Novel 3-(2-Oxo-2H-benzo[b][1,4]oxazin-3-yl)propanoates from Dimethyl-2-oxoglutarate and Test of Their Biological Activity
Kamel Hachama
Laboratoire de Recherche Plantes Médicinales et Aromatiques, Département de Chimie Industrielle, Université Saâd Dahlab de Blida, 09000 Blida, B. P. 270, Algeria
Search for more papers by this authorCorresponding Author
Mohamed Khodja
Laboratoire de Recherche Plantes Médicinales et Aromatiques, Département de Chimie Industrielle, Université Saâd Dahlab de Blida, 09000 Blida, B. P. 270, Algeria
E-mail: [email protected]Search for more papers by this authorSaad Moulay
Laboratoire Chimie-Physique Moléculaire et Macromoléculaire, Département de Chimie Industrielle, Université Saâd Dahlab de Blida, 09000 Blida, B. P. 270, Algeria
Search for more papers by this authorHocine Boutoumi
Laboratoire de Recherche Plantes Médicinales et Aromatiques, Département de Chimie Industrielle, Université Saâd Dahlab de Blida, 09000 Blida, B. P. 270, Algeria
Search for more papers by this authorLothar Hennig
Institut für Organische Chemie der Universität Leipzig, Johannisallee 29, D-04103 Leipzig, Germany
Search for more papers by this authorDieter Sicker
Institut für Organische Chemie der Universität Leipzig, Johannisallee 29, D-04103 Leipzig, Germany
Search for more papers by this authorKamel Hachama
Laboratoire de Recherche Plantes Médicinales et Aromatiques, Département de Chimie Industrielle, Université Saâd Dahlab de Blida, 09000 Blida, B. P. 270, Algeria
Search for more papers by this authorCorresponding Author
Mohamed Khodja
Laboratoire de Recherche Plantes Médicinales et Aromatiques, Département de Chimie Industrielle, Université Saâd Dahlab de Blida, 09000 Blida, B. P. 270, Algeria
E-mail: [email protected]Search for more papers by this authorSaad Moulay
Laboratoire Chimie-Physique Moléculaire et Macromoléculaire, Département de Chimie Industrielle, Université Saâd Dahlab de Blida, 09000 Blida, B. P. 270, Algeria
Search for more papers by this authorHocine Boutoumi
Laboratoire de Recherche Plantes Médicinales et Aromatiques, Département de Chimie Industrielle, Université Saâd Dahlab de Blida, 09000 Blida, B. P. 270, Algeria
Search for more papers by this authorLothar Hennig
Institut für Organische Chemie der Universität Leipzig, Johannisallee 29, D-04103 Leipzig, Germany
Search for more papers by this authorDieter Sicker
Institut für Organische Chemie der Universität Leipzig, Johannisallee 29, D-04103 Leipzig, Germany
Search for more papers by this authorAbstract
Five novel 3-(2-oxo-2H-benzo[b][1,4]oxazin-3-yl)propanoates were synthesized under mild conditions from 2-aminophenols and dimethyl-2-oxoglutarate. Biological assays of these 1,4-benzoxazinones were conducted with three bacterial strains and one yeast. All compounds were active against a Candida albicans ATCC 10231, whereas only methyl 3-(6-methyl-2-oxo-2H-benzo[b][1,4]oxazin-3-yl)propanoate showed a general moderate activity against the bacterial strains tested.
REFERENCES AND NOTES
- 1 Stottmeister, U.; Aurich, A.; Wilde, H.; Andersch, J.; Schmidt, S.; Sicker, D. J. Industr Microbiol & Biotechnol 2005, 32, 651.
- 2 Ilchenko, P.; Lysyanskaya, V. Y.; Finogenova, T. V.; Morgunov, I. G. Microbiology 2010, 79, 450.
- 3 Zhou, J.; Zhou, H.; Di, G.; Liu, L.; Chen, J. Lett Appl Microbiol 2011, 51, 264.
- 4 Holz, M.; Otto, C.; Kretzschmar, A.; Yovkova, Y.; Aurich, A.; Pötter, M.; Marx, A.; Barth, G. Appl Microbiol Biotechnol 2011, 89, 1519.
- 5 Blitzke, T.; Sicker, D.; Wilde, H. J Heterocycl Chem 1997, 34, 453.
- 6 Sicker, D.; Schulz, M. In Studies in Natural Product Chemistry; , Ed.; Elsevier, Amsterdam, 2002, Vol 27 (Bioactive Natural Products – Part H), pp 185–232.
- 7 Hassan, G. S. Egypt J Pharm Sci 2004, 18, 129.
- 8 Bredenberg, J. B. S.; Honkanen, E., Virtanen, A. I. Acta Chem Scand 1962, 16, 135.
- 9
Benzatti, C.;
Heidemoergher, F.;
Melloni, P. J Heterocycl Chem 1983, 20, 259.
10.1002/jhet.5570200201 Google Scholar
- 10 Hagen, S. R.; Thompson, J. D. J Chromatogr A 1995, 692, 167.
- 11 Shimada, K.; Mitamura, K.; Ishitoya, S.; Hirakata, K. Japan J Liquid Chromatogr 1993, 16, 3965.
- 12 Suzanne, F.-F.; Le Bris, M. T.; Guette, J. P.; Valeur, B. J Phys Chem 1988, 92, 6233.
- 13 Azuma, K.; Suzuki, S.; Uchiyama, S.; Kajiro, T.; Santa, T.; Imai, K. Photochem Photobiol Sci 2003, 2, 443.
- 14 Biekert, E.; Hoffmann, D.; Meyer, F. J. Chem Ber 1961, 94, 1664.
- 15 Weidinger, H.; Kranz, J. Chem Ber 1964, 97, 1599.
- 16 Orphanos, D. G.; Taurins, A. Can J Chem 1966, 44, 1795.
- 17 Moffett, R. B. J Med Chem 1966, 9, 475.
- 18 Yavari, I.; Souri, S.; Sirouspour, M.; Djahaniani, H. Synthesis 2006, 19, 3243.
- 19 Ballini, R.; Palmieri, A.; Talaq, M. A.; Gabrielli, S. Adv Synth Catal 2009, 351, 2611.
- 20 Hartenstein, H.; Blitzke, T.; Sicker, D.; Wilde, H. J Prakt Chem 1993, 335, 176.
- 21 Balows, A.; Hausler, W. J.; Herrmann, K. L.; Isenberg, H. D.; Shadomy, H. J. Manual of Clinical Microbiology; American Society for Microbiology: Washington, DC, 1991; 5th ed.; pp. 360–477.
- 22 Gein, V. L.; Rassudikhina, N. A.; Shepelina, N. V.; Vakhrin, M. I.; Babuschkina, E. B.; Voronina, E. V. Pharm J Chem 2008, 42, 529.
- 23 Hofmann, D.; Knop, M.; Hao, H.; Hennig, L.; Sicker, D.; Schulz, M. J Nat Prod 2006, 69, 34.
- 24 Bauer, A. W.; Kirby, W. M.; Sherris, J. C.; Turck, M. Am J Clin Pathol 1966, 45, 493.
- 25 Cavallo, J. D.; Chardon, H.; Chidiac, C.; Choutet, P.; Courvalin, P.; Dabernat, H.; Drugeon, H.; Dubreuil, L.; Goldstein, F.; Jarvalier, V.; Leclercq, R.; Nicolas-Chanoine, M. H.; Philipon, A.; Quentin, C.; Rouveix, B.; Sirot, J.; Soussy, C. J. Communiqué du Comité de l'Antibiogramme; Société Française de Microbiologie; Edition de Janvier; Créteil Cedex, 2006.
