Synthesis, Molecular Docking, DFT and Antimicrobial Activity Studies of 2-(p-Fluorophenyl)-5-(2-(4- acetylpiperazin-1-yl)acetamido)benzoxazole

Abstract

In this study, the new compound 2-(p-Fluorophenyl)-5-(2-(4-acetylpiperazine-1-yl) acetamido)benzoxazole was synthesized in three steps and its structure was clarified by 1H-NMR and 13C-NMR spectroscopy. Its antimicrobial activity was studied on Staphylococcus aureus ATCC 29213, Enterococcus faecalis ATCC 29212, Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853, Acinetobacter baumannii NTCC 13304, Klebsiella pneumoniae ATCC 700603, Candida albicans ATCC 1023, and their isolates. When the antimicrobial activity results were examined, although the reference drugs showed better antimicrobial activity in general, the synthesized compound showed quite promising activity on E. faecalis isolates and E. coli isolates compared to ampicillin with MIC: 32 µg mL-1. Molecular docking study was carried out on the DNA gyrase subunit B structure. Theoretical ADME (absorption, distribution, metabolism, elimination) properties were calculated. In addition, HOMO-LUMO energies, molecular electrostatic potential analysis, and optimized geometric structure were determined using the DFT/B3LYP method and the 6-311G (d,p) basis set, and the results were displayed.

Keywords

• Benzoxazole
• antimicrobial activity
• DFT
• molecular docking

2-(p-Florofenil)-5-(2-(4-asetilpiperazin-1-il)asetamido)benzoksazol’ün Sentezi, Moleküler Doking, DFT ve Antimikrobiyal Aktivite Çalışmaları

Abstract

Bu çalışmada, yeni 2-(p-Florofenil)-5-(2-(4-asetilpiperazin-1-il)asetamido)benzoksazol bileşiği üç aşamada sentezlenmiş ve yapısı 1H-NMR ve 13C-NMR spektroskopisi ile aydınlatılmıştır. Antimikrobiyal aktivite çalışmaları, Staphylococcus aureus ATCC 29213, Enterococcus faecalis ATCC 29212, Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 27853, Acinetobacter baumannii NTCC 13304, Klebsiella pneumoniae ATCC 700603, Candida albicans ATCC 10231 ve bunların izolatları izolatları üzerinde gerçekleştirildi. Antimikrobiyal aktivite sonuçlarına göre, referans ilaçlar genel olarak daha iyi antimikrobiyal aktivite göstermesine rağmen sentezlenen bileşik, MİK: 32 µg mL-1 ile ampisilin ile karşılaştırıldığında E. faecalis izolatları ve E. coli izolatları üzerinde oldukça umut verici aktivite gösterdi. Moleküler doking çalışması DNA giraz subunit B yapısı üzerinde gerçekleştirildi. Teorik ADME (absorbsiyon, dağılım, metabolizma, eliminasyon) özellikleri hesaplandı. Ayrıca DFT/B3LYP yöntemi ve 6-311G (d,p) temel seti kullanılarak HOMO-LUMO enerjileri, moleküler elektrostatik potansiyel analizi ve optimize edilmiş geometrik yapısı belirlendi ve sonuçlar görüntülendi.

Keywords

• Benzoksazol
• antimikrobiyal aktivite
• DFT
• moleküler doking

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