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Novel and Efficient Synthesis of Tetrazolo[1,5-b]-1,2,5-oxadiazepines as Antibacterial Activities from Ethyl 1-aminotetrazole-5-carboxylate

  • El-Badry, Susan M. ;
  • Taha, Mamdouh A.M.
  • Received : 2011.07.02
  • Accepted : 2011.09.06
  • Published : 2011.12.20

Abstract

Ethyl 1-aminotetrazole-5-carboxylate (1) has been utilized to construct a variety of novel tetrazolo [1,5-b]-1,2,5-oxadiazepine derivatives which repesent a relatively little explored group with interesting antibacterial activities. The synthesized compounds were elucidated using IR, $^1H$ NMR and mass spectroscopic methods, besides elemental analyses.

Keywords

Ethyl 1-aminotetrazole-5-carboxylate;Tetrazolo[1,5-b]-1,2,5-oxadiazepines;Antibacterial activities

References

  1. Taha, M. A. M.; El-Badry, S. M. J. Korean Chem. Soc. 2010, 54, 414. https://doi.org/10.5012/jkcs.2010.54.4.414
  2. Taha, M. A. M.; El-Badry, S. M. Monatsh. Chem. 2008, 139, 1261. https://doi.org/10.1007/s00706-008-0902-8
  3. Taha, M. A. M. Phosphorus, Sulphur, Silicon Relat. Elem. 2008, 183, 2525. https://doi.org/10.1080/10426500801967773
  4. Taha, M. A. M. Monatsh. Chem. 2007, 138, 505. https://doi.org/10.1007/s00706-007-0599-0
  5. Taha, M. A. M.; El-Badry, S. M. Phosphorus, Sulfur, Silicon Relat. Elem. 2007, 182, 1011. https://doi.org/10.1080/10426500601090768
  6. Taha, M. A. M.; El-Badry, S. M. J. Chinese Chem. Soc. 2006, 53, 1181.
  7. Taha, M. A. M. J. Chinese Chem. Soc. 2005, 52, 137.
  8. Moderhack, D. J. Prakt. Chem. 1998, 340, 687. https://doi.org/10.1002/prac.19983400802
  9. Kolodobskii, G. I.; Ostrovskii, V. A.; Popavskii, V. S. Chem. Heterocycl. Compd. 1981, 17, 965. https://doi.org/10.1007/BF00503523
  10. Karnik, A. V.; Malviya, N. J.; Kulkarni, A. M.; Jadhav, B. L. Eur. J. Med. Chem. 2006, 41, 891. https://doi.org/10.1016/j.ejmech.2006.01.018
  11. Jantova, S.; Ruzekova, L.; Stantovsky, S.; Spirkova, K. Neoplasma 1997, 44, 240.
  12. Rubat, C.; Coadert, P.; Couqvelet, J. M.; Tronche, P.; Bastide, J.; Bastide, P. Farmaco 1990, 45, 331.
  13. Muehlebach, M.; Boeger, M.; Cederbaum, F.; Cornes, D.; Friedmann, A. A.; Glock, J.; Niderman, T.; Stoller, A.; Wagner, T. Bioorg. Med. Chem. 2009, 17, 4241. https://doi.org/10.1016/j.bmc.2008.12.062
  14. Kumar, R. R.; Perumal, S.; Balasubramanian, M. Comprehensive Heterocycl. Chem. (III) 2008, 13, 433.
  15. Yranzo, G. I.; Moyano, E. L. Comprehensive Heterocycl. Chem. (III) 2008, 13, 399.
  16. Kiselyov, A.; Khvat, A. Comprehensive Heterocycl. Chem. (III) 2008, 13, 387.
  17. Denisko, O. V. Comprehensive Heterocycl. Chem. (III) 2008, 13, 489.
  18. Souldozi, A.; Ramazani, A.; Bouslimani, N.; Welter, R. Tetrahedron Lett. 2007, 48, 2617. https://doi.org/10.1016/j.tetlet.2007.02.010
  19. Ochoa, M. E.; Rojas-Lima, S.; Höpfl, H.; Rodriguez, P.; Castillo, D.; Farfan, N.; Santillan, R. Tetrahedron 2001, 57, 55. https://doi.org/10.1016/S0040-4020(00)00984-4
  20. Autio, K.; Pyysalo, H. J. Agric. Food Chem. 1983, 31, 568. https://doi.org/10.1021/jf00117a025
  21. OConnell, A. J.; Peek, C. J.; Sammes, P. G. J. Chem. Soc., Chem. Commun. 1983, 399.
  22. Ishiwata, S.; Shiokawa, Y. Chem. Pharm. Bull. 1970, 18, 1245. https://doi.org/10.1248/cpb.18.1245
  23. Druey, J.; Daeniker, H. U. Swiss Pat. 1962, 358, 430.
  24. Daeniker, H. U.; Druey, J. Helv. Chim. Acta 1957, 40, 918. https://doi.org/10.1002/hlca.19570400406
  25. Baron, E. J.; Finegold, S. M. Bailey and Scott's, Diagnostic Microbiology, 8th ed.; Mosby: St. Louis, MO, 1990; p 184.
  26. Druey, J.; Daeniker, H. U. Chem. Abstr. 1963, 59, 11530a.

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