Synthesis of New Azoquinolone: Evaluation of Structural, Spectral Properties, and Antimicrobial Activity

Öznur Ölmez Nalcıoğlu; Mehtap Yakut; Ayşe Gül Caniklioğlu

doi:10.18596/jotcsa.1719222

Synthesis of New Azoquinolone: Evaluation of Structural, Spectral Properties, and Antimicrobial Activity

Abstract

A new azo dye containing quinolone (QANB) was synthesized by the ring-opening of pyranoquinolone (PQ), which was obtained from N-ethyl aniline and diethyl malonate. Surprisingly, we determined that under strong base conditions, azo coupling occurred at the 8-position of the quinolone group rather than at the 3-position of the pyroquinolone ring. Structure of 3-[1-ethyl-4-hydroxy-8-(4-nitro-phenylazo)-2-oxo-1,2-dihydro-quinolin-3-yl]-3-hydroxy-acrylic acid (QANB) was elucidated by 1H NMR, 13C NMR, 13C NMR DEPT, 13C NMR APT, 2D NMR (1H-1H COSY and 1H-13C HMQC) and HRMS Analyses. Moreover, we investigated the antimicrobial activity of QANB on eight different bacteria and two different yeasts. The disc diffusion method and the minimum inhibitory concentration value determination (MIC) were used for antimicrobial activity. QANB demonstrated broad-spectrum antibacterial activity against both Gram-positive and Gram-negative bacteria. However, it has effectively shown activity against E. aerogenes, which causes pneumonia, sepsis, urinary tract infections, and wound infections. QANB also showed significant activity against C. albicans. The fact that QANB is much more effective against C. albicans than nystatin, which is widely used as an antifungal drug, supports the idea that this compound can be used as a potential antifungal drug.

Keywords

Thanks

The authors are grateful to Giresun University Central Research Laboratory (GRUMLAB) for technical support and Giresun University Biology Department for technical support during antimicrobial study.

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Details

Primary Language

English

Subjects

Natural Products and Bioactive Compounds, Organic Chemical Synthesis

Journal Section

Research Article

Authors

Öznur Ölmez Nalcıoğlu ^*
0000-0002-9813-1572
Türkiye

Mehtap Yakut
0000-0002-6237-8522
Türkiye

Ayşe Gül Caniklioğlu
0000-0003-0043-6624
Türkiye

Publication Date

December 1, 2025

Submission Date

June 13, 2025

Acceptance Date

September 25, 2025

Published in Issue

Year 2025 Volume: 12 Number: 4

DOI

https://doi.org/10.18596/jotcsa.1719222

IZ

https://izlik.org/JA37JT77MZ

Cite

RIS / Bibtex

APA

Ölmez Nalcıoğlu, Ö., Yakut, M., & Caniklioğlu, A. G. (2025). Synthesis of New Azoquinolone: Evaluation of Structural, Spectral Properties, and Antimicrobial Activity. Journal of the Turkish Chemical Society Section A: Chemistry, 12(4), 197-206. https://doi.org/10.18596/jotcsa.1719222

AMA

1.Ölmez Nalcıoğlu Ö, Yakut M, Caniklioğlu AG. Synthesis of New Azoquinolone: Evaluation of Structural, Spectral Properties, and Antimicrobial Activity. JOTCSA. 2025;12(4):197-206. doi:10.18596/jotcsa.1719222

Chicago

Ölmez Nalcıoğlu, Öznur, Mehtap Yakut, and Ayşe Gül Caniklioğlu. 2025. “Synthesis of New Azoquinolone: Evaluation of Structural, Spectral Properties, and Antimicrobial Activity”. Journal of the Turkish Chemical Society Section A: Chemistry 12 (4): 197-206. https://doi.org/10.18596/jotcsa.1719222.

EndNote

Ölmez Nalcıoğlu Ö, Yakut M, Caniklioğlu AG (December 1, 2025) Synthesis of New Azoquinolone: Evaluation of Structural, Spectral Properties, and Antimicrobial Activity. Journal of the Turkish Chemical Society Section A: Chemistry 12 4 197–206.

IEEE

[1]Ö. Ölmez Nalcıoğlu, M. Yakut, and A. G. Caniklioğlu, “Synthesis of New Azoquinolone: Evaluation of Structural, Spectral Properties, and Antimicrobial Activity”, JOTCSA, vol. 12, no. 4, pp. 197–206, Dec. 2025, doi: 10.18596/jotcsa.1719222.

ISNAD

Ölmez Nalcıoğlu, Öznur - Yakut, Mehtap - Caniklioğlu, Ayşe Gül. “Synthesis of New Azoquinolone: Evaluation of Structural, Spectral Properties, and Antimicrobial Activity”. Journal of the Turkish Chemical Society Section A: Chemistry 12/4 (December 1, 2025): 197-206. https://doi.org/10.18596/jotcsa.1719222.

JAMA

1.Ölmez Nalcıoğlu Ö, Yakut M, Caniklioğlu AG. Synthesis of New Azoquinolone: Evaluation of Structural, Spectral Properties, and Antimicrobial Activity. JOTCSA. 2025;12:197–206.

MLA

Ölmez Nalcıoğlu, Öznur, et al. “Synthesis of New Azoquinolone: Evaluation of Structural, Spectral Properties, and Antimicrobial Activity”. Journal of the Turkish Chemical Society Section A: Chemistry, vol. 12, no. 4, Dec. 2025, pp. 197-06, doi:10.18596/jotcsa.1719222.

Vancouver

1.Öznur Ölmez Nalcıoğlu, Mehtap Yakut, Ayşe Gül Caniklioğlu. Synthesis of New Azoquinolone: Evaluation of Structural, Spectral Properties, and Antimicrobial Activity. JOTCSA. 2025 Dec. 1;12(4):197-206. doi:10.18596/jotcsa.1719222