Synthesis and antibacterial and antifungal activities of N-(tetra-O-acetyl-β-d-glucopyranosyl)thiosemicarbazones of substituted 4-formylsydnones
Background Sydnone is a heterocycle that exhibits remarkable pharmacological activities, including antimicrobial, anti-inflammatory, analgesic, antipyretic and antioxidant activities. Thiosemicarbazones are of compounds that contain the –NHCSNHN=C< linkage group and are considerable interest beca...
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Published in | BMC chemistry Vol. 9; no. 1; pp. 60 - 14 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
Cham
Springer International Publishing
19.10.2015
Springer Nature B.V |
Subjects | |
Online Access | Get full text |
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Summary: | Background
Sydnone is a heterocycle that exhibits remarkable pharmacological activities, including antimicrobial, anti-inflammatory, analgesic, antipyretic and antioxidant activities. Thiosemicarbazones are of compounds that contain the –NHCSNHN=C< linkage group and are considerable interest because they exhibit important chemical properties and potentially beneficial biological activities. Similarly, thiosemicarbazones having carbohydrate moieties also exhibit various significant biological activities.
Results
The compounds of 3-formyl-4-phenylsydnones were obtained by Vilsmeyer-Haack’s formylation reaction and were transformed into thiosemicarbazones by condensation reaction with
N
-(2,3,4,6-tetra-
O
-acetyl-β-
d
-glucopyranosyl)thiosemicarbazide. Reaction were performed in the presence glacial acetic acid as catalyst using microwave-assisted heating method. Reaction yields were 43‒85 %. The antimicrobial activities of these thiosemicarbazones were screened in vitro by using agar well diffusion and MIC methods. Among these thiosemicarbazones, compounds
4k
,
4l
,
4m
and
4n
were more active against all tested bacterial strains, especially against
S
.
epidermidis
,
B. subtilis
and
E. coli
. The MIC values in these cases are 0.156, 0.156 and 0.313 μg/mL, respectively. All compounds showed weak to moderate antifungal activity against
C. albicans
and
A. niger
than nystatin (MIC = 0.156‒0.625 μg/mL vs. MIC = 0.078 μg/mL of nystatin), and thiosemicarbazones
4l
,
4m
and
4n
exhibited significant activity with MIC = 0.156 μg/mL. These compounds also had good antifungal activity against
F. oxysporum
similarly to nystatin (MIC = 0.156 μg/mL). Among the tested compounds having halogen group
4k
,
4l
,
4m
and
4n
showed highest activity against three strains of fungal organisms.
Conclusions
In summary, we have developed a clean and efficient methodology for the synthesis of novel thiosemicarbazone derivatives bearing sydnone ring and
d
-glucose moiety; the heterocyclic and monosaccharide system being connected via ‒NH‒C(=S)NH‒N=C< linker using molecular modification approach. The methodology could be further extended and used for the synthesis of other thiosemicarbazones of biological importance. 4-Formyl-3-arylsydnone
N
-(2,3,4,6-tetra-
O
-acetyl-β-
d
-glucopyranosyl)thiosemicarbazones have been synthesized under microwave-assisted heating conditions. Almost all obtained compounds showed remarkable activities against the tested microorganisms. Among the tested compounds having halogen group
4k
,
4l
,
4m
and
4n
showed highest activity against all tested strains of bacterial and fungal organisms.
Graphical abstract:
Synthesis and antibacterial and antifungal activities of
N
-(tetra-
O
-acetyl-β-D-glucopyranosyl)thiosemicarbazones of substituted 4-formylsydnones |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 1752-153X 1752-153X 2661-801X |
DOI: | 10.1186/s13065-015-0138-8 |