Synthesis and antibacterial and antifungal activities of N-(tetra-O-acetyl-β-d-glucopyranosyl)thiosemicarbazones of substituted 4-formylsydnones.
| Title: | Synthesis and antibacterial and antifungal activities of N-(tetra-O-acetyl-β-d-glucopyranosyl)thiosemicarbazones of substituted 4-formylsydnones. |
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| Authors: | Thanh ND; Faculty of Chemistry, VNU University of Science, 19 Le Thanh Tong, Hoan Kiem, Ha Noi, Vietnam.; Duc HT; Faculty of Chemistry, Hanoi University of Industry, Minh Khai, Tu Liem, Ha Noi, Vietnam.; Duyen VT; Faculty of Chemistry, VNU University of Science, 19 Le Thanh Tong, Hoan Kiem, Ha Noi, Vietnam.; Tuong PM; Faculty of Chemistry, VNU University of Science, 19 Le Thanh Tong, Hoan Kiem, Ha Noi, Vietnam.; Van Quoc N; Faculty of Chemistry, Vinh University, 182 Le Duan, Vinh, Nghe An Vietnam. |
| Source: | Chemistry Central journal [Chem Cent J] 2015 Oct 19; Vol. 9, pp. 60. Date of Electronic Publication: 2015 Oct 19 (Print Publication: 2015). |
| Publication Type: | Journal Article |
| Language: | English |
| Journal Info: | Publisher: BioMed Central Country of Publication: England NLM ID: 101314213 Publication Model: eCollection Cited Medium: Print ISSN: 1752-153X (Print) Linking ISSN: 1752153X NLM ISO Abbreviation: Chem Cent J Subsets: PubMed not MEDLINE |
| Imprint Name(s): | Publication: [London, United Kingdom] : BioMed Central; Original Publication: London : Chemistry Central Ltd., in association with BioMed Central, c2007- |
| Abstract: | 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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| Contributed Indexing: | Keywords: Antibacterial; Antifungal; Microwave-assisted synthesis; Sydnones; Thiosemicarbazones; d-Glucose |
| Entry Date(s): | Date Created: 20151023 Date Completed: 20151022 Latest Revision: 20200930 |
| Update Code: | 20260130 |
| PubMed Central ID: | PMC4611015 |
| DOI: | 10.1186/s13065-015-0138-8 |
| PMID: | 26491468 |
| Database: | MEDLINE |
Journal Article