Yeni İki Hetero halkalı Bir Yapı Olarak İmidazol-2-tiyon ile Kaynaşmış Furazan Sentezi ve Biyolojik Değerlendirmesi

Abstract

İmidazole-2-tiyon grubunun furazan halkasıyla birleşmesinden oluşan iki heterohalkalı yeni bir bileşik sentez lenmiş ve biyolojik aktivitesi araştırılmıştır. Vic-dioksimlerinsilikajel destekli mikrodalga dehidrasyonunu içeren yeni bir stratejiyle, azot bakımından zengin heterohalkalar olan imidazol-2-tiyon ve 1,2,5-oksadiazol (furazan) uygun bir şekilde kaynaştırılmıştır. Hedeflenen furazan bileşiği olan “N,N’-difenil-4H-imidazo[4,5-c]furazan-5(6H)-tiyon" [II] (DFTFrz), kabul edilebilir bir verimle “(4E,5Z)-4,5-bis(hidroksimino)-N,N’-difenil imidazoli din-2-tiyon” [I] (DFTD) bileşiğinden sentezlendi ve LC-MS/MS, FT-IR ve NMR spektroskopisi metotlarıyla karakterize edildi. Elde edilen tiyoürefurazan ve çıkış maddesi dioksimin biyolojik değerlendirmesi, broth mikro dilüsyon ve disk diffüzyon yöntemlerini içeren antibakteriyel etki çalışmalarıyla araştırıldı. Tiyoüre furazanın test edilen patojenik bakteriler üzerinde öncülü olan dioksime göre daha etkili olduğu bulunmuştur. Bileşikler gram negatif bakteriler üzerinde herhangi bir etki göstermezken gram pozitif bakteriler özellikle de stafilakok türleri üzerinde orta derecede etki göstermiştir.

Keywords

• Tiyoüre
• Furazan
• Imidazol-2-tiyon
• İkili heterohalka
• Antibakteriyel

Synthesis and Biological Evaluation of Imidazole-2-thione Fused Furazan as a New Biheterocyclic Scaffold

Abstract

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.

Keywords

• Thiourea
• Furazan
• Imidazole-2-thione
• Biheterocyclic
• Antibacterial

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