Synthesis, Structural Characterization, and Biological Evaluation of a Novel Benzothiazole Schiff Base

Yıl 2025, Cilt: 7 Sayı: 3, 282 - 291, 30.09.2025

İrem Akyol , Neslihan Güleç , Mustafa Yıldız

https://doi.org/10.51435/turkjac.1726252

Öz

: In this study, we investigated the biological activity of a new benzothiazolimine compound, 4-methoxy-2-[(6-methoxybenzo[d]thiazol-2-amine)methyl]phenol, which was synthesized from the reaction of 6-methoxybenzo[d]thiazol-2-amine and 2-hydroxy-5-methoxybenzaldehyde. The chemical structure of the compound was elucidated by various spectroscopic techniques. The antimicrobial activity was evaluated by assessing the minimum inhibitory concentrations against several bacterial and yeast strains, revealing significant effectiveness against yeasts. DNA binding studies demonstrated that the compound interacts with DNA electrostatically. Agarose gel electrophoresis further confirmed that the compound induces oxidative DNA cleavage. The antimutagenicity of the compound was evaluated using the Ames/Salmonella test, showing a high inhibition rate of base-pair mutations. These results suggest that the compound possesses notable biological activity and warrants further investigation.

Anahtar Kelimeler

6-Methoxybenzo[d]thiazol-2-amine , Spectroscopy , Antimicrobial activity , DNA cleavage , DNA binding , Antimutagenicity

Yeni Bir Benzotiyazol Schiff Bazının Sentezi, Yapısal Karakterizasyonu ve Biyolojik Değerlendirmesi

Öz

Bu çalışmada, 6-metoksibenzo[d]tiazol-2-amin ile 2-hidroksi-5-metoksibenzaldehid reaksiyonundan sentezlenen yeni bir benzotiyazolimin bileşiği olan 4-metoksi-2-[(6-metoksibenzo[d]tiyazol-2-amin)metil]fenolün biyolojik aktivitesi incelenmiştir. Bileşiğin kimyasal yapısı çeşitli spektroskopik tekniklerle aydınlatılmıştır. Antimikrobiyal aktivite, farklı bakteri ve maya suşlarına karşı minimum inhibisyon konsantrasyonları belirlenerek değerlendirilmiş ve mayalara karşı anlamlı etkinlik göstermiştir. DNA bağlanma çalışmaları, bileşiğin DNA ile elektrostatik etkileşim yoluyla bağlandığını ortaya koymuştur. Agaroz jel elektroforezi, bileşiğin oksidatif DNA kırılmasına neden olduğunu doğrulamıştır. Ames/Salmonella testi kullanılarak yapılan antimutajenite değerlendirmesinde ise baz çifti mutasyonlarına karşı yüksek oranda inhibisyon gözlenmiştir. Bu bulgular, söz konusu bileşiğin kayda değer biyolojik aktiviteye sahip olduğunu ve daha ileri çalışmaların gerekliliğini göstermektedir.

Anahtar Kelimeler

6-Metoksibenzo[d]tiyazol-2-amin , Spektroskopi , Antimikrobiyal aktivite , DNA kırma , DNA bağlanma , Antimutajenite

Kaynakça

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