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

Demet US; Barkın BERK; Ece GÜRDAL; Nihan AYTEKIN; Tanıl KOCAGÖZ; Berrak ÇAĞLAYAN; İşıl AKSAN KURNAZ; Dilek DEMİR EROL

Makale detayları

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

Yazarlar:

Demet US | Barkın BERK | Ece GÜRDAL | Nihan AYTEKIN | Tanıl KOCAGÖZ | Berrak ÇAĞLAYAN | İşıl AKSAN KURNAZ | Dilek DEMİR EROL

Yayıncı:

TUBITAK

Dergi:

Turkish Journal of Chemistry 2010 Vol.34 Issue 3, pp.447-456

Belge Tipi:

Makale

Yayın Tarihi:

2/2010

Belge Dili:

Türkçe

Document ID (Org No.):

2000728069

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527

Özet:

 

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 m 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.

 

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 m 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.

Makale detayları

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

Yazarlar: Demet US | Barkın BERK | Ece GÜRDAL | Nihan AYTEKIN | Tanıl KOCAGÖZ | Berrak ÇAĞLAYAN | İşıl AKSAN KURNAZ | Dilek DEMİR EROL

Yayıncı: TUBITAK

Dergi: Turkish Journal of Chemistry 2010 Vol.34 Issue 3, pp.447-456

Belge Tipi: Makale

Yayın Tarihi: 2/2010

Belge Dili: Türkçe

Document ID (Org No.): 2000728069

Sıklık: İki Aylık

eISSN: 1303-6130

pISSN: 1300-0527

Sayı

Yazarlar:

Demet US | Barkın BERK | Ece GÜRDAL | Nihan AYTEKIN | Tanıl KOCAGÖZ | Berrak ÇAĞLAYAN | İşıl AKSAN KURNAZ | Dilek DEMİR EROL

Yayıncı:

TUBITAK

Dergi:

Turkish Journal of Chemistry 2010 Vol.34 Issue 3, pp.447-456

Belge Tipi:

Makale

Yayın Tarihi:

2/2010

Belge Dili:

Türkçe

Document ID (Org No.):

2000728069

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527