4H-Pyran-4-one derivatives:; leading molecule for preparation of compounds with antimycobacterial potential

Authors

DEMET US
ECE GÜRDAL
BARKIN BERK
SİNEM ÖKTEM
TANIL KOCAGÖZ
BERRAK ÇAĞLAYAN
IŞIL AKSAN KURNAZ
DİLEK DEMİR EROL

DOI

10.3906/kim-0905-15

Abstract

A series of 3-hydroxy-6-methyl-2-((4-substitutedpiperazin-1- yl)methyl)-4H-pyran-4-one structured compounds were synthesized by reacting 5-hydroxy-2-methyl-4H-pyran-4-one with suitable piperazine derivatives using Mannich reaction conditions. Antibacterial activities of the compounds for E. coli, S. paratyphi, S. flexneri, E. gergoviae, and M. smegmatis were assessed in vitro by using broth dilution for determination of the minimum inhibitory concentration (MIC). In addition, their inhibitory effects over DNA gyrase enzyme were evaluated using a DNA gyrase supercoiling assay. Among the synthesized compounds; compound 7 showed a 4 \mu g/mL MIC value for M. smegmatis, whereas the other compounds demonstrated moderate to high activity. Those tested in the supercoiling assay had at best a very mild inhibition of the enzyme. This series deserves further attention for testing over Mycobacterium species and topoisomerase II inhibition to develop new lead drugs.

Keywords

Antimycobacterial activity; DNA gyrase activity; hydroxy-4H-pyran-4-one.

First Page

803

Last Page

812

Recommended Citation

US, DEMET; GÜRDAL, ECE; BERK, BARKIN; ÖKTEM, SİNEM; KOCAGÖZ, TANIL; ÇAĞLAYAN, BERRAK; KURNAZ, IŞIL AKSAN; and EROL, DİLEK DEMİR (2009) "4H-Pyran-4-one derivatives:; leading molecule for preparation of compounds with antimycobacterial potential," Turkish Journal of Chemistry: Vol. 33: No. 6, Article 9. https://doi.org/10.3906/kim-0905-15
Available at: https://journals.tubitak.gov.tr/chem/vol33/iss6/9