Synthesis of new 1,2,4-Triazole-5-thiones and their thioglycoside derivatives as potential antibacterial agents

Article abstract of DOI:10.1080/10426507.2013.789877

Abstract The glycosylation of 1,2,4-triazole-5-thiones has been performed with peracetylated β-pyranosyl bromide in the presence of potassium carbonate. The synthesized compounds were tested for their antimicrobial activity against bacterial (Gram-negative and Gram-positive) and yeasts strains in vitro. The synthetic compounds showed different inhibition zones against tested bacterial and yeasts strains. Among them, compounds which possessed 2-furyl and p-bromophenyl moieties showed the best results against Acinetobacter calcoaceticus ATCC 23055.

Full text of DOI:10.1080/10426507.2013.789877

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Synthesis of New 1,2,4-Triazole-5-
Thiones and Their Thioglycoside
Derivatives as Potential Antibacterial
Agents
Karim Akbari Dilmaghani a , Fazel Nasuhi Pur a , Nima Hoseini Jazani
b , Asma Alavi a , Zahra Niknam a & Farrin Mirfakhraee c
a Department of Chemistry, Faculty of Science , Urmia University ,
Urmia , 57159 , Iran
b Department of Microbiology, Faculty of Medicine , Urmia Medical
Science University , Urmia , Iran
c Institute of Standard and Industrial Research of Iran , Urmia , Iran
Accepted author version posted online: 25 Jun 2013.Published
online: 03 Dec 2013.
To cite this article: Karim Akbari Dilmaghani , Fazel Nasuhi Pur , Nima Hoseini Jazani , Asma Alavi ,
Zahra Niknam & Farrin Mirfakhraee (2014) Synthesis of New 1,2,4-Triazole-5-Thiones and Their
Thioglycoside Derivatives as Potential Antibacterial Agents, Phosphorus, Sulfur, and Silicon and the
Related Elements, 189:1, 81-87, DOI: 10.1080/10426507.2013.789877
To link to this article: http://dx.doi.org/10.1080/10426507.2013.789877
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Phosphorus, Sulfur, and Silicon, 189:81–87, 2014
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426507.2013.789877
SYNTHESIS OF NEW 1,2,4-TRIAZOLE-5-THIONES
AND THEIR THIOGLYCOSIDE DERIVATIVES AS
POTENTIAL ANTIBACTERIAL AGENTS
Karim Akbari Dilmaghani,1 Fazel Nasuhi Pur,1
Nima Hoseini Jazani,2 Asma Alavi,1 Zahra Niknam,1 and Farrin
Mirfakhraee3
1Department of Chemistry, Faculty of Science, Urmia University, Urmia 57159,
Iran
2Department of Microbiology, Faculty of Medicine, Urmia Medical Science
University, Urmia, Iran
3Institute of Standard and Industrial Research of Iran, Urmia, Iran
GRAPHICAL ABSTRACT
Abstract Abstract The glycosylation of 1,2,4-triazole-5-thiones has been performed with per-
acetylated β-pyranosyl bromide in the presence of potassium carbonate. The synthesized com-
pounds were tested for their antimicrobial activity against bacterial (Gram-negative and Gram-
positive) and yeasts strains in vitro. The synthetic compounds showed different inhibition zones
against tested bacterial and yeasts strains. Among them, compounds which possessed 2-furyl
and p-bromophenyl moieties showed the best results against Acinetobacter calcoaceticus ATCC
23055.
Keywords 1,2,4-Triazole-thione; β-pyranosyl; thioglycoside; antimicrobial; yeasts strain;
in vitro
INTRODUCTION
The majority of carbohydrates found in nature or biological systems exist as gly-
coconjugates in which the monosaccharide units are joined via O-, N-, or S-glycosidic
Received 30 January 2013; accepted 20 March 2013.
We gratefully acknowledge the University of Urmia for providing a fellowship to us for the present work
(project no: 008/E/90).
Address correspondence to Karim Akbari Dilmaghani, Department of Chemistry, Faculty of Science,
Urmia University, Urmia 57159, Iran. E-mail: kadilmaghani@gmail.com; k.adilmaghani@urmia.ac.ir
81

82
K. A. DILMAGHANI ET AL.
bonds. Thioglycosides have received considerable attention, because they are widely em-
ployed as biological inhibitors,1–4 inducers,5,6 and ligands7,8 for affinity chromatography
of carbohydrate-processing enzymes and proteins. They have excellent chemoselectivity in
glycosylation processes as both donors and acceptors9 particularly via reaction processes
that involve active and latent glycosylation protocols.10 The thioglycosyl heterocycles are
sufficiently stable under a variety of reaction conditions and have the ability to be readily
converted into a variety of other functionalities.11,12
Multivalent display of carbohydrates is frequently used as a method to increase
affinities13,14 in various contexts such as the binding of bacteria,15–18 bacterial toxins,19–21
galectins,22,23 and other lectins.24,25 These properties may affect medicinal effect of antibi-
otic agents.
On the other hand, the 1,2,4-triazole nucleus is found in many drug structures such
as anastrozole, estazolam, ribavirin, and triazolam. In addition, these compounds show
antiseptic, analgesic, and anticonvulsant properties.26–28 Moreover, sulfur-containing hete-
rocycles represent an important group of sulfur compounds that are promising for use in
practical applications. Among these heterocycles, thione-substituted 1,2,4-triazole ring sys-
tems have been well studied and so far a variety of biological activities have been reported
for a large number of their derivatives, such as antibacterial,29,30 antifungal,31,32 antituber-
cular,33 antimycobacterial,34 anticancer,35,36 diuretic,37,38 and hypoglycemic39 properties.
Therefore, it is interesting to report the synthesis of a new series of compounds in
which the glycosyl moieties have been used as carriers for the heterocycles having the
triazole ring.
In our previous work,40 we reported the synthesis of new series of antimycobacterial
agents with heterocyclic nucleus, whereas in the present work, we report the synthesis
of new groups of antibacterial agents in which the heterocyclic moiety is coupled to
monosaccharide units.
RESULTS AND DISCUSSION
A general approach to the synthesis of thioglycosides may proceed via the direct
introduction of the heterocyclic thiol part, either by an SN1 or SN2 displacement reaction
of an anomeric leaving group, in a manner similar to O-glycosylation reactions. Alterna-
tively, two (or more) step procedures may be employed in which a thiol group is primarily
introduced on the anomeric center and then its reaction with an electrophile will lead
to the target thioglycoside. The anomeric halide group in a glycosyl donor can be effi-
ciently displaced by a thiol group linked to a heterocycle under the influence of a basic
catalyst.
In our attempt to obtain 1-bromide sugars, at the first step D-galactose and D-glucose
were treated with acetic anhydride in pyridine at room temperature and gave 1,2,3,4,6-penta-
O-acetyl-β-galactose and 1,2,3,4,6-penta-O-acetyl-β-glucose, respectively. The anomeric
bromination of these compounds with hydrogen bromide in acetic acid gave 2,3,4,6-tetra-
O-acetyl-α-galactopyrnosyl bromide (d1) and 2,3,4,6-tetra-O-acetyl-α-glucopyranosyl bro-
mide (d2), respectively.
The reaction of aryl carboxylic acid hydrazides with aryl isothiocyanate in ethanol
gave the corresponding thiosemicarbazides which were cyclized in alkaline media to yield
1,2,4-triazole-5-thiones (a1–6). Thioglycosyl triazoles (b1–6, c1–6) were synthesized by the
SN2 reaction of 1,2,4-triazole-5-thiones (a1–6) and the peracetylated β-pyranosyl bromides
(d1,2) in the presence of potassium carbonate as a weak base in dry acetone.

NEW 1,2,4-TRIAZOLE-5-THIONES & THIOGLYCOSIDE DERIVATIVES
83
The structure of thioglycosyl triazoles was confirmed by appropriate spectroscopic
methods such as 1H NMR, 13C NMR, and high resolution mass spectroscopy (HRMS). The
anomeric protons of compounds (b1–6, c1–6) were assigned to the doublet at 5.63–6.41 ppm
with J1,2 = 8.4–9.6 Hz, confirming the β-configuration.
The in vitro antibacterial activity of the synthesized compounds in DMSO against
some of most important Gram-positive and Gram-negative infectious agents is shown in
Tables S1–S3 (Supplemental Materials available online).
The synthetic compounds showed different inhibition zones against tested bacterial
and yeasts strains. Pseudomonas aeruginosa and E. coli (Gram-negative) and Enterococcus
faecalis (Gram-positive) were resistant (“R”) to all prepared compounds. On the other
hand, Acinetobacter calcoaceticus was sensitive to compounds of the a set, especially
a4 and a6 as well as the b group, especially b4, b5, and b6, and compounds from the
c series, especially c1 and c6 (Tables S1–S3). As shown in the tables, these compounds
showed high antibacterial effects in comparison with different kinds of antibiotics such as
Ampicillin and Trimethoprim/Sulfamethoxazole which are normally used for treating such
infections.
Staphylococcus aureus (Gram-positive, relatively resistant to antimicrobials) showed
limited sensitivity to only a6 (with low antibacterial effects in comparison with Ery-
thromycin and Cephalothin). On the other hand, S. aureus was resistant to all compounds
from the a, b, and c series (Tables S1–S3, Supplemental Materials available online).
Only compound a6 of the a set exerted comparable activity to reference antimicrobial
Nystatin against Candida albicans and its activity in comparison with Fluconazole was just
slightly weaker (Table S1, Supplemental Materials available online). Also, all compounds
from the b and c series showed limited activity against this microorganism (Tables S2 and
S3).
Candida tropicalis was resistant to all synthetic compounds of the c and b series,
and in the a set only a6 exhibited a low activity which was not comparable to the standard
compounds of Fluconazole and Nystatin (Table S 1).
In general, compounds from the b set showed more antimicrobial activity than two
other series. Thioglycoside derivatives of 1,2,4-triazole-5-thiones (series b and c) were
more active against Acinetobacter calcoaceticus ATCC 23055 than “parent” 1,2,4-triazole-
5-thiones (a set), this consideration confirmed the relation between glyco-conjugation and
increasing of antiproliferative activity of antibiotic agents.
The best results in the tables belonged to a6 that showed high activity against A.
calcoaceticus (24 mm) as well as Candida albicans (20 mm). Also, its glycoconjugates (b6
and c6) possessed this property only against A. calcoaceticus. Among them, c6 was the best
choice (25 mm) for A. calcoaceticus as an antibacterial agent.
Thioglyco conjugation of 1,2,4-triazole-5-thiones (a group) increased (except a6) the
antifungal property of the corresponding compounds from the b and c groups, whereas
that was only limited activity against C. albicans (Tables S1–S3, Supplemental Materials
available online). As shown in the tables, galactose was more effective than glucose in
mentioned increasing for thioglycosides from the b and c sets (except for glycoconjugates
of a1 and a2).
Likewise, a6, b6, and c6, compounds a1, a4 and sugar-coupled of them showed high
activity against A. calcoaceticus too. Going over the structure of these synthetic compounds
confirmed that the existence of 2-furyl or phenyl instead of a m-nitrophenyl group as Ar
and p-bromophenyl instead of a phenyl group as Arꢁ (Scheme 1) increased their antibacterial
activity against A. calcoaceticus. We realized this by comparing the structures of a3, a6 and

84
K. A. DILMAGHANI ET AL.
Scheme 1 General synthetic pathway for the synthesis of thioglycosyl triazoles.
their thioglycosides with the values of their antibacterial activity in vitro as well as a1 and
a4 or a2 and a5. The presence of a m-nitrophenyl group as Ar in structures of a2, a5 and
their corresponding sugar derivatives decreased their antibacterial activity in comparison
with the rest of the synthetic compounds.
EXPERIMENTAL
1H and 13C NMR spectra were recorded on a Bruker AVANCE-300 spectrometer at
300 and 75 MHz, respectively in CDCl3 using TMS as the internal standard. High-resolution
mass spectra were obtained with a HPLC-Q-TOF system equipped with Q-TOF micro
mass spectrometer (dual ESI). Melting points were measured on a Philip Harris C4954718
apparatus without calibration. Optically active samples were analyzed by EHARTNACK
apparatus (Paris, France) at 20◦C in dichloromethane. Thin layer chromatography (TLC)
analyses were carried out on silica gel plates. All chemicals were purchased from Merck
and used as received.
1,2,4-Triazole-5-thiones (a1–6) were synthesized according to the literature proce-
dure.41 Peracetylated α-pyranosyl bromides (d1,2) were prepared according to the published
methods.42,43
Synthesis of Thioglycosyl Triazoles (b1–6 and c1–6
)
A mixture of compound a1–6 (1 mmol) and K2CO3 (2 mmol, 0.276 g) in dry acetone
(25 mL) and 5 drops of DMF were stirred for 1 h, then glycosyl bromide d1,2 (2.2 mmol)
was added. Stirring was continued overnight, and then the reaction mixture was heated
under reflux for 2–4 h. After cooling, the mixture was filtered, the solids were washed with
acetone, the filtrate was evaporated under reduced pressure, and the crude product was
recrystallized from ethanol.
We report herein the spectroscopic data of compounds b1 and c1, but the rest of
compounds were unambiguously characterized by similar spectroscopic methods. Charac-
terization data are presented in the online Supplemental Materials.
4,5-Diphenyl-3-(2,3,4,6-tetra-O-acetyl-β-D-1-thio-galactopyranose)-1,2,4-
triazole (b1)
◦
20
1
White powder, Yield: 42%; mp. 201–203 C; [α]D = –1◦ (c = 1.0, CH2Cl2). H
NMR: 1.98 (s, 3H, OAc), 2.02 (s, 3H, OAc), 2.04 (s, 3H, OAc), 2.06 (s, 3H, OAc), 4.03–4.35

NEW 1,2,4-TRIAZOLE-5-THIONES & THIOGLYCOSIDE DERIVATIVES
85
(m, 3H, H-6a, H-6b, H-5), 5.23–5.35 (m, 1H, H-2), 5.45–5.60 (m, 1H, H-4), 5.94 (t, 1H,
J2,3 = J3,4 = 9.6, H-3), 6.30 (d, 1H, J1,2 = 8.4, H-1), 7.20–7.68 (m, 10H, ArH); 13C NMR:
20.57, 20.72, 20.78, 20.83 (4 × OCOCH3), 61.32 (C-6), 66.97 (C-4), 67.57 (C-2), 71.51
(C-3), 73.63 (C-5), 83.27 (C-1), 124.99, 128.23, 128.57, 128.66, 129.73, 129.93, 130.84,
134.69, 150.56 (Triazole), 169.18 (C−S), 169.90, 170.34, 170.41, 171.35 (4 × OCOCH3);
HRMS (ESI), m/z: Calculated, 584.1703. C28H29N3O9S [M+H]+. Found, 584.1785.
4,5-Diphenyl-3-(2,3,4,6-tetra-O-acetyl-β-D-1-thio-glucopyranose)-1,2,4-
triazole (c1)
White powder, Yield: 77%; mp. 261–262 ◦C; [α]D = 2◦ (c = 1.0, CH2Cl2). 1H NMR:
20
1.97 (s, 3H, OAc), 2.05 (s, 3H, OAc), 2.07 (s, 3H, OAc), 2.09 (s, 3H, OAc), 3.95–4.10 (m,
1H, H-6a), 4.11–4.26 (m, 1H, H-6b), 4.27–4.41 (m, 1H, H-5), 5.29 (t, 1H, J1,2 = J2,3
=
9.3, H-2), 5.46 (t, 1H, J2,3 = J3,4 = 9.3, H-4), 5.86 (t, 1H, J2,3 = J3,4 = 9.3, H-3), 6.33 (d,
1H, J1,2 = 9, H-1), 7.20–7.67 (m, 10H, ArH); 13C NMR: 20.61 (2C), 20.71, 20.79 (4 ×
OCOCH3), 61.70 (C-6), 67.71 (C-4), 69.79 (C-2), 73.48 (C-3), 74.61 (C-5), 82.73 (C-1),
124.88, 128.20, 128.50, 128.62, 129.75, 129.97, 130.89, 134.63, 150.42 (Triazole), 169.07
(C−S), 169.44, 170.09, 170.69, 171.44 (4 × OCOCH3); HRMS (ESI), m/z: Calculated,
584.1703. C28H29N3O9S [M+H]+. Found, 584.1787.
Bacterial Strains
The antibacterial activity of the compounds was tested against Gram-positive and
Gram-negative bacterial strains including Enterococcus faecalis ATCC 29212 and Staphy-
lococcus aureus ATCC 25923, as well as Gram-negative strains covering Acinetobacter
calcoaceticus ATCC 23055, Escherichia coli ATCC 25922, and Pseudomonas aeruginosa
ATCC 27853 and yeast strains including one clinical isolate of Candida albicans and one
isolate of Candida tropicalis.
Preparation of Test Compounds and Antibacterial Activity Assays
The antibacterial activity of the compounds was assayed with the method of Parekh
et al.44 with some modifications. In brief, solutions with 10 μg/μL concentrations of each
compound in DMSO (Merck) were being prepared. A loop full of defined strain was in-
oculated in 25 mL of Nutrient Broth medium (BBL) and was incubated for 24 h in 37◦C.
Mueller Hinton Agar (MHA) (Merck) plates were prepared according to the manufacturer’s
recommendations by dissolving 34 g of the medium in 1000 mL of distilled water. Thirty
milliliters of autoclaved media were added into a 10 cm plate. Inoculation of each strain
was done by the pour-plate method. Two hundred microliter of the activated strain was
added into the MHA medium in 45◦C and after proper homogenization was distributed into
a Petri-dish. The complete microbiological procedures were performed in a laminar airflow
to maintain aseptic conditions. After solidification of the media, a well was made in the
MHA with a sterile glass tube (6 mm) and 50 μL of drug compound was added into the well.
Fifty microliter of DMSO was inoculated into another well as negative control. The an-
tibacterial activities of drug compounds were determined by measuring the inhibition zone
formed around each well against defined bacterial strain. Erythromycin and Cephalothin

86
K. A. DILMAGHANI ET AL.
were used as standard drugs for antibacterial effects against Gram-positive bacteria, Ampi-
cillin and Trimethoprim/sulfamethoxazole were used as standards for Gram-negative bac-
teria, and Fluconazole and Nystatin were used as standard drugs for antibacterial effects
against yeasts. All strains were resistant to DMSO (negative control).
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