Oksadiazol halkası taşıyan bazı üre ve tiyoüre bileşiklerinin sentezi ve antimikrobiyal aktivitelerinin incelenmesi
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Date
2018-10-12
Authors
Waseer, Faryal
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Publisher
Bursa Uludağ Üniversitesi
Abstract
Üre, tiyoüre ve 1,2,4-oksadiazol bileşikleri, antimikrobiyal aktivitelerinin yanı sıra anti-inflamatuar, antiviral, analjezik, fungusid, herbisit, diüretik, antihelmintik ve antitümör gibi çok çeşitli aktiviteleri ile dikkat çekmektedirler. Bu çalışmada, önemli biyolojik aktiviteye sahip olabileceğini düşündüğümüz üre, tiyoüre ve oksadiazol farmakoforlarının bir araya gelmesiyle oluşan yeni bileşiklerin sentezlenerek antimikrobiyal aktivitelerinin incelenmesi amaçlanmıştır. Çalışmanın ilk aşamasında, amidoksimlerin klorasetil klorür ile reaksiyonu sonucunda 5-klorometil-3-aril-1,2,4-oksadiazoller elde edilmiştir. Bu bileşikler, Gabriel amin sentezi ile iki basamakta 5-aminometil-3-aril-1,2,4-oksadiazol bileşiklerine dönüştürülmüştür. Hazırlanan amin bileşiklerinin THF içerisinde oda sıcaklığında fenil izosiyanat ile reaksiyonu sonucunda iyi verimlerle üre bileşikleri, fenil izotiyosiyanat ile reaksiyonundan ise tiyoüre bileşikleri sentezlenmiştir. Sentezlenen bileşiklerin yapıları FTIR,1H NMR,13C NMR ve elementel analiz teknikleriyle aydınlatılmıştır. Çalışmanın son kısmında, sentezlenen yirmi adet yeni üre ve tiyoüre bileşiğinin in vitro antimikrobiyal etkileri iki gram-pozitif (Staphylococcus aureus ATCC 25923, Staphylococcus aureus ATCC 33591) ve iki gram-negatif (Escherichia Coli ATCC 25922, Escherichia Coli ATCC 0157:H7) bakteriye karşı minimum inhibitör konsantrasyon (MİK) yöntemi ile test edilmiştir. Ciprofloxacin ve Chloramphenicol mukayese antibiyotiği olarak kullanılmıştır. Sentezlenen bileşiklerin test edilen bakterilere karşı önemli bir antimikrobiyal aktivite göstermediği belirlenmiştir.
Urea, thiourea and 1,2,4-oxadiazol compounds, are of great interest due to their different activities such as anti-inflammatory, antiviral, analgesic, fungicidal, herbicidal, diuretic, antihelminthic and antitumor along with antimicrobial activities. In this research, it was aimed to investigate the synthesis and antimicrobial activities of new compounds, which are believed to have significant biological activity by combining urea, thiourea and oxadiazole pharmacophores. In the first step, 5-chloromethyl-3-aryl-1,2,4-oxadiazoles were synthesized from the reaction of amidoximes and chloroacetyl chloride. These compounds were then converted into 5-aminomethyl-3-aryl-1,2,4-oxadiazoles by Gabriel amine synthesis in two steps. The reaction of amine compounds with phenyl isocyanate and phenyl isothiocyanate in THF at room temperature were performed to afford urea and thiourea compounds respectively, in good yields. The structures of the synthesized compounds were elucidated by FTIR, 1H NMR, 13C NMR and elemental analysis techniques. At the final step of the work, twenty new urea and thiourea compounds were tested for their in vitro antimicrobial activities, against two gram-positive (Staphylococcus aureus ATCC 25923, Staphylococcus aureus ATCC 33591) and two gram-negative (Escherichia coli ATCC 25922, Escherichia coli ATCC 0157: H7) bacterial strains by minimum inhibitory concentration (MIC) method. Ciprofloxacin and Chloramphenicol were used as reference antibiotics. It was observed that the compounds do not possess significant antimicrobial activities against the tested bacterias.
Urea, thiourea and 1,2,4-oxadiazol compounds, are of great interest due to their different activities such as anti-inflammatory, antiviral, analgesic, fungicidal, herbicidal, diuretic, antihelminthic and antitumor along with antimicrobial activities. In this research, it was aimed to investigate the synthesis and antimicrobial activities of new compounds, which are believed to have significant biological activity by combining urea, thiourea and oxadiazole pharmacophores. In the first step, 5-chloromethyl-3-aryl-1,2,4-oxadiazoles were synthesized from the reaction of amidoximes and chloroacetyl chloride. These compounds were then converted into 5-aminomethyl-3-aryl-1,2,4-oxadiazoles by Gabriel amine synthesis in two steps. The reaction of amine compounds with phenyl isocyanate and phenyl isothiocyanate in THF at room temperature were performed to afford urea and thiourea compounds respectively, in good yields. The structures of the synthesized compounds were elucidated by FTIR, 1H NMR, 13C NMR and elemental analysis techniques. At the final step of the work, twenty new urea and thiourea compounds were tested for their in vitro antimicrobial activities, against two gram-positive (Staphylococcus aureus ATCC 25923, Staphylococcus aureus ATCC 33591) and two gram-negative (Escherichia coli ATCC 25922, Escherichia coli ATCC 0157: H7) bacterial strains by minimum inhibitory concentration (MIC) method. Ciprofloxacin and Chloramphenicol were used as reference antibiotics. It was observed that the compounds do not possess significant antimicrobial activities against the tested bacterias.
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Keywords
Üre, Tiyoüre, 1,2,4-Oksadiazol, Antimikrobiyal aktivite, Minimum inhibitör konsantrasyon, Urea, Thiourea, 1,2,4-Oxadiazole, Antimicrobial activity, Minimum inhibitory concentration
Citation
Waseer, F. (2018). Oksadiazol halkası taşıyan bazı üre ve tiyoüre bileşiklerinin sentezi ve antimikrobiyal aktivitelerinin incelenmesi. Yayınlanmamış yüksek lisans tezi. Bursa Uludağ Üniversitesi Fen Bilimleri Enstitüsü.