Synthesis Of Novel 2,5-Disubstitue 1,3,4-Oxadiazol Compounds

Yıl 2020, Cilt: 10 Sayı: 2, 330 - 338, 15.04.2020

Meltem Tan

https://doi.org/10.17714/gumusfenbil.612725

Öz

Compounds containing
1,3,4-oxadiazole ring in the structure have a broad spectrum of biological activity.
Generally; antibacterial, antifungal, analgesic, anti-inflammatory, antiviral,
anticancer, antidiabetic, antihelmintic, anticonvulsant effect has been
demonstrated by recent studies. Therefore, in this study, the reaction of
hydrazine hydrate and pirocaine have been investigated and synthesis of
benzohydrazide derivative molecules has been carried out.
Then, by the ring closure of these compounds in the
presence of acetic anhydride and acetic acid, the synthesis of 1,3,4-oxadiazole
compounds which were not previously mentioned in the literature and containing
different groups at 2,5 positions was carried out. Investigation of
antibacterial and antifungal properties of synthesized compounds were performed
with Escherichia coli ATCC 36218, Staphylococcus aureus ATCC 25923 and Candida
albicans ATCC 10231 microorganisms. It was observed that those compounds containing lipophilic acetate group bound
to phenyl ring had antibacterial and antifungal properties.

Anahtar Kelimeler

Aromatic, Biological Activity, Heteroyclic, Oxadiazole

Yeni 2,5-Disubstitüe 1,3,4-Oksadiazol Bileşiklerinin Sentezi

Öz

Yapısında
1,3,4- oksadiazol halkası içeren bileşikler geniş bir biyolojik aktivite
spektrumuna sahiptir. Genel olarak; antibakteriyel, antifungal, analjezik,
antiinflamatuar, antiviral, antikanser, antidiabetik, antihelmintik,
antikonvülsan etki gösterdikleri son yıllarda yapılan çalışmalarla ortaya
konulmuştur. Bu nedenle bu çalışmada öncelikle prokain bileşiğinden yola
çıkılarak hidrazin hidrat ile reaksiyonları incelendi ve benzohidrazit türevi moleküllerin
sentezi yapıldı. Sonrasında bu bileşiklerin asetik anhidrit ve asetik asit
varlığında halka kapanma reaksiyonları ile daha önce literatürde yer almayan ve
2,5 konumlarında farklı gruplar içeren 1,3,4-oksadiazol bileşiklerinin sentezi
gerçekleştirildi. Sentezlenen bileşiklerin antibakteriyel ve antifungal
özelliklerinin araştırılması Escherichia
coli ATCC 36218, Staphylococcus
aureus ATCC 25923 ve Candida albicans
ATCC 10231 mikroorganizmaları ile yapıldı. Bileşikler içinde fenil
halkasına bağlı lipofilik asetat grubu bulunduranların antibakteriyel ve
antifungal özelliklere sahip olduğu gözlendi.

Anahtar Kelimeler

Aromatik, Biyolojik Aktivite, Heterosiklik, Oksadiazol

Kaynakça

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