anal. Calcd for C24H25
ClN2O8S (536.98): C, 53.68; H, 4.69; N, 5.22. Found: C, 53.61; H, 4.81;
N, 4.93.
5-Acetyl-6-methyl-2-phenyl-4-(β-D-ribofuranosylthio)pyrimidine (10a).
As for 4a, c−o1lorless crystals from ethanol; m.p. 124–126◦C. IR (KBr): 3419
−1
1
=
(3 OH) cm , 1692 (C O) cm . H NMR (DMSO-d6/D2O, 300 MHz): δ
2.41 (s, 3 H, CH3 pyrimidine), 2.54 (s, 3 H, CH3CO pyrimidine), 3.46 -3.73
(m, 2 H, H-5ꢁ 5 Prime;), 3.97 (m, 1 H, H-4ꢁ), 4.12 (dd, 1 H, J3 ,4 = 6.60,
ꢁ
ꢁ
J3 ,2 = 2.70 Hz, H-3ꢁ), 4.23 (dd, 1 H, J2 ,1 = 2.60, J2 ,3 = 2.70 Hz, H-2ꢁ),
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
−
6.21 (d, 1 H, J1 ,2 = 2.80 Hz, H-1 ), 7.53–8.37 (m, 5 H, Ar H). Anal. Calcd
for C189H20N2O5S (376.43): C, 57.43; H, 5.36; N, 7.44. Found: C, 57.40; H,
4.98; N, 7.47.
5-Acetyl-6-methyl-2-(4-methoxyphenyl)-4-(β-D-ribofuranosylthio) pyrimi-
dine (10b). As for 4a, colorless crystals from ethanol; m.p. 117–119◦C; IR
−1
−1
1
=
(KBr): 3420 (3 OH) cm , 1695 (C O) cm . H NMR (DMSO-d6/D2O,
300 MHz): δ 2.45 (s, 3 H, CH3 pyrimidine), 2.54 (s, 3 H, CH3CO pyrimi-
dine), 3.41–3.83 (m, 2 H, H-5ꢁ H-5 Prime;), 3.89 (s, 3 H, OCH3), 3.96 (m,
1 H, H-4ꢁ), 4.10 (dd, 1 H, J3 ,4 = 6.59, J3 ,2 = 2.70 Hz, H-3ꢁ), 4.20 (t, 1 H,
ꢁ
ꢁ
ꢁ
ꢁ
J2 ,1 = 2.60, J2 ,3 = 2.70 Hz, H-2ꢁ), 6.22 (d, 1 H, J1 ,2 = 2.8 Hz, H-1ꢁ), 7.54
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
(d, 2 H, J = 8.90 Hz, Ar H), 8.36 (d, 2 H, J = 8.90 Hz, Ar H). 13C NMR
(DMSO-d6, 100 MHz): δ 20.0, 31.0 (2 CH3), 56.3 (OCH3), 61.5 (C-5ꢁ), 70.4
(C-3ꢁ), 75.3 (C-2ꢁ), 75.8 (C-4ꢁ), 74.0 (C-1ꢁ), 120.9, 121.3, 128.7, 129.8, 136.5,
−
−
−
=
=
136.9, 161.9, 169.9, and 201.8 (Ar C, 2 C N and C O). Anal. Calcd for
C19H22 N2O6S (406.45): C, 56.15; H, 5.46; N, 6.89. Found: C, 56.43; H, 5.32;
N, 6.70.
5-Acetyl-2-(4-chlorophenyl)-6-methyl-4-(β-D-ribofuranosylthio)pyrimi-
dine (10c). As for 4a, −c1olourless crystals f−ro1 m ethanol; m.p. 123–125◦C; IR
1
=
(KBr): 3422 (OH) cm , 1690 (C O) cm . H NMR (DMSO-d6/D2O, 300
MHz): δ 2.43 (s, 3 H, CH3 pyrimidine), 2.57 (s, 3 H, CH3CO pyrimidine),
3.42–3.83 (m, 2 H, H-5ꢁ 5Prime;), 3.95 (m, 1 H, H-4ꢁ), 4.12 (dd, 1 H,
J3 ,4 = 6.58, J3 ,2 = 2.75 Hz, H-3ꢁ), 4.20 (t, 1 H, J2 ,1 = 2.60, J2 ,3 = 2.70
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
ꢁ
Hz, H-2ꢁ), 6.23 (d, 1 H, J1 ,2 = 2.80 Hz, H-1ꢁ),7.25 (d, 2 H, J = 8.98
ꢁ
ꢁ
−
−
Hz, Ar H), 8.05 (d, 2 H, J = 8.98 Hz, Ar H). Anal. Calcd for C18H19
ClN2O5S (410.87): C, 52.62; H, 4.66; N, 6.82. Found: C, 52.34; H, 4.54;
N, 6.76.

844
A. H. Moustafa et al.
Antibacterial Screening
The antimicrobial activities of some newly synthesized compounds were
screened for their antibacterial activity against three species of bacteria,
namely (E. coli) as Gram positive, (B. Subtilis) as Gram negativeve and
(Penicillium Sp.) and (Asperagillus Sp.) as fungi, using saturated disks accord-
ing to the a dapted method.[21] The tested compounds were dissolved in
chloroform to get a solution of 1 mg/mL concentration. The inhibition
zones were measured in (mm) at the end of an incubation period of 48
hours at 37◦C. Chloroform showed no inhibition zones. The fungi cultures
were maintained on dextrose agar medium.
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