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

Us D., Gurdal E., Berk B., Oktem S., Kocagoz T., Caglayan B., ...Daha Fazla

Turkish Journal of Chemistry, cilt.33, sa.6, ss.803-812, 2009 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 33 Sayı: 6
  • Basım Tarihi: 2009
  • Doi Numarası: 10.3906/kim-0905-15
  • Dergi Adı: Turkish Journal of Chemistry
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Sayfa Sayıları: ss.803-812
  • Anahtar Kelimeler: Antimycobacterial activity, DNA gyrase activity, hydroxy-4H-pyran-4-one, KOJIC ACID, IRON CHELATORS, TYROSINASE
  • Acıbadem Mehmet Ali Aydınlar Üniversitesi Adresli: Evet

Özet

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.