Synthesis and Biological Evaluation of Imidazole-2-thione Fused Furazan as a New Biheterocyclic Scaffold
A new imidazole-2-thione fused furazan biheterocyclic group was synthesized and its biological activity was investigated. Nitrogen rich heterocycles, imidazole-2-thione and 1,2,5-oxadiazole (furazan) have been conveni ently fused. To accomplish this, we have improved a new strategy that silica gel s...
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Düzce University
2022-01-01
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| Series: | Düzce Üniversitesi Bilim ve Teknoloji Dergisi |
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| Online Access: | https://dergipark.org.tr/tr/download/article-file/1578760 |
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| author | Gülşah Kurt Fatih Sevgi |
| author_facet | Gülşah Kurt Fatih Sevgi |
| author_sort | Gülşah Kurt |
| collection | DOAJ |
| description | A new imidazole-2-thione fused furazan biheterocyclic group was synthesized and its biological activity was investigated. Nitrogen rich heterocycles, imidazole-2-thione and 1,2,5-oxadiazole (furazan) have been conveni ently fused. To accomplish this, we have improved a new strategy that silica gel supported solvent free micro wave dehydration of vicinal dioximes. The target furazan "N,N’-diphenyl-4H-imidazo[4,5-c]furazan-5(6H) –thio ne" [II] (DFTFrz) was obtained from (4E,5Z)-4,5-bis(hydroxyimino)-N,N’-diphenylimidazolidine-2-thione [I] (DFTD) with acceptable yield and characterized by LC-MS/MS, FT-IR and NMR spectroscopy. The biological evaluation of the obtained thiourea furazan and its precursor dioxime were investigated by antibacterial effect studies using broth microdilution and disc diffusion methods. It was observed that thioure furazan was more effective on the tested pathogenic bacteria than its precursor dioxime. The compounds did not show any effect on gram negative bacteria, while they exhibited a moderate effect on gram positive bacteria, especially Staphylococcus spp. |
| format | Article |
| id | doaj-art-7d52001695a24fe18c87f2a7b65dd8e7 |
| institution | Kabale University |
| issn | 2148-2446 |
| language | English |
| publishDate | 2022-01-01 |
| publisher | Düzce University |
| record_format | Article |
| series | Düzce Üniversitesi Bilim ve Teknoloji Dergisi |
| spelling | doaj-art-7d52001695a24fe18c87f2a7b65dd8e72025-08-20T03:54:10ZengDüzce UniversityDüzce Üniversitesi Bilim ve Teknoloji Dergisi2148-24462022-01-01101142610.29130/dubited.88066797Synthesis and Biological Evaluation of Imidazole-2-thione Fused Furazan as a New Biheterocyclic ScaffoldGülşah Kurt0https://orcid.org/0000-0001-5943-9307Fatih Sevgi1https://orcid.org/0000-0002-5049-2053AKSARAY ÜNİVERSİTESİSELÇUK ÜNİVERSİTESİA new imidazole-2-thione fused furazan biheterocyclic group was synthesized and its biological activity was investigated. Nitrogen rich heterocycles, imidazole-2-thione and 1,2,5-oxadiazole (furazan) have been conveni ently fused. To accomplish this, we have improved a new strategy that silica gel supported solvent free micro wave dehydration of vicinal dioximes. The target furazan "N,N’-diphenyl-4H-imidazo[4,5-c]furazan-5(6H) –thio ne" [II] (DFTFrz) was obtained from (4E,5Z)-4,5-bis(hydroxyimino)-N,N’-diphenylimidazolidine-2-thione [I] (DFTD) with acceptable yield and characterized by LC-MS/MS, FT-IR and NMR spectroscopy. The biological evaluation of the obtained thiourea furazan and its precursor dioxime were investigated by antibacterial effect studies using broth microdilution and disc diffusion methods. It was observed that thioure furazan was more effective on the tested pathogenic bacteria than its precursor dioxime. The compounds did not show any effect on gram negative bacteria, while they exhibited a moderate effect on gram positive bacteria, especially Staphylococcus spp.https://dergipark.org.tr/tr/download/article-file/1578760tiyoürefurazanimidazol-2-tiyoni̇kili heterohalkaantibakteriyelthioureafurazanimidazole-2-thionebiheterocyclicantibacterial |
| spellingShingle | Gülşah Kurt Fatih Sevgi Synthesis and Biological Evaluation of Imidazole-2-thione Fused Furazan as a New Biheterocyclic Scaffold Düzce Üniversitesi Bilim ve Teknoloji Dergisi tiyoüre furazan imidazol-2-tiyon i̇kili heterohalka antibakteriyel thiourea furazan imidazole-2-thione biheterocyclic antibacterial |
| title | Synthesis and Biological Evaluation of Imidazole-2-thione Fused Furazan as a New Biheterocyclic Scaffold |
| title_full | Synthesis and Biological Evaluation of Imidazole-2-thione Fused Furazan as a New Biheterocyclic Scaffold |
| title_fullStr | Synthesis and Biological Evaluation of Imidazole-2-thione Fused Furazan as a New Biheterocyclic Scaffold |
| title_full_unstemmed | Synthesis and Biological Evaluation of Imidazole-2-thione Fused Furazan as a New Biheterocyclic Scaffold |
| title_short | Synthesis and Biological Evaluation of Imidazole-2-thione Fused Furazan as a New Biheterocyclic Scaffold |
| title_sort | synthesis and biological evaluation of imidazole 2 thione fused furazan as a new biheterocyclic scaffold |
| topic | tiyoüre furazan imidazol-2-tiyon i̇kili heterohalka antibakteriyel thiourea furazan imidazole-2-thione biheterocyclic antibacterial |
| url | https://dergipark.org.tr/tr/download/article-file/1578760 |
| work_keys_str_mv | AT gulsahkurt synthesisandbiologicalevaluationofimidazole2thionefusedfurazanasanewbiheterocyclicscaffold AT fatihsevgi synthesisandbiologicalevaluationofimidazole2thionefusedfurazanasanewbiheterocyclicscaffold |