The Synthesis and Antimicrobial Activity of \\\g-Butyrolactone Derivatives

This paper examines the synthesis of g-butyrolactone compounds 2, 3, 4, 5, and 9, and their potential antimicrobial nature and ability. The structures of all the compounds mentioned above were determined and confirmed with elemental analyses, and IR, 1H-NMR, and 13C-NMR spectroscopy. The in vitro antimicrobial activity of compounds 2, 3, 4, 5, and 9 was examined and evaluated against the following pathogens: Enterobacter aerogenes, Enterobacter cloacae, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus agalactiae, Aspergillus niger, and Candida albicans. Compound 5 (20 mg/mL) demonstrated high antimicrobial activity against S. epidermidis, which was closely comparable to the antimicrobial activity of streptomycin.

The Synthesis and Antimicrobial Activity of \\\g-Butyrolactone Derivatives

This paper examines the synthesis of g-butyrolactone compounds 2, 3, 4, 5, and 9, and their potential antimicrobial nature and ability. The structures of all the compounds mentioned above were determined and confirmed with elemental analyses, and IR, 1H-NMR, and 13C-NMR spectroscopy. The in vitro antimicrobial activity of compounds 2, 3, 4, 5, and 9 was examined and evaluated against the following pathogens: Enterobacter aerogenes, Enterobacter cloacae, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus agalactiae, Aspergillus niger, and Candida albicans. Compound 5 (20 mg/mL) demonstrated high antimicrobial activity against S. epidermidis, which was closely comparable to the antimicrobial activity of streptomycin.

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Hoffmann, H. M. R.; Rabe, J. Angew Chem. 1985, 24, 94-110.

Devon; T. K.; Scott, A. I. Handbook of Naturally Occurring Compounds, Academic Press, New York, Vol. 1, pp 249-250, 1975.

Yang, X.; Shimizu, Y.; Steiner, J. R.; Clardy, J. Tetrahedron Lett. 1993, 34, 761.

Davidson, B. S.; Ireland, C. M. J. Nat. Prod. 1990, 53, 1036.

Kazlauskas, R.; Murphy, P. T.; Quinn, R. J.; Wells, R. J. Tetrahedron Lett. 1977, 18, 37.

Pettus, J. A. Jr.; Wing, R. M.; Sims, J. J. Tetrahedron Lett. 1977, 18, 41.

Hung, T. V.; Mooney, B. A.; Prager, R. H.; Tippett, J. M. Aus. J. Chem. 1981, 34, 383-395.

Gammill, R. B.; Wilson, C. A.; Bryson, T. A. Synth. Commun. 1975, 5, 245-251.

Grieco, P. A. Synthesis 1975, 67-82.

Grieco, P. A.; Noguesz, J.A; Masaki, Y.; Hiroi, K.; Nishizawa, I. J. Med. Chem. 1977, 20, 71-76.

Huang, S.; Piantadosi, C.; Pagano, J. S.; Geissman, T. A.; Lee, K. H. Cancer. Res. 1971, 31, 1649-1656. Rao, Y. S. Chem. Rev. 1976, 76, 625-694.

Pelter, A.; Satyanarayana, P.; Ward, R. S. Tetrahedron Lett. 1981, 22, 1549-1550.

Geissman, T. A.; Irwin, M. A. Pure and Appl. Chem. 1970, 21, 167-180.

Howie, G. A.; Stamos I. K.; Cassady, J. M. J. Med. Chem. 1976, 19, 309-313.

Kupchan, S. M.; Earkin, M. A.; Thomas, A. M. J. Med. Chem. 1971, 14, 1147-1152.

Askin, D.; Wallace, M. A.; Vacca, J. P.; Reamer, R. A.; Volante, R. P.; Shinkai, I. J. Org. Chem. 1992, 57, 2773.

Chamberlain, R.; Koch, C. J. Org. Chem. 1993, 58, 2725-2737 and references therein.

Lee, K.; Choi, Y.; Gullen, S.; Wirtz, S. S.; Schinazi, R. F.; Cheng, Y. C.; Chu, C. K. J. Med. Chem. 1999, 42, 1328.

Garcıa, C.; Martin T.; Martin, V. S. J. Org. Chem. 2001, 66, 1420-1428.

DEPT13C NMR: Quaternary carbons are not observed, while others are positive, negative, or null depending on the “angle” (45, 90, 135) used in the experiment. This technique effectively identiŞes the most basic ◦ ◦ ◦ structural units: C, CH, CH2, and CH3. Kavanagh, F. Analytical microbiology, Acad. Press, New York, 1972.

NCCLS, Performance Standards for Antimicrobial Disk Susceptibility Tests. Approved Standard NCCLS Publication M2/A4, Villanova, PA, USA, 1990.

Bhalerao, U. T.; Rapopart, H. J. Am. Chem. Soc. 1971, 93, 4835-4940.

Solujic, S.; Sukdolak S.; Ratkovic, Z. Tetrahedron Lett. 1991, 32, 4577-4578.

Shoppee, C. W.; Krueger, G. J. Chem. Soc. 1961, 3641-3655.

Conley, R. T.; Longe, R. J. J. Org. Chem. 1963, 28, 210-214.

Oka, K.; Hore, S. J. Org. Chem. 1978, 43, 3790-3791.

Suginome, H.; Kaji M.; Yamada, S. J. Chem. Soc., Perkin Trans. 1988, 1, 321-326.

Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
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