İndollerin bazı dioksim türevlerinin sentezi, mikrodalga ile furazanlara dönüştürülmesi ve antimikrobiyal etkilerinin incelenmesi
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Tarih
2010-09-30
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Yayıncı
Selçuk Üniversitesi Fen Bilimleri Enstitüsü
Erişim Hakkı
info:eu-repo/semantics/openAccess
Özet
İndollerle ilgili heterohalkalı yapılar birçok doğal maddenin yapısında bulunmakta ve ilginç biyolojik aktiviteler göstermektedir. Son yıllarda deniz canlılarından çok sayıda bis-indol alkaloitleri izole edilerek antitümör, antimikrobiyal, antiviral etkileri incelenmiş ve biyolojik özellikleri ortaya çıkarılmıştır. Bu çalışmada indollerle ilişkili olarak potansiyel biyoaktif özellikte 30 yeni bileşik sentezlenerek yapıları; 1H-NMR, 13C-NMR, FT-IR, LC-MS ve elementel analiz teknikleriyle aydınlatılmış ve biyolojik özellikleri, antibakteriyel etki çalışmalarıyla ortaya konmuştur. Çalışmanın ilk aşamasında 15 indol türevi dioksim sentezlenmiştir. Dioksimler ilk defa bu tez kapsamında uygulanan oldukça kolay bir metot ile elde edilmiştir. Bu metotta, indoller elektronca zengin 3 numaralı karbon atomundan kloroglioksimler ile etkileşerek, C-C bağlı ?-dioksimler elde edilmektedir. Bu metot ile 1-metil indol, 2-metil indol ve 1,2-dimetil indol bileşiklerinin; dikloroglioksim, anti-klorofenilglioksim, anti-p-klorofenilkloroglioksim, anti-p-tolilkloroglioksim ve anti-klorometilglioksim ile reaksiyonlarından 3 tanesi bis-indol dioksim olmak üzere 15 yeni dioksim sentezlenmiştir. Çalışmanın ikinci aşaması ise bir önceki aşamada sentezlenen dioksimlerin biyoaktif furazanlara (1,2,5-oksadiazol) dönüşümünü içermektedir. 15 yeni indol türevi furazan bileşiği, dioksimlerin mikrodalga ışınlarıyla dehidrasyonu sonucu elde edilmiştir. Kapalı kap mikrodalga sistemi kullanılarak gerçekleştirilen bu metot furazan sentezinde ilk defa uygulanan bir tekniktir. Çalışmanın son kısmında indol türevi dioksim ve furazanların in-vitro antibakteriyel etkileri, disk difüzyon yöntemi ve mikrodilüsyon broth metodu kullanılarak incelenmiştir. Minimum inhibitör konsantrasyon (MİK) değerleri hem spektrofotometrik olarak hem de bir redoks indikatörü olan TTC kullanılarak kolorimetrik metotla bulunmuştur. Sentezlenen bileşiklerden bazıları test mikroorganizmalarına karşı 2-64 ?g/mL aralığında MİK değerleriyle antibakteriyel aktivite göstermiştir.
Heterocyclic structures, which are related with indoles, exist in various natural matters and exhibit interesting biological activities. In recent years, large quantities of bis-indole alkaloids have been isolated from marine organisms; their antitumor, antimicrobial and antiviral effects have been examined and their biological properties have been determined. In the present study, potentially-active 30 new compounds related with indoles were synthesized and characterized in terms of various techniques, such as 1H-NMR, 13C-NMR, FT-IR, LC-MS, and elemental analyses. Biological properties of the well-characterized compounds were investigated through antibacterial effect studies. In the first stage of the study, 15 indole derivative dioximes were synthesized. Dioximes were obtained through a rather simple method that was first used within the scope of this thesis. In this method, indoles react with chloroglyoximes from number 3 carbon atom, which is rich in electrons, and thus C-C bound ?-dioximes are obtained. With this method, 15 new dioximes which three of them bis-indole were synthesized by react 1-methyl indole, 2-methyl indole and 1,2-dimethyl indole with dichloroglyoxime, anti-chlorophenylglyoxime, anti-p-chlorophenylchloroglyoxime, anti-p-tolylchloro-glyoxime and anti-chloromethylglyoxime. The second stage of the study includes conversion of dioximes that were synthesized in the first stage into bioactive furazanes (1,2,5-oxadiazoles). 15 new indole derivatives of furazan compounds were obtained via dehydration of dioximes under microwave irradiations. This method, which was carried out using the closed vessel microwave system, was a technique that was used for the first time in furazan synthesis. In the final section of the study, antibacterial effects of indole derivative dioximes and furazanes were examined using the disc diffusion method and microdilution broth method. Minimum inhibitory concentration (MIC) values were found via both spectrophotometrically and with colorimetric method using TTC, which is a redox indicator. Some of the synthesized compounds were exhibited antibacterial activities against test microorganisms with MIC values ranging between 2-64 ?g/mL.
Heterocyclic structures, which are related with indoles, exist in various natural matters and exhibit interesting biological activities. In recent years, large quantities of bis-indole alkaloids have been isolated from marine organisms; their antitumor, antimicrobial and antiviral effects have been examined and their biological properties have been determined. In the present study, potentially-active 30 new compounds related with indoles were synthesized and characterized in terms of various techniques, such as 1H-NMR, 13C-NMR, FT-IR, LC-MS, and elemental analyses. Biological properties of the well-characterized compounds were investigated through antibacterial effect studies. In the first stage of the study, 15 indole derivative dioximes were synthesized. Dioximes were obtained through a rather simple method that was first used within the scope of this thesis. In this method, indoles react with chloroglyoximes from number 3 carbon atom, which is rich in electrons, and thus C-C bound ?-dioximes are obtained. With this method, 15 new dioximes which three of them bis-indole were synthesized by react 1-methyl indole, 2-methyl indole and 1,2-dimethyl indole with dichloroglyoxime, anti-chlorophenylglyoxime, anti-p-chlorophenylchloroglyoxime, anti-p-tolylchloro-glyoxime and anti-chloromethylglyoxime. The second stage of the study includes conversion of dioximes that were synthesized in the first stage into bioactive furazanes (1,2,5-oxadiazoles). 15 new indole derivatives of furazan compounds were obtained via dehydration of dioximes under microwave irradiations. This method, which was carried out using the closed vessel microwave system, was a technique that was used for the first time in furazan synthesis. In the final section of the study, antibacterial effects of indole derivative dioximes and furazanes were examined using the disc diffusion method and microdilution broth method. Minimum inhibitory concentration (MIC) values were found via both spectrophotometrically and with colorimetric method using TTC, which is a redox indicator. Some of the synthesized compounds were exhibited antibacterial activities against test microorganisms with MIC values ranging between 2-64 ?g/mL.
Açıklama
Anahtar Kelimeler
MİK, Antibakteriyel, Mikrodalga sentez, 1,2,5-oksadiazoller, Furazanlar, Dioksimler, İndoller, MIC, Antibacterial, Microwave synthesis, 1,2,5-oxadiazoles, Furazanes, Dioximes, Indoles
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Künye
Sevgi, F. (2010). İndollerin bazı dioksim türevlerinin sentezi, mikrodalga ile furazanlara dönüştürülmesi ve antimikrobiyal etkilerinin incelenmesi. Selçuk Üniversitesi, Yayımlanmış doktora tezi, Konya.
