Mannich base derivatives of 3-hydroxy-6- methyl-4H-pyran-4-one with antimicrobial activity

Authors

DEMET US
BARKIN BERK
ENİSE ECE GÜRDAL
NİHAN AYTEKİN
ZÜHTÜ TANIL KOCAGÖZ
BERRAK ÇAĞLAYAN
IŞIL KURNAZ
DİLEK DEMİR EROL

DOI

10.3906/kim-0908-214

Abstract

A series of 3-hydroxy-6-methyl-2-[(substitutedpiperidine-1-yl) methyl]-4H-pyran-4-one structured compounds were synthesized by reacting 5-hydroxy-2-methyl-4H-pyran-4-one with suitable piperidine derivatives using Mannich reaction conditions. Antibacterial activities of the compounds for E. coli ATCC 25922, S. paratyphi ATCC BAA-1250, S. flexneri ATCC 12022, E. gergoviae ATCC 33426, and M. smegmatis ATCC 14468 were assessed in vitro by the broth dilution method for determination of minimum inhibitory concentration (MIC). In addition, their inhibitory effects over DNA gyrase enzyme were evaluated using a DNA gyrase supercoiling assay. All the synthesized compounds showed a MIC value of either 8 or 16 \mu g/mL for M. smegmatis, whereas minimum to moderate activity was achieved for the others. 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 to treat non-tuberculous mycobacterial infections.

Keywords

Antimycobacterial and antibacterial activity; DNA gyrase activity; Mannich bases of 3-hydroxy-4H-pyran-4-one.

First Page

447

Last Page

456

Recommended Citation

US, DEMET; BERK, BARKIN; GÜRDAL, ENİSE ECE; AYTEKİN, NİHAN; KOCAGÖZ, ZÜHTÜ TANIL; ÇAĞLAYAN, BERRAK; KURNAZ, IŞIL; and EROL, DİLEK DEMİR (2010) "Mannich base derivatives of 3-hydroxy-6- methyl-4H-pyran-4-one with antimicrobial activity," Turkish Journal of Chemistry: Vol. 34: No. 3, Article 14. https://doi.org/10.3906/kim-0908-214
Available at: https://journals.tubitak.gov.tr/chem/vol34/iss3/14