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Journals / Turkish Journal of Chemistry / 2010 / Cilt: 34 - Sayı: 3

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
Pages
447–456
Publication Date
2010-03-01
DOI
—
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

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.

📌 3 Key Takeaways

🎯
Objective & Hypothesis: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.
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Key Findings & Data: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).
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Conclusion & Impact: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.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Antimycobacterial and antibacterial activity · DNA gyrase activity · Mannich bases of 3-hydroxy-4H-pyran-4-one.

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 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.

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.

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Cite This Article

US, D., BERK, B., GÜRDAL, E., AYTEKIN, N., KOCAGÖZ, T., ÇAĞLAYAN, B., KURNAZ, İ. A., EROL, D. D. (2010). Mannich base derivatives of 3-hydroxy-6- methyl-4H-pyran-4-one with antimicrobial activity. Turkish Journal of Chemistry, Cilt: 34 - Sayı: 3, 447–456. https://ajindex.com/articles/185274

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References (21)

  1. Katoch, V. M. Indian J. Med. Res. 2004, 120, 290-304.
  2. Wallace, R. J. Jr.; O’Brein, R.; Glassroth, J.; Raleigh, J.; Dutta, A. Am. Rev. Respir. Dis. 1990, 142, 940-953.
  3. Katoch, V. M.; Mohan, K. T. A typical mycobacterial infections. Sharma, S. K., Eds.; Tuberculosis, Jaypee Brothers Medical Publishers (P) Ltd, New Delhi, 2001.
  4. Khan, K.; Wang, J.; Marras, T. K. Am. J. Respir. Crit. Care Med. 2007, 176, 306-313.
  5. Behr, M. A. Microbes Infect. 2008, 10, 968-972.
  6. Kayser, F. H. Medical Microbiology, Georg Thieme Verlag, Stuttgart, 2005.
  7. Besra, G. S.; Chatterjee, D. Lipids and carbohydrates of Mycobacterium tuberculosis; Bloom, B. R., Ed.; Tubercu- losis, ASM Press,
  8. Washington, DC, 1994.
  9. Maxwell, A. Trends Microbiol. 1997,5, 102-109.
  10. Aubry, A.; Fisher, L. M.; Jarlier, V.; Cambau, E. Biochem. Biophys. Res. Commun. 2006, 348, 158-165.
  11. Cole, S. T.; Brosch, R.; Parkhill, J.; Garnier, T.; Churcher, C.; Harris, D.; Gordon, S. V.; Eiglmeier, K.; Gas, S.; Barry, C. E.; Tekaia, F.; Badcock, K.; Basham, D.; Brown, D.; Chillingworth, T.; Connor, R.; Davies, R.; Devlin, K.; Feltwell, T.; Gentles, S.; Hamlin, N.; Holroyd, S.; Hornsby, T.; Jagels, K.; Krogh, A.; McLean, J.; Moule, S.; Murphy, L.; Oliver, K.; Osborne, J.; Quail, M. A.; Rajandream, M. A.; Rogers, J.; Rutter, S.; Seeger; K.; Skelton, J.; Squares, R.; Squares, S.; Sulston, J. E.; Taylor, K.; Whitehead, S.; Barrell, B. G. et al. Nature 1998, 393, 544. Yabuta, T. J. Chem. Soc. 1924, 125, 575-587.
  12. Kayahara, H.; Shibata, N.; Tadasa, K.; Maeda, H.; Kotani, T.; Ichimoto, I. Agric. Biol. Chem. 1990, 54, 2441-2442.
  13. Kotani, T.; Ichimoto, I.; Tatsumi, C.; Fujita, T. Agric. Biol. Chem. 1975, 39, 1311-1317.
  14. Aytemir, M. D.; Hider, R. C.; Erol, D. D.; ¨Ozalp, M.; Ekizo˘glu, M. Turk J. Chem. 2003, 27, 445-452.
  15. Aytemir, M. D.; Erol, D. D.; Hider, R. C.; ¨Ozalp, M. Turk J. Chem. 2003, 27, 757-764.
  16. Wan, H. M.; Chen, C. C.; Giridhar, R.; Chang, T. S.; Wu, W. T. J. Ind. Microbiol. Biotechnol. 2005, 32, 227-233.
  17. Yamato, M.; Yasumoto, Y.; Sakai, J.; Luduena, R. F.; Baneerjee, A.; Tashiro, T. J. Med. Chem. 1987, 30, 1897 Tamura, T.; Mitsumori, K.; Totsuka, Y.; Wakabayashi, K.; Kido, R.; Kasai, H.; Nasu, M.; Hirose, M. Toxicology, 222, 213-224.
  18. Aytemir, M. D.; C¸ alı¸s, ¨U.; ¨Ozalp, M. Arch. Pharm. Pharm. Med. Chem. 2004, 337, 281-288.
  19. Aytemir, M. D.; C¸ alı¸s, ¨U. Hacettepe University Journal of the Faculty of Pharmacy 2007, 27, 1-10.
  20. Aytemir, M. D.; C¸ alı¸s, ¨U. FABAD J. Pharm. Sci. 2006, 31, 23-29.
  21. Kim, H.; Choi, J.; Cho, J. K.; Kim, S