Synthesis and Antimicrobial Activity of Some Taurinamide Derivatives

Year 2017, Volume: 21 Issue: 2, 361 - 370, 01.04.2017

Özlem Akgül , İsmail Öztürk Abdurrahman Aygül Şafak Ermertcan

https://doi.org/10.12991/marupj.300894

Abstract

In this study, a series of taurinamide derivatives were synthesized

and screened for their antimicrobial activity. The structures of

the newly synthesized compounds 11-15 were evaluated by

1H NMR, IR, MS-APCI and elemental analysis. Compounds

(1-15) were tested against standard strains of Gram(+),

Gram(−) bacteria and fungi by using disc diffusion and broth

microdilution methods. Although disc diffusion method did

not show any comparable results due to the solubility properties

of the compounds; microdilution method results indicated that

title compounds showed from poor to good activity against

only Enterococcus faecalis. It can be concluded that phtalimido

moiety, secondary aryl sulphonamide group and electrondonating

group substitution on phenyl ring are essential for

the antibacterial activity. Among the tested compounds, para

substituted methyl and methoxy derivatives of N-phenyl-2-

phthalimidotaurinamide (4, 7), displayed equipotent activity

compared to standard drug gentamicin.

Keywords

Taurinamide, N-substituted-2- phtalimidoethanesulfonamide, antibacterial, Enterococcus faecalis, microdilution

Bazı taurinamit türevi bileşiklerin sentezi ve antimikrobiyel etkileri

Abstract

Bu çalışmada, bir seri taurinamit türevi sentezlenmiş ve

antimikrobiyal aktiviteleri test edilmiştir. Yeni sentezlenen

11-15 no’lu bileşiklerin yapıları 1H NMR, IR, MS-APCI

ve elementel analiz yöntemleri ile aydınlatılmıştır. Hedef

bileşiklerin (1-15), antimikrobiyal aktiviteleri disk diffüzyon

ve mikrodilüsyon yöntemleri kullanılarak, Gram(+),

Gram(−) bakteri ve mantar standart suşlarına karşı

gerçekleştirilmiştir. Bileşiklerin çözünürlük özelliklerinden

dolayı disk diffüzyon testi ile karşılaştırılabilir sonuçlar

alınamasa da, mikrodilüsyon yöntemi sonuçları bileşiklerin

sadece Enterococcus faecalis üzerinde değişen oranlarda

etkili olduklarını göstermiştir. Elde edilen bilgilerle;

ftalimido, sekonder sülfonamit ve fenil halkasındaki

elektron verici grupların antibakteriyel aktivite için

gerekli olduğu sonucuna varılmıştır. Test edilen bileşikler

arasından, N-fenil-2-ftalimidotaurinamit’in fenil halkasının

para konumundan metil ve metoksi ile sübstitüe edildiği

türevlerin (4, 7), standart

Keywords

Taurinamit, N-sübstitüe-2- ftalimidoetansülfonamit, antibakteriyel, Enterococcus faecalis, mikrodilüsyon

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