Synthesis of Some New Benzoxazole Derivatives and Antimicrobial and Cytotoxic Activity Studies

Year 2021, Issue: 21, 455 - 462, 31.01.2021

Meryem Erol , İsmail Çelik , Gülcan Kuyucuklu , Ebru Uzunhisarcıklı

https://doi.org/10.31590/ejosat.822417

Cited By: 1

Abstract

There is an urgent need to develop new antimicrobial drugs due to the rapid development of resistance to increasing microbial infectious diseases and drugs used in their treatment. Also, the compounds synthesized for use in cancer treatment limit their use due to their cytotoxic effect on normal cells and cancerous cells, and their side effects are high. For this reason, researches continue to intensify the drugs developed for cancer treatment to be selectively effective on cancer cells and to reduce their side effects as much as possible. Within this study's scope, 7 compounds of 2-(p-substituted phenyl)-5-(2-substitutedacetamido) were synthesized in 3 steps, 2 of which were original, and their structures were illuminated by HRMS, 1H-NMR, and 13C-NMR spectroscopy methods. Antimicrobial effects on 10 different microorganisms were evaluated. In addition, cytotoxic activities were investigated on MCF-7 and A549 cell lines by the MTT method. As a result of the study, it was determined that the synthesized compounds were both antibacterial and antifungal at MIC values ranging from 64-256 µg/mL, and compound 7 had significant cytotoxic activity on both A549 and MCF-7. The results obtained will make an important contribution to the studies conducted to develop new or alternative antimicrobial and cytotoxic agents.

Keywords

Benzoxazole, Synthesis, Antimicrobial activity, Cytotoxicity, ADME prediction

Supporting Institution

Erciyes University Scientific Research Projects Coordination Unit

Project Number

THD-2020-10038

Thanks

This work has been supported by Erciyes University Scientific Research Projects Coordination Unit with research project THD-2020-10038. NMR analysis of the compounds were performed by Erciyes University Technology and Research Center (TAUM) and HRMS analysis were performed by Bilkent University National Nanotechnology Research Center (UNAM).

Bazı Yeni Benzoksazol Türevlerinin Sentezi ve Antimikrobiyal ve Sitotoksik Aktivite Çalışmaları

Abstract

Artan mikrobiyal enfeksiyon hastalıklara ve bunların tedavisinde kullanılan ilaçlara karşı hızla direnç gelişmesi nedeniyle yeni antimikrobiyal ilaçların geliştirilmesine acil ihtiyaç duyulmaktadır. Ayrıca kanser tedavisinde kullanmak amacıyla sentezlenen bileşiklerin kanserli hücrelerde olduğu kadar normal hücrelerde de sitotoksik etki göstermesi ve yan etkilerinin fazla olması nedeniyle kullanımını sınırlı hale getirmektedir. Bu nedenle kanser tedavisi için geliştirilen ilaçların seçici olarak kanserli hücreler üzerinde etkili olması ve yan etkilerinin mümkün olduğunca azaltılması yönünde araştırmalar yoğun olarak devam etmektedir. Bu çalışma kapsamında 2'si orjinal olmayan 7 tane 2-(p-substitutedphenyl)-5-(2-substitutedacetamido) bileşiğinin 3 basamakta sentezi gerçekleştirildi, yapıları HRMS, 1H-NMR ve 13C-NMR spektrokpisi yöntemleri ile aydınlatıldı. 10 farklı mikroorganizma üzerinde antimikrobiyal etkileri değerlendirildi. Ayrıca MCF-7 ve A549 hüzre hatları üzerinde MTT metodu ile sitotoksik aktiviteleri araştırıldı. Çalışma sonucunda sentezlenen bileşiklerin 64-256 µg/mL arasında değişen MİK değerlerinde hem antibakteriyel hem de antifungal etkili oldukarı belirlenmiş ve bileşik 7'nin hem A549 hem de MCF-7 üzerinde önemli sitotoksik aktivitesi bulunmuştur. Elde edilen sonuçlar yeni veya alternatif ilaç antimikrobiyal ve sitotoksik ajan geliştirmek için yapılan çalışmalara önemli bir katkı sağlayacaktır.

Keywords

Benzoksazol, sentez, Antimikrobiyal aktivite, Sitotoksisite, ADME tahmini

Project Number

THD-2020-10038

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